Email is one of the most important communications tools for businesses. When it stops working, people start to get nervous.

While there are many things that a user can do to mess up their email, many of these problems can be resolved with a restart of the software or the computer.

However when the old standby of restarting doesn’t work, it is time for the email administrator to start looking into the issue a bit more deeply.

Here are some of the more common errors found in Outlook 2007 along with some of the ways you can make things right again:

1. Error message that reads: “Cannot open your default e-mail folders. The information store could not be opened.”

This issue can be fixed by first locating Outlook.exe that can be found here: C:\Program Files\Microsoft Office\Office12.

Next, right click Outlook.exe and then click on Properties.

On the Compatibility tab, clear the check box that reads ‘Run this program in compatibility mode’. Then click Ok and restart Outlook.

2. Error message that reads: “Your Microsoft Exchange Server is unavailable.”

This error is a bit trickier to resolve only because there can be many different causes.

No data connection – test your SMTP connection using telnet. If you are unsure how to do this, Microsoft has provided a guide on their TechNet site that walks you through this process: http://technet.microsoft.com/en-us/library/bb123686.aspx.

Office Outlook files are locked – there are times when .ost and .pst files are accidentally, or purposefully, set to read only. Check the permissions of these two files by navigating to:

C:\Users\<username>\AppData\Local\Microsoft\Outlook\ for .pst files and C:\Program Files\Microsoft Office\Office12\ for .ost files. Make sure that neither is set to read only.

Third party applications are interfering with Outlook – many programs, including anti-malware solutions, can interfere with Outlook connecting to the Exchange Server. To check to see if this is the cause, start Outlook in safe mode.

Outlook files are corrupted – this can happen after an upgrade is applied to Outlook. If any of the .dat files listed below are present they should be deleted or renamed.

• Extend.dat – Located in C:\Documents and Settings\<username>\Local Settings\Application Data\Microsoft\Outlook\
• Frmcache.dat – Located in C:\Documents and Settings\<username>\Application Data\Microsoft\Forms\
• Views.dat – Located in C:\Documents and Settings\<username>\Application Data\Microsoft\Outlook\
• Outcmd.dat – Located in C:\Documents and Settings\<username>\Application Data\Microsoft\Outlook\

All the files, with the exception of Outcmd.dat will be re-created. The Outcmd.dat file saves customized toolbar settings so if it is removed these settings will have to be re-applied.

3. Office Outlook will not open personal folders or personal folders do not show up in Outlook.

Personal folders are often the root of many problems related to Outlook. Microsoft has published the Inbox Repair tool, Scanpst.exe, that can be used to scan .pst and .ost files for errors in the file structure. If this is not intact, it will reset the file structure and rebuild the headers.

This tool will only work on the files that reside on your computer’s hard drive, not the files on the Microsoft Exchange Server.

This will also help to resolve the error message: “Cannot open your default e-mail folder. The file c:\users\owner\documents\software info\outlook.pst is not a personal folders file”.

4. Error messages that read either: “The action cannot be completed. The connection to the Microsoft Exchange Server is unavailable. Your network adapter does not have a default gateway” or “Your Microsoft Exchange Server is unavailable”.

This error occurs when Outlook is unsure of the default gateway address. The former is the error message that shows when the Outlook profile is configured automatically and the latter appears when the profile is manually configured. Both have the same fix.

To repair this you will need to edit the registry so clicking on Start and then Run is necessary. Then, enter regedit in the Open box and click OK.

Next, navigate to the registry key: HKEY_CURRENT_USER\Software\Microsoft\Office\12.0\Outlook\RPC. On the Edit menu, point to New, and then click DWORD Value.  Type DefConnectOpts, and then press ENTER. Now, right-click DefConnectOpts, and then click Modify. In the Value data box, type 0, and then click OK.

5. None of the authentication methods supported by this client are supported by your server.

This happens to people when they use their computer in multiple locations. For example, a laptop is taken home and connected to the home network or perhaps a computer is taken on the road. Basically, it comes from authentication rules for the SMTP server.

When this error occurs go to the Account Settings tab and click on Change then More Settings. Now select the Outgoing Server tab.

The option that reads: “My outgoing server requires authentication” and the one that reads: “Log on to incoming mail server before sending mail” should both be looked at. If there is a check in the option box remove it.

5 Common Outlook Errors and How to Fix Them

Free ebook download: Top 10 Most Popular Troubleshooting Posts for Email Administrators

In an age where millions of emails are sent every day it is hard to find someone who hasn’t made a mistake when sending a message.

If you are using Microsoft Outlook and Exchange, you can quickly recall a message and delete unread copies, if you are lucky that is and no one has opened the email. If someone has already opened your errant message, then it’s too late.

Companies have become a bit more cognizant that some employees are just a bit too quick to pull the Send trigger on their mail. To compensate, many have put into place a time delay that gives someone the opportunity to think twice about a message that was sent out and stop it before it is delivered.

Just recently, the New York Times suffered a rather embarrassing incident where they had planned to send a few hundred emails out to some of their subscribers offering them a discounted rate if they did not cancel their subscription. Instead the message went out to over 8 million people.

That was mistake number one.

This was then followed up by a message that read:

“If you received an email today about canceling your NYT subscription, ignore it. It’s not from us”

sent out via Twitter. So they were blaming the mistake on someone else, a spammer perhaps.

But, as it was later discovered, the Times was the guilty party. They did send the initial message and then pawned off the responsibility.

Where the mistake hurt

This gaffe wound up costing the Times. Not only was their reputation hurt, but so was their bank account.

Since a discounted rate was promised to the few hundred who were thinking of cancelling their subscription to the Times, other customers felt slighted. Their loyalty, so it seemed, accounted for little reward.

To make up for it, the Times extended the discount to everyone who received the errant email, but only for part of a day. By the afternoon of their offer, they had put a halt to the discounted rates. This decision then led to a Twitter account called @NYTSpam that made fun of the error fully disclosing that it was a:

“Parody account. Not affiliated with @NYTimes or actual spammers — just sick of bad digital strategy.”

The account currently has over 200 followers.

The Times is not alone when it comes to paying the price for a bad email going public. These things actually happen all the time. But when it happens to a small business, we don’t really hear about it.

To keep the lid on scandals and humiliation that can be suffered due to email, it is important that you cover certain things with your employees.

Anyone who emails on behalf of the company should understand the following:

1. Never send an email when you are angry or emotional. This leads to things being said that you may want to take back.
2. Write, edit, send. Never type out an email and hit the send button without reading it over. Not only for spelling and grammar errors that could hurt your reputation, but also for the tone of the email. People read into things and if the tone is not what you intend it could lead to problems later.
3. Check your list. This ties in directly to the Times situation. Make sure that you are sending your email message to the right people. This becomes more important with so many organizations automatically populating the TO and CC fields as you type names. Make sure that you don’t rely simply on the names suggested to you. Be careful using the Reply to All as well.
4. Never punish or praise in an email message. Not only can the content of an email be misconstrued because of a lack of emotion, but it can also become evidence or public record. If you fail to follow human resources procedures, email can be a pretty solid form of documentation.
5. Don’t share company secrets via email. Whether they be financial, trade or even personal secrets they should never be relayed through an email message. It is far too easy for someone to accidentally, or purposefully, forward that message on to others.

Common Mistakes When Sending Emails

Free ebook download: Top 10 Most Popular Troubleshooting Posts for Email Administrators

When starting out, many small businesses set up their email using one of the free accounts available to them. Services like Gmail by Google, Hotmail from Microsoft or Yahoo!’s mail service, provide a working email address with almost no maintenance for a business just getting its feet wet.

However this may not be the best way to make a first impression with your potential customers.

Listed below are seven reasons why you need to ditch the yourcompany@freeemail.com and go with an address that better reflects the image you want your company to have.

1. Free email looks less professional

People associate free email services like Gmail or Hotmail as a personal accounts. Businesses, on the other hand, should have an email address that looks more professional. In fact, a study by Visible Logic in Amsterdam found that 70 percent of people view email messages coming from free email services as less professional when used by a business.

2. Free email looks spammy

Over the years, people have been burned so often by spam that they have become very adept at spotting shady looking emails in their inbox. One way to spot an email that may have malicious intent is by looking at the address. If you email address doesn’t look legitimate, your messages may be overlooked by overly cautious recipients.

3. Free email looks cheap

When people receive an email from your company and it has the @freeemail.com trailing it, your company looks cheap. For less than five bucks a month, you can set up an email address with your company’s domain. Sometimes you can even get a few of these for free when you host your company’s website. Customers who see that you are unwilling to spend a few dollars on this are often left to wonder what else your company may be skimping on.

4. You lose credibility when you use free email

A legitimate, professional looking email address tells your customers that you are here to stay.

Not only that, but having multiple email addresses such as: info@yourcompany.com, sales@yourcompany.com or service@yourcompany.com shows others that you are a well structured organization. The impression one gets when there is one, free email as the sole contact is that one person is handling everything for a company. This may scare larger clients away for fear that the company cannot handle their needs.

In today’s business atmosphere, trust is everything. Especially when it comes to online sales. Every little thing your company can do to establish trust and credibility will help your business grow.

5. Free email is less secure

Remember the old saying: there is no such thing as a free lunch? Well that applies to email as well.

True, Google, Yahoo!, Microsoft and the other free email providers do everything they can to make sure that their email services are as secure as possible, but things can slip through the cracks.

To pay for “free” email, users are subject to advertisements. While these help pay for the servers and storage space, they also have been linked to spam and hijacking. There have been several cases where businesses have had bank accounts and other confidential information compromised by cyber criminals who intercept email messages of companies that use free email services.

6. Free email may put you out of compliance

Nowadays, there are regulations and laws that govern so many industries and their record keeping that many large companies have entire legal teams dedicated to just compliance related issues.

But smaller companies are not immune to compliance. Companies of all sizes need to be aware of HIPPA when it comes to healthcare, PCI DSS when dealing with credit cards, and CAN-SPAM Act when it comes to marketing.

Free email likely does not offer you the tools required to be in compliance with any of these, or the many other, laws or regulations for email use.

7. You miss out on marketing your brand

Having your website’s domain name in every email you send out gives you the opportunity to build your company’s brand. Info@yourcompany.com puts your web site address in the minds of your customers. They know where to turn to when they need your services because they are so used to seeing your domain in every communication from you.

7 Reasons to Ditch That Free Email Address

Free ebook download: Top 10 Most Popular Troubleshooting Posts for Email Administrators

Users of practically every supported version of Windows, whether desktop or server, 32 bit or 64 bit, and even the low attack surface Windows Server Core should immediately review Microsoft Security Bulletin MS11-100 and begin testing and deployment of this patch as soon as possible. The patch, covered in KB2638420 addresses four vulnerabilities in the Microsoft .NET Framework, including 1.1 SP1, 2.0 SP2, 3.5 SP1, 3.5.1, and 4. Three of the four were privately reported, while the last one has been publicly disclosed.

In a worst case scenario, an unauthenticated attacker could send a specially crafted request to an unpatched server, and gain elevated privileges which could then execute remote code on the impacted server. Exploiting this vulnerability requires that the attacker be able to register an account on an ASP.NET site, and know an existing username. Of course, when so few follow recommended practices and rename the Administrator account, or use common accounts like Admin, Guest, etc., this doesn’t present too high a bar for any site that allows user registrations.

In all, four separate CVEs are addressed by this update, including:

1. Collisions in HashTable May Cause DoS Vulnerability – CVE-2011-3414
2. Insecure Redirect in .NET Form Authentication Vulnerability – CVE-2011-3415
3. ASP.Net Forms Authentication Bypass Vulnerability – CVE-2011-3416
4. ASP.NET Forms Authentication Ticket Caching Vulnerability – CVE-2011-3417

KB2638420 replaces several earlier patches that were released to address some of these vulnerabilities. The first, involving collisions in HashTable, can lead to a denial of service, which can be just as significant an impact to users as any other kind of attack. Exchange admins running Edge Transport Servers and/or Client  Access Servers exposed to the Internet should be aware of this and deploy this security patch as soon as possible. All Exchange server roles require the .NET Framework 3.5 SP1 and are therefore vulnerable, so all Hub Transport, Unified Messaging, and Mailbox servers should also be patched.

As with all patches, you should test this in your lab environment before deploying to production, and follow your appropriate change control processes, but that does not mean you should wait until after the New Year to start evaluating this patch. Microsoft released it out of band (instead of waiting for the normal patch Tuesday in January) because this does address a publicly disclosed vulnerability, and the combined impact should a server be successfully exploited is so critical. When patching Exchange, apply this patch to your server roles in the following order:

1. Edge Transport
2. Client Access
3. Hub Transport
4. Mailbox
5. Unified Messaging.

Microsoft Releases Critical, Out Of Band Update

Free ebook download: Top 10 Most Popular Troubleshooting Posts for Email Administrators

Users interested in deploying a hybrid configuration have been looking forward to Exchange 2010 SP2 for months so they could take advantage of the new hybrid configuration wizard included with SP2. That wizard takes dozens of manual steps and automates them in a simple to follow wizard, which we discussed in this article a few weeks ago.

While the hybrid configuration wizard is a great improvement in setting up an Exchange system with some mailboxes on premise, and others with a cloud service provider, it seems a small glitch made it through to the release of SP2. It seems that many customers are running into issues using PKI certificates that were previously issued and which worked without a problem in Exchange 2010 RTM and/or SP1.

There is a TechNet article called Understanding Certificate Requirements for Hybrid Deployments that details what you should do when creating a certificate for hybrid deployments. The article (as of the date this post was written) only indicates SP1, but includes the steps I followed when creating a certificate for hybrid configuration. The article discusses the use of a SAN certificate, but does not discuss using a wildcard certificate, and here’s why this is a good thing. When you run the wizard to set up hybrid configuration, the wizard parses the CN of your certificate and attempts to set up a Send Connector for the SMTP encryption between your on-premise and your remote Exchange infrastructure. If it encounters a value like *.example.com in the CN, the wizard will error out because that is an invalid name for a Send Connector. Here’s what the error looks like:

Update-HybridConfiguration

Failed

Error:

Updating hybrid configuration failed with error
'Subtask Configure execution failed: Configure Mail Flow
Execution of the New-SendConnector cmdlet had thrown an exception.
This may indicate invalid parameters in your Hybrid Configuration settings.
Cannot process argument transformation on parameter 'Fqdn'.
Cannot convert value "*.example.com" to type "Microsoft.Exchange.Data.Fqdn".
Error: ""*.example.com" isn't a valid SMTP domain."
at System.Management.Automation.PowerShell.CoreInvoke[TOutput]
(IEnumerable input, PSDataCollection`1 output, PSInvocationSettings settings)
at System.Management.Automation.PowerShell.Invoke(IEnumerable input,
PSInvocationSettings settings) at System.Management.Automation.PowerShell.Invoke()
at Microsoft.Exchange.Management.Hybrid.RemotePowershellSession.RunCommand
(String cmdlet, Dictionary`2 parameters, Boolean ignoreNotFoundErrors)'.
Additional troubleshooting information is available in the Update-HybridConfiguration
log file located at C:\Program Files\Microsoft\Exchange
Server\V14\Logging\Update-HybridConfiguration\HybridConfiguration_12_16_2011_5_58_59_634596119396658235.log.
Exchange Management Shell command attempted:
Update-HybridConfiguration -OnPremisesCredentials
'System.Management.Automation.PSCredential' -TenantCredentials 'System.Management.Automation.PSCredential'

So, what can you do to move past this? Two choices are available. The first is to not use a wildcard certificate. I know, I know, wildcard certs are awesome, solve a ton of other headaches, and security concerns notwithstanding, are a dream come true. However, since the * in the wildcard cert is what causes the wizard to hurl, stick with a SAN certificate if you need a cert that can validate more than one name. The second is to get the fix from Microsoft. If you already have a wildcard certificate, this is the more economical way to go. You can wait for RU1 that is due to release in January 2012, or you can contact Microsoft for a hotfix.

Even with this little “issue” SP2 is a great improvement over SP1, and if you are planning a hybrid deployment, it is still the way to go. A regular, SAN, or UC certificate is far less expensive than a wildcard, so this may not be an issue for you anyway, but if you already have a wildcard cert, your fix is a free phone call away.

Certificate Problems with Hybrid Configuration in SP2

Free ebook download: Top 10 Most Popular Troubleshooting Posts for Email Administrators

You’ve probably seen this before. A user opens a help desk ticket because every time they try to send an email to someone, it bounces. That someone could be a co-worker using the same email system, or it could be a customer on an external email system – it doesn’t matter. When the user replies to an email sent from the other person, the reply is delivered flawlessly. But when the user tries to create a new email, it bounces.

You try to send an email to the remote person and it is delivered correctly. You use message tracking to try to run down the problem with the email, and you might not even find it (if you are searching on the recipient address that is…which is a hint).  It’s not until you have the users actually showing you what they are doing that you realize they have a bad address in their nickname cache.

The nickname cache, which provides Outlook’s handy auto-completion when you start to type a name or an email address into the TO: or CC: or BCC: boxes in a new email, is used both to perform automatic name checking and to perform auto-completion. It is also lets you start to type “Cas…” into the TO: box and pulls up casper.manes@example.com so you don’t have to type out the complete email address. The problem comes up when a recipient’s address is wrong, or changes, and your client holds old or bad information.

To fix this, you can remove entries one at a time, or you can purge the cache completely. If you have recently changed your internal addressing standard, or migrated to a new system, I tend to just purge the whole thing so folks have to go to the GAL for fresh information. They will rebuild their cache soon enough, but if it is just a one or two addressee issue, removing individual entrees is easy enough.

To remove a single entry:

1. Start typing the email address, until autocomplete provides choices, like shown below.
   
2. Click the X to the right of the name to delete it from the cache.

To completely remove the cache:

1. Click File, Options
2. Select the Mail tab
3. Scroll down to “Send messages” and click the “Empty Auto-Complete List” button.
   

Alternatively, you can launch Outlook from the Run dialog using
Outlook.exe /CleanAutoCompleteCache

Protip: using that cmd line in a login script is a convenient way to clear all users’ caches after a migration.

Removing bad entries will force the user to go to the GAL, or use a personal contact, or just type the email address in longhand, which will update the nickname cache with the proper email address, and that means a problem solved.

Troubleshooting Outlook Auto-complete

Free ebook download: Top 10 Most Popular Troubleshooting Posts for Email Administrators

A team of researchers from IBM and Microsoft recently published an article detailing their studies about email sorting and searching called “Am I wasting my time organizing email? A study of email refinding”. The researchers studied the email sorting and searching activities of 345 users and came up with a surprising conclusion – users who sort email might be wasting their time.

The researcher team was made up of Steve Whittaker, Tara Matthews, Julian Cerruti, and Hernan Badenes of IBM, and John Tang of Microsoft used a web-based email client called Bluemail to study the actions of the study participants. They coined three phrases to define the actions of email users. Preparatory activities are those actions users take to sort and file messages, including the creation of folders, moving emails into those folders, tagging messages, and setting up rules to support the other actions. Opportunistic methods for finding messages use search and conversation threading to locate messages. Refinding actions are those that users take to look for a message that they have already seen in their inbox, whether that was tagged, sorted, or just allowed to drop down the list.

They analysed the email behaviours of the study members to see how much time was spent on each activity. They found after studying the email habits of those users over time that users who spend significant time creating folder structures and sorting email invest more time in these activities than they save. These efforts might seem like a good idea to the users, but the time spent exceeds the time they saved performing. Those users who rely on tags, threaded conversations, and simply use search to find messages spend less time overall on refinding.

With threaded conversations becoming more common in email clients, and tagging/categories available in many packages, opportunistic methods are an option many of us can try out if we aren’t already. Outlook 2010 doesn’t do tagging by that name, but you can categorise messages using any of the included colours, or you can create your own categories and easily apply them to messages manually, or using a rule.

I find that personally, I have a split personality when it comes to email sorting. At work, I have a fairly extensive set of folders for sorting email; including folders for distribution lists I subscribe to (or have been subscribed to,) folders for things I want to keep long term like HR, expense reports, clients, etc. I also use a few rules in Outlook to automatically sort the distribution list emails into their appropriate folders. However, my personal email account is a Gmail account, and I don’t even tag emails in there. I do delete the obvious trash, and the one-off emails, but I have thousands and thousands of emails going back to 2001, on that “off chance” I might need one again. And while I have needed older emails plenty of times, I just do a quick search and find it in the results.

Interestingly enough, I do exactly that in Outlook on my work account too. I just type in the search and then click the “Try searching again in All Mail Items” rather than going to a particular folder, even when I know which folder it will be in. I guess maybe I am wasting my time.

What about you? Are you a “frequent filer” or more of a “Keep ‘em all and let search sort ‘em out” kind of person? Leave a comment and let me know what works for you. And for those of you with time on your hands, here’s a link (new window, PDF) to the study.

Study Says Sorting Emails Is a Waste of Time

Free ebook download: Top 10 Most Popular Troubleshooting Posts for Email Administrators

There was a time when using PST files were thought to be the solution to file storage problems. Getting emails out of the user’s mailbox and onto a shared repository not only freed up email inboxes from increasing file sizes, but also gave admins a central location in which all emails could be backed up and archived.

Add to these benefits the fact that PST files could be separated so emails related to a project, client, subject, etc could be stored and archived separately, and many would think that this solution was all that an IT department would need to manage their archiving and storage needs.

Of course PST files aren’t a panacea; they have many problems associated with them.

Working offline

More and more frequently, workers find themselves working remotely. When this happens, they don’t always have access to network resources so they find themselves working offline. This makes accessing PST files stored on a network device difficult, if not impossible, to use.

Workers who need to refer back to emails in their personal folders are pretty much out of luck.

Another, more common situation, arises when PST files are stored on a desktop computer at the home office and a remote worker is using a different computer; let’s say a laptop at home.

This user could not access his or her PST files if they cannot access that desktop computer where the file is housed. Now you may wonder why anyone would keep their PST files on the local computer as opposed to a shared network resource, but the scenario is actually quite common.

In fact, it was considered a best practice since Exchange 4.0.

According to the Technet blog:

“A .pst file is a file-access-driven method of message storage. File-access-driven means that the computer uses special file access commands that the operating system provides to read and write data to the file.

This is not efficient on WAN or LAN links because WAN/LAN links use network-access-driven methods, commands the operating system provides to send data to or receive from another networked computer. If there is a remote .pst (over a network link), Microsoft Outlook tries to use the file commands to read from the file or write to the file, but the operating system then has to send those commands over the network because the file is not on the local computer. This creates a great deal of overhead and increases the time it takes to read and write to the file. Additionally, the use of a .pst file over a network connection may result in a corrupted .pst file if the connection degrades or fails.”

Bad files

Anyone who has worked with PST files knows that they have a tendency to become corrupted or damaged. There is an entire industry dedicated to developing tools to help email administrators fix damaged PST files, and Microsoft themselves have published a number of tools to help fix specific problems.

These problems can occur due to hardware failures, such as:

• A failure in the storage device
• A power failure
• Failure in a networking device
• Failure in the network infrastructure

Of course, the software itself also has been known to create problems:

• Incorrect file system recovery where PST data is incomplete or incorrect
• Malware infections that damage PST files
• Outlook being terminated abnormally
• Deficiencies in Outlook itself

Regardless of what caused the problem, if you encounter damaged PST files it costs money to repair them. It can cost even more if you are required to provide information from them but can’t because they are corrupted.

The intent behind personal storage tables makes perfect sense. However, in practice email administrators need to find a better solution if they want to stop wasting time with the hassles presented to them by Outlook’s PST problems.

Solutions that are made to be stored on network file stores and less likely to be corrupted by common tasks, not only make life easier for the IT department, but legal departments as well, since accurate, reliable information can be provided when it is requested, not when a company eventually finds a specialist to piece everything together.

Two Big Problems With PST Files

Free ebook download: Top 10 Most Popular Troubleshooting Posts for Email Administrators

I’m not saying that email is taking a bad rap these days, but there are many people out there who believe that email’s days as the reigning king of workplace communication are numbered.

With more companies opening up the doors to social media communication, text messaging and instant messaging, email is no longer the only method used to send electronic messages out to co-workers and customers.

One of the biggest reasons that email’s popularity is slipping with some users cannot be pinned down to any one particular reason. Actually, there are many collective reasons that people are beginning to turn away:

• Reading and answering email is viewed as a distraction
• Too much spam or junk email
• People don’t respond in a timely fashion
• It is hard to have a real time conversation

While many email users agree that these are some of the biggest problems with email, the fact remains that this method of communication is still the most widely used tool online every day because people are familiar with it and it works.

Making the most of email

There was a time when people thought email was the greatest business tool to ever come about. During that honeymoon phase, people could see no wrong when it came to sending and receiving electronic messages this way.

Like any other technology, after a while you start to notice the problems it has, your patience grows short and you start looking for the next best thing.

But you can rekindle your company’s romance with email using a little bit of guidance to help your users recapture the magic they felt when they first heard that ring of “You’ve got mail!”

Use the subject line wisely

All too often we are vague when it comes to writing subject lines. We are all guilty of writing things like: “please read”, “for review”, or even leaving the subject line blank. When we do that, we really shouldn’t be surprised if our message is not treated as one that is important. In fact, we should be lucky if we get any response at all.

Users should make their subject lines work for them. For example, “Need feedback on sales presentation by Friday” has all the makings a subject line that demands attention and a response.

Keep messages on target

Like anything else on a computer screen, people tend to scan rather than read big blocks of text.

When writing emails, it is important to break the message’s content in to small, digestible pieces for your readers so that they are more inclined to read the entire email, not just the parts they think might be important.

It also helps to keep emails focused on one topic. Teach users to send separate emails for different topics to keep messages shorter.

Address emails immediately

One of the biggest complaints users have regarding email is how much time it takes up. Most of this is their fault.

Commonly, a user checks his or her email first thing in the morning. Unfortunately they don’t often do much with these emails other than read over them.

By getting your users in the habit of dealing with email messages right when they open them up, they will find that the inefficiency myth surrounding email can be put to rest.

This doesn’t mean that your co-workers have to respond to each message immediately, but they should know that when they open a message up they need to reply, file it appropriately, delete it, or print it out for later. Never ignore the email and wait until later on in the day to address it.

Set a schedule

Most companies have a written policy as to how often users need to check their email. Some will even tell employees when they need to check them throughout the day.

While many find this to be a bit overwhelming, there is a reason. When people develop a habit of checking their email messages at certain times throughout the day, they become much more productive. The reasons are two-fold.

First, you are not distracted by constantly checking your email inbox. Surprisingly enough, constantly opening Outlook or Gmail throughout the day takes a great deal of time away from more productive activities.

The second reason is that a set schedule forces users to deal with incoming messages promptly. This helps business get done much more efficiently than if a message sits unread for days on end.

Although email has taken some knocks over the years, statistics show that people are still using it in increasing numbers – so it’s certainly not going anywhere. We can, however, give it that new car smell once again by reminding others how to best use it in the workplace.

Making Email Pleasant Again

Free ebook download: Top 10 Most Popular Troubleshooting Posts for Email Administrators

In Understanding Email Encryption Part 1 I covered not only why encrypting email is important, but also the two different types of email encryption: asymmetrical and symmetrical.

There was another section that briefly mentioned some of the barriers that impede buy-in from management when it comes to an encryption solution. But these were only touched upon.

Unfortunately when it comes to making a pitch for encryption, those who understand the need for it are an easy sell. Those who either don’t understand it or see the need for it often cite one or more of these stigmas that are attached to email encryption as reason to avoid it.

Should you find yourself being stonewalled when giving your reasons for email encryption, here are a few points you can make to counter any disbelievers.

Of course the consequences that come from disputing your boss in front of others is something that encryption can’t protect against, so use them at your own risk.

Encryption makes us look paranoid

In the previous post I quoted a survey respondent as saying: “normal people don’t encrypt normal email messages” when asked about adopting encryption for email.

The problem is that society does tend to raise an eyebrow at those who act paranoid. Let’s be honest here, they are outright ridiculed.

And no one wants to be made fun of. But that is playground thinking. As a customer, client or employee I want to know that my personal or confidential information is being protected. Email encryption can make me look silly if I am sending a joke to a friend and I use DES cryptography, but if account information is being sent from my bank I want to see a bit of protection put in place.

One way to counter this is to ask, “would you rather someone think you a bit paranoid, or would you rather be in the news like the Oak Ridge Laboratory, CitiGroup, Sony, Target, Chase, etc.”

Encryption is too complicated for most users

15 years ago, email was too complicated for most users. There was a time when the telephone was complicated technology.

And yes, there was a time when cryptography for email messages was quite a bit of work but now it is rather simple and solutions operate seamlessly with your company’s email client.

Outlook offers two separate methods of encrypting email messages. You can encrypt a single message, using 3DES by going to the Message tab in the Options group and click on the Encrypt Message Contents and Attachments button.

After that you simply write your message and send it on its way.

Encrypting all messages can be done as well but that requires all recipients to have your digital ID to decrypt the contents.

Still, that doesn’t seem too difficult now does it?

Encryption is too expensive for us

Another stigma is that encryption is for large companies, not small or medium sized businesses – this isn’t entirely accurate.

Sure, an organization can spend a good deal of money on an expensive appliance that requires add-ons and plug-ins. But you don’t have to spend that much.

With Software as a Service models, even the smallest company can purchase a service contract for only what they need. Be it one user or a thousand.

There are even companies that cater these services to smaller organizations specifically to keep costs within reason.

Software as a Service solutions can also help negate the belief that encryption will be too much of an undertaking for your IT staff as well. Since the company is buying the service, there is nothing for the IT people to set up, configure, troubleshoot, monitor, etc.

Encryption, like any other technology, has changed over the years. But so has the need for it. There was a time when email wasn’t such a lucrative target for attackers. There was a time when regulations mandated certain security baselines be put in place. There was a time when using encryption required a Master’s Degree in Computer Engineering. But all that has changed. Let your company know it’s about time their mentality regarding protecting email messages does as well.

Understanding Email Encryption (Part 2)

Free ebook download: Top 10 Most Popular Troubleshooting Posts for Email Administrators

If you have followed TheEmailAdmin for any length of time, you have probably gotten the idea that PST files are not anything we’re fans of. We’ve discussed the adverse impact to performance, alternatives to using PST files, and that with Exchange 2010 and Microsoft’s Large Mailbox Vision, there’s really no reason to have PSTs anymore.

And yet, time and again, as a consultant I find PST files on users’ hard drives, in their home directories, and even in team folders, accessed by large groups of users. Once, I even found a user storing their PST file in their Dropbox folder so that they could access it from multiple machines, but they couldn’t figure out why Outlook threw an error every time they tried to open their PST file.

Just in case you don’t want to read those great articles I linked to above, and you’re also not sure what the big deal is about PST files, consider the following. PST files were originally introduced by Microsoft as a storage mechanism for email downloaded from POP3 servers, where the messages would not be stored long term on the server, and the PST files would be kept on the local hard drive. Because accessing PST files over a network connection requires serialized RPC calls that the file server hosting the PST must then access on the file, performance can be up to four times slower, the risk of file corruption is high, and the file server can become unresponsive to other clients while processing read/write requests to the PST – impacting all other users, not just those storing mail in network PSTs.

So how should you go about eradicating the scourge of the email high seas? There are four things you should go about doing now:

1. Whether you are planning an upgrade to on premises Exchange 2010, or moving your email to the cloud, remember that storage is orders of magnitude less expensive today than it was even a few years ago. Size your deployment so that your users have mailboxes large enough that they don’t need to move old messages to a PST file.
2. Implement an email archiving solution to provide long term storage for those email packrats. Of course, there are several benefits to an archiving solution including support for compliance efforts, enabling search, and preserving intellectual property, but since a PST is normally used to archive old messages, having a centrally managed archive eliminates the need for PSTs, lets the email admin manage the archive centrally, and offers all the other benefits to the business. Many archiving programs include tools to import the contents of PST files to the archive.
3. Use the Exchange Management Shell command New-MailboxImportRequest to import PST files into those larger mailboxes you set up for your users. You can read more about that cmdlet here.
4. Look for the upcoming tool from Microsoft called the PST Capture Tool. While the New-MailboxImportRequest tool is designed to import known PST files at the cmd line, and most archiving programs PST import tools require you to provide the path to the PST file you want to move to an archive, the PST Capture Tool is being designed to seek out PST files across the network, and to automate the process of importing them into either on premise Exchange, or to Office 365.

Even if you are planning a move to another provider, or using a third party archiving solution, using this tool to automate the import of PSTs into your on premise mailbox prior to your migration, or to simply provide a list of existing PST files across all your shares, will make eradicating those pesky files much easier than a manual search, or kludgy batch file. Watch this blog for an update when the tool is released.

Your Mission: Seek and Destroy all PSTs

Free ebook download: Top 10 Most Popular Troubleshooting Posts for Email Administrators

Some estimates peg the average amount of time a typical knowledge worker spends on email each business day at three hours. If the typical readers of this blog are anything like me at all, we can probably double that number, and add six or more hours each Saturday and Sunday to that.

Inbox overload can become a serious problem for information workers, whether they are in IT or not. Next time you are in a restaurant with your family, take a look around you to see how many adults are on their smartphones at any point in time (teens texting or checking their FB feeds don’t count). Scary, isn’t it?

To try to combat this trend and buy back a little bit of my day, I have made some changes to the way I work with email. Some of these may work for you too, others may not, but if you get a useful tip from even one of these, then it’s worth the time I took to write this post and for you to read it.

The first ten tips come from http://emailcharter.org/. Let me paraphrase them here, but I want you to check out that link after you are done with this post.

1. Respect Recipients’ Time

Bottom line it for me, and use bullets to call out points.

2. Short or Slow is not Rude

Concise correspondence is a good thing. Email was never designed to be instant. If you need an urgent answer, either tag the subject appropriately, use IM, or call me.

3. Celebrate Clarity

Make your subject clear, change it or start a new email thread if the subject changes, and tag it with things like Urgent, FYI, Action, or Question to let me know how to prioritize messages.

4. Quash Open-Ended Questions

If the answer to a question will spawn more questions, call. If you must include a series of questions, break them out in bullets or numbers to make them easy to see and to answer.

5. Slash Surplus Cc’s

Don’t Cc someone unless they really need to be participants in an email. You can always forward a summary of the thread when there is useful information.

6. Tighten the Thread

Keep an email thread on track, and cut out unnecessary information when you can.

7. Attack Attachments

Ever gotten an email with an attachment that should have been the body of the email? Avoid graphics in signatures too, especially if they are linked.

8. Give these Gifts: EOM NNTR

If your email message can be expressed in half a dozen words, just put it in the subject line, followed by EOM (End of Message). This saves the recipient having to actually open the message. Ending a note with “No need to respond” or NNTR, is a wonderful act of generosity.

9. Cut Contentless Responses

NEVER reply all unless you really need Everyone to see a reply. Don’t reply with a simple “yes” or “I agree” or “boo-yah” unless the sender specifically asked for a reply. Polite conversation says to say “thank you,” or to respond with “you’re welcome” but the same need not apply to email when that is the only thing to convey.

10. Disconnect!

Unless you are on call, or use email alerts for time sensitive things, turn off alerts in your email client, and set up your smartphone to only retrieve email manually. Check when you hit a good stopping point in whatever you are doing instead of letting yourself be interrupted every few moments. Just be sure you let your colleagues know to call you if something is critical.

11. Use fewer sentenc.es

Take a look at http://five.sentenc.es and see if that approach might work for you. By keeping your communications brief, you save yourself and your colleagues time. I’m digging it. There’s also smaller versions if you can be really concise.

By the way, you may be amazed at how much longer your smartphone battery lasts if you set it so it only fetches email when you check, instead of pushing email to you. You might even amaze your family with how much more connected to them you become! I hope you find at least one of these tips useful. I’ll check my email sometime later to see if anyone comments, but I won’t be listening for a new message notification.

11 Tips to help you avoid inbox overload

Free ebook download: Top 10 Most Popular Troubleshooting Posts for Email Administrators

Microsoft’s newly launched Office 365 offers powerful, intuitive controls for businesses looking to deploy a cloud-hosted collaboration and messaging solution.  I was able to get my own trial account activated in just 10 minutes, faster than any hosted Exchange providers that I’m aware of.  In addition, the presence of a free 30-day trial means that businesses and individuals can experiment with – or even deploy – various components of the service without having to part with a single cent.

As I’ve explained in Why Office 365 is good for Exchange Administrators, Office 365 can actually help to bolster the popular of Exchange Server; enhancing the career prospects of experienced Exchange administrators in the long-term.  Moreover, many of the reasons to consider an on-premise deployment of Exchange Server remain just as relevant today.  This includes a greater choice of anti-spam and anti-malware solutions, heightened confidentiality, compliance, as well as increased backup and archival options.

Companies on the fence about deploying Exchange or new businesses lacking the budget for on-premise Exchange Server will definitely want to start off with Office 365.  Depending on individual requirements, businesses can migrate to a full-fledged Exchange Server at a later date.  To assist administrators who may be thinking of starting off their Exchange deployment on Office 365, I shall be exploring the capabilities of the various plans today with a specific focus on Exchange Server.

Office 365 for professionals and small businesses

Positioned towards professionals and small businesses, Plan P is touted as a plan that offers value-for-money.  It is easy to see its attraction when one considers its Exchange capabilities, as well as the presence of SharePoint Online and Office Web Apps.  The downside is lower levels of support: don’t bother calling Microsoft when you encounter any problems.  Moreover, note that Plan P has an upper limit of 50 user licenses, and does not support Active Directory Sync.(Though the Plan P product page says “fewer than 25 users”, it does not stop users from buying up to 50 user licenses).

According to the official FAQ, a company growing beyond 50 users will need to cancel their Plan P and manually switch to a Plan E. You heard it right; there is no automatic migration for businesses that outgrow Plan P.  Finally, do note that Plan P does not officially support what it calls “vanity” domain (yourname@yourdomain.com), but defaults instead to yourname@yourcompanyname.onmicrosoft.com.  There are a couple of workaround strategies fortunately, which I shall outline in my next article. And yes, Plan P includes premium antivirus and anti-spam filtering with Microsoft Forefront Online Protection for Exchange

Despite its shortcomings, its low price of US$6 per user per month makes Plan P a compelling offering indeed.  The Plan P1 trial includes 10 user licenses.  You can read more about Plan P here.

Office 365 for midsize businesses and enterprises

Plan E comes in various configurations that range from E1, E2, E3 to E4.  Priced at US$10, US$16, US$24 and US$27 per user per month, the various offerings under Plan E include the license rights to access on-premise deployment of Exchange Server, SharePoint Server and Lync Server – more about possible deployment scenarios another time.  E1 excludes online document viewing and editing capabilities with Office Web Apps, while E3 and E4 include the desktop edition of Office Professional Plus.  Do note that a trial is only available for Plan E3, which includes 25 user licenses.  You can read more about the various offerings under Plan E here.

Other Online Exchange options

Businesses that require only Exchange Server services will be interested in the “Kiosk Worker Plans” called K1 and K2.  Both plans offer 500MB of mailbox storage and are priced at just US$4 and US$10 respectively.  It is important to note that both plans offer the Outlook Web App as the only interface to standard Exchange services such as email, calendar, contacts and the company directory.  Microsoft Outlook is not supported, although POP access is. The slightly pricier K2 plan comes with the ability to make basic edits to documents with Office Web Apps.

Finally, administrators or individuals interested in Exchange Online-only plans may want to check out the various plans tucked away here.  Exchange Online is offered at just US$5 and US$10 per month and includes access via PC (Microsoft Outlook), Exchange ActiveSync (EAS) and Outlook Web App.  A final Exchange Online Kiosk plan mirrors the K1 plan by doing away with Outlook and EAS support (no contacts and company directory too) for a rock bottom price of just US$2 per user per month.

Have you given Exchange Online in Office 365 a spin yet?  Feel free to share your experiences.

A Closer Look at Exchange in Microsoft’s Office 365

Free ebook download: Top 10 Most Popular Troubleshooting Posts for Email Administrators

You must have heard about the launch of Microsoft’s Office 365 last week, which promised end-users and businesses alike with a way to attain “anywhere access to email, documents, contacts, and calendars”.  Understandably, the availability of a Microsoft-supported and run Exchange offering may have resulted in some amount of anxiety with some administrators.

To get a better feel of Office 365, I spent some time last weekend figuring out the various packages, and have also signed up for a trial Office 365 account to get a hands-on feel of Microsoft’s latest – and arguably best - cloud-based offering.  Today, I want to share my experiences as to why Office 365 may actually be good thing for Exchange Administrators.

Maintains the popularity of Outlook

It’s no secret that competitors such as Google have been making steady inroads into selling the concept of Google Apps to educational institutions and businesses.  While it is plausible that some of these lost businesses would never have opted for Microsoft Exchange even in the absence of Google Apps, the logical conclusion is that more than one company must have defected as a result.  Moreover, the fight is an unequal one, given the inherent strengths of cloud computing when it comes to server maintenance and up-front cost.  Hosted Exchange evens the ground somewhat, though the specifics in terms of supported features and the ease of setup varies depending on the actual provider.

Office 365 is brilliant in that it takes the fight fully back to Google Apps by adding an online office suite and collaborative services in a standard, well-integrated interface that businesses can manage with ease.  Moreover, Office 365 maintains the popularity of Outlook by allowing small and large companies alike to tap into the full capabilities of Exchange at a competitive price tag. As you can see, these factors will only help entrench the popularity of Exchange with businesses in the long run.

Management still required

Administrators concerned that Office 365 may threaten their roles will be happy to know that administrative tasks such as user creation and service provisioning are still required – and supported, in Microsoft’s Office 365 offering.  Enough said.

Can be used to supplement an on-site Exchange deployment

I have not fully explored this aspect of Office 365 yet, but you may be interested to know that Microsoft caters to scenarios where businesses may want to deploy a mixed on-site and cloud architecture.  I’ll write more about the various mixed mode configurations in a future article.

Ability to quickly test out Exchange and SharePoint

In the past, decisions on whether to proceed with Exchange could take a long time in coming – completely understandable given the steep costs of acquiring the hardware and licenses for a new deployment.  This is further complicated by the uncertain return on investment and unknown productivity gains.  With Office 365, businesses can quickly set up a trial account for a more accurate assessment of whether Exchange and SharePoint have what it takes to meet business needs.  With zero setup costs, businesses on the fence about Exchange are now far more likely to consider this option versus “Exchange-compatible” email server products.

Deploy Exchange?  Sure, I’ll be ready in 10 minutes

Imagine this: You are interviewing at an ultra-secret start-up that has just secured a huge amount of funding from private investors.  The interviewer (and founder) wants to deploy Exchange to support the 20 new engineers he’s just hired earlier today.  He’s rearing to go, and he wants to launch the product, like, yesterday.  How soon can you get a working email system up?  Money is not an issue.

Now, you can ramble on like a typical administrator about the various merits of on-site or hosted Exchange deployments and quiz him endlessly with questions about collaboration needs and eventual size of his company.  Then call up a couple of companies, get three quotes, factor in delivery times that range from a couple of days to weeks.  In the meantime, you can apply for a dedicated Internet connection; add in a couple more days for installation and configuration… you get what I mean.

Or you can tell him you can be ready in 10 minutes and get hired on-the-spot. That’s how long I took to sign up for a trial account anyway – and I wasn’t even rushing!  After all, you can always switch to an on-site deployment after the new servers arrive.

What are you still waiting for? – Time to check out Office 365 if you’ve not done so yet!

Why Office 365 is Good for Exchange Administrators

Free ebook download: Top 10 Most Popular Troubleshooting Posts for Email Administrators

Autodiscover in Exchange 2010 is one of those critical little black box services that just seems to work, chugging along quietly behind the scenes, making it incredibly easy to connect Outlook, Windows Mobile, and Entourage clients to Exchange. That is, until it doesn’t, and then things just turn ugly very quickly. While older Exchange 2007 implementations could function with an improperly configured Autodiscover, Exchange 2010 organizations depend upon it, especially when clients want to share calendar information externally, and/or integrate with Office Communications Server or Lync Server.

Autodiscover provides information to other Exchange servers within the organization as well, but in this article we are just going to cover the client side of things. To ensure that things go along as smoothly as possible, let’s take a look at what Autodiscover is and what it needs in order to run smoothly.

What is Autodiscover?

Enabling the service is pretty easy, since you get it as soon as you install an Exchange server with the Client Access Server role. A virtual directory under the IIS default site is created called “Autodiscover.” This contains the information needed to configure a client. Supported clients include Outlook 2007 and 2010, Windows Mobile 6.1 and later, Entourage clients, and others. Here is what Autodiscover provides to clients:

• The Client Access Server name(s) that Outlook should use to connect to the user’s mailbox
• The URL for the Offline Address Book
• The URL for free/busy information
• Configuration information for the profile

Authentication

Clients authenticate using the user’s email address and password, or the domain account if the client is a domain joined machine.

DNS

Outlook (and other) clients look for the Autodiscover service using DNS lookups. You want to add an A record for the hostname “autodiscover” in the same DNS namespace as you use for your SMTP addresses, so if your users’ email is in the form username@example.com then you create an A record for autodiscover in the example.com domain. You should use an A record; a CNAME record can work but it will cause the client to present an error to the user. You can also implement an SRV record, though this will also cause the client to present an error. There is a registry hack to prevent this for Windows clients, but it’s better to just use an A record. Autodiscover  can also be located within Active Directory using Service Connection Point Objects.  

Configuring Autodiscover for external access

Clients external to your network may be able to connect to Exchange, but may also have problems with services like the OAB and Free/Busy unless you configure Autodiscover to work with the external access you set up, usually by publishing through TMG. Here are the commands to execute in the EMS to configure external access to work correctly. Run these on your CAS server, named DCCAS01 in this example, where each box is entered as a single continuous line.

Enable-OutlookAnywhere -Server DCCAS01 -ExternalHostname
"mail.example.com" -DefaultAuthenticationMethod "Basic"
-SSLOffloading:$False

Set-OABVirtualDirectory -identity "DCCAS01\OAB
(Default Web Site)" -externalurl
https://mail.example.com/OAB -RequireSSL:$true

Set-WebServicesVirtualDirectory -identity "DCCAS01\EWS
(Default Web Site)" -externalurl

https://mail.example.com/EWS/Exchange.asmx

-BasicAuthentication:$True

Certificates

Of course, connecting clients to Autodiscover needs to be done using SSL, and this requires a certificate. Since you will probably be using smartphones in your organization, you really want to get a certificate from a public CA rather than rolling your own. You can use a wildcard certificate for the domain, but that can be a very expensive certificate to obtain from your public CA. If you review our article on the Exchange Certificate Wizard, you will see how to generate a CSR that includes the Autodiscover Subject Alternate Name.

I hope you found this post useful. In a followup post, we’ll look at setting up Autodiscover for site affinity, which is desirable when you have multiple AD sites, each with a CAS server and you want to keep client traffic local.

Inside Exchange 2010:Exchange Autodiscover

Free ebook download: Top 10 Most Popular Troubleshooting Posts for Email Administrators

After a painstaking examination of the various pros and cons of signing up for a cloud-based email service and that of an on-premise deployment, your company finally decides on the latter option.  Before jumping into deployment phrase however, there remain a number of important decisions that need to be made first.  Today, I want to highlight some of these areas, and offer some suggestions that I hope will be helpful to administrator tasked with setting up Exchange Server.

Deployment Scenario

While this article is about setting up Exchange Server “on-premise,” it is not an altogether uncommon occurrence for companies to host their servers in a data center.  Administrators should decide early if they would like such a deployment scenario, since cost and other practicalities may curtail the number of servers or appliances placed with a hosting provider.

On the other hand, businesses that opt to setup their Exchange Server within the bounds of their corporate networks will have another set of decisions to make.  This includes availability of sufficient upstream and downstream bandwidth on their existing Internet connectivity, and whether there is adequate static IP address for allocation to the new mail server.  In addition, redundancies may also need to be examined in terms of fallback Internet access and presence of uninterruptible power supply (UPS) to guard against power trips.

Edition of Exchange Server

A decision for Exchange 2010 is pretty much a no-brainer for companies setting up Exchange Server for the first time, though some may stick with the older Exchange 2007 for various reasons.  Do note however that both Exchange 2007 and Exchange 2010 require the presence of a 64-bit processor – which means that your 5 year old server hardware may not make the cut.  Finally, depending on whether you have the license for the stand-alone version of Exchange Server or as part of Small Business Server, there might be a need to acquire Microsoft Outlook separately.

And yes, companies who may be unable to deploy Exchange Server, but desire to have something compatible with Outlook may want to read Exchange-compatible email servers for suggestions.

Protective Mechanisms

Protective mechanisms can be segregated into two distinct components: protecting end-users from malware and spam, as well as procedures and tools to defend your Exchange Server from malicious hackers.  I wrote a post on Securing Your Microsoft Exchange 2010 Server in March, which linked to various resources with tips on how to defend your Exchange Server.  Getting a good spam filter is usually a more challenging proposition however, thanks to the constantly changing tactics used by spammers.  On this front, I would recommend that administrators check with sister-site All Spammed Up for the latest tips and developments on the anti-spam front.

Backup and Archiving

Inexperienced IT professions may confuse the need for proper backup and archival with the protective mechanisms mentioned in the previous section – they are not the same thing.  Although reactive in nature, backup and archival measures play a vital role to help businesses recover from catastrophic failures.  Indeed, even the largest corporations in the world like Google make use of offline backup as a last line of defense.  In the case of Google, I chronicled in The Big Gmail Crash and the Lesson for Email Administrators how the company’s tape backups helped them to recover from an internal bug that left the mailboxes of some users corrupted earlier this year.

Decide on an Exchange Server Role

Finally, businesses who are installing Exchange Server 2010 should be aware that it can operate in various roles:

• Mailbox Server
• Client Access Server
• Unified Messaging Server
• Hub Transport Server
• Edge Transport Server

All the above roles can be combined with the exception of Edge Transport server role, which is designed for deployment on perimeter networks.  An Exchange Server configured as an Edge Transport Server allows the establishment of a secure boundary to buffer between the internal network and the Internet – in effect acting like a proxy.

Administrators who are not familiar with the various roles of Exchange 2010 may want to look at Exchange 2010 server roles explained, which offers detailed explanations together with tips about hardware requirements.  In addition, Microsoft’s TechNet Understand the Exchange Server Roles in Exchange Server 2010 is also a worthwhile read on this topic.

Are there any other considerations that I’ve missed out?  Feel free to chip in!

Decisions to Make When Deploying an On-Premise Exchange Server

Free ebook download: Top 10 Most Popular Troubleshooting Posts for Email Administrators

Despite the widespread use of instant messaging and the recent rise in the popularity of social networking tools, there is little doubt that the humble email remains the perennial form of digital communication for businesses today.  Its widespread use does imply the presence of the invariable blooper however, or of carelessly written messages that could come back to haunt you.  I call such situations the “Oops!” moment.

I’ve highlighted some of the most common ones below, and it is my hope that it can led to users exercising more caution before clicking on the “Send” button.  And yes, do feel free to chip in with a comment or two about similar mistakes that you may have witnessed, or have committed yourself.

1. Hacked email accounts

I wrote recently that it is never good news to have any server compromised by hackers or corporate espionage.  Yet few IT managers or administrators would spend time mulling over the repercussions of a hacked Exchange Server account.  As you can imagine, the most obvious consequence here would be the pilfering of critical information email correspondences, which could include trade secrets and other highly confidential data.

Moreover, even non-proprietary information could be a cause for embarrassment, as evidenced when hacker group Anonymous broke into HBGary Federal’s site and made away with 71,000 emails.  Borderline illegal suggestions made by the company’s then chief executive Aaron Barr suddenly became public knowledge when all his emails were posted online, culminating in his eventual resignation.

2. Subpoena or legal discovery

A court subpoena can be issued for anything ranging from criminal cases to civil lawsuits, and is typically used to compel the production of evidence from the accused.  Where it pertains to email messages, this could mean that all the correspondences ever received or sent across a specific time frame could be subjected to detailed analysis by lawyers combing for evidence to support their case.  It is hence important to understand that even simple nuances or voicing of intent could be construed as incriminating evidence or serve to significantly weaken one’s case.  Unlike a hacked account though, details in personally embarrassing emails can usually be counted on to stay under wraps.

3. Sending to the wrong person

I recently received an email from a PR folk that is different from the dozens of the press releases and pitches that I receive on a daily basis.  This came from someone whom I have exchanged correspondence with in the past, and was apparently sent in haste.  Thanks to the “autocomplete” feature in Microsoft Outlook, my name was added given its similarity to one of the recipients who was also named “Paul” – by mistake.  Ironically, when an email revolves around a person, I have found that there is actually an increased likelihood of unconsciously typing the person’s names in the “To:” fields. In addition, my guess is that most people have sent out the wrong file attachments at some point or other in their lives – in fact, I just did it last week.

4. Broadcasting instead of sending to a specific person

A relatively frequent occurrence in some larger corporations would be the presence of employees sending out email messages addressed to the entire company.  Due to the same “autocomplete” features mentioned in the previous section, I have seen my fair share of emails that were obviously intended for an individual, but inadvertently sent to the entire company instead.  Another common mistake would be hitting the “Reply all” button on a company-wide or department-wide email message and proceeding to either craft a private reply, or asking a question not intended for a larger audience.

5. Forgetting to redact before forwarding

Somewhat related to the previous scenario, I have also received emails containing information that were clearly not meant for my eyes.  A common practice in many enterprises, the idea behind forwarding an email chain is to help colleagues or partners to quickly get up to speed without having to revisit the rationale behind a particular decision.  As you can imagine, mistakes involving information that should have been redacted but were not is a scenario that has taken place before.  Further compounding the situation are certain email platforms such as the BlackBerry smartphone in which forwarded emails cannot be edited.

5 Most Common ‘Oops!’ Moments with Email

Free ebook download: Top 10 Most Popular Troubleshooting Posts for Email Administrators

The prevalence of free and high-quality web-based email services has undoubtedly helped advance the prevalence of emails. Indeed, one of the first stops for a new Internet user these days would be to first pick up an email account or two at one of the free webmail providers.  Given the familiarity of users with web-hosted emails, should Exchange Administrators be at all concerned that Exchange Server would eventually lose its appeal?

Well, my personal opinion is that Exchange Server will continue to retain its relevance for some time yet, especially in the realm business. I’ve highlighted some of the reasons below.

1. The Hosted Exchange route

Buoyed by the advantages of a cloud-based deployment, some companies have made a strategic decision to migrate their on-premise server deployments into the cloud.  This doesn’t necessarily sound the death knell for Exchange Server however, given Microsoft’s foresight in creating a version of Exchange for cloud deployment.  Depending on the flexibility of partners and the size of your deployment, Email Administrators can leverage on the full breathe of capabilities found in Exchange but set up as a hosted solution.

2. Web email with Outlook Web Access

Employees or businesses that desiring a Web-only approach to cut down on maintenance costs will still be able to tap into Outlook Web App (OWA).  As implemented in Exchange 2010, OWA lets staffers effectively access their email and voicemail from any of the major web browsers on the market (Internet Explorer, Chrome, Firefox, Safari).  Users are able to access their calendar, contacts and tasks – providing a level of usability from a web platform practically indistinguishable from that of a desktop experience.

3. Convenience of Outlook

I’ve used a variety of email clients over a span of 15 years, ranging from the likes of Eudora in the past, and open source ones such as Thunderbird.  I’ve eventually gone back to Microsoft Outlook 2010, which I currently use on a day-to-day basis.  As I wrote in an article published on TheEmailAdmin last year, Outlook 2010 not only offers a polished interface but includes advanced features for business collaboration such as shared calendars, threaded view, and support for connecting to multiple Exchange Servers.

4. Popularity of Exchange ActiveSync

Confronted with RIM’s robust push mail technology, Microsoft created the very first version of Exchange ActiveSync (EAS) in 2002.  The technology was subsequently enhanced and shipped together with Exchange Server 2003; and the EAS protocol has come a long way since those early days.  For example, Exchange Server 2010 shipped with EAS 14.0 which incorporates the ability to look up the free/busy status of a user as well as SMS syncing, among other new capabilities.  So not only is EAS a cornerstone of Exchange Server today, but the protocol is also widely implemented on other operating systems such as the iOS and Android.

5. Strength of Archival Options

Google’s commitment to achieve zero downtime for Google Apps and the company’s revision of its SLA terms notwithstanding, Gmail suffered an outage earlier this year after a buggy storage driver update resulted in corrupted data being replicated across its data centers. Thankfully, offline tape backups meant that no data were actually lost.  As I highlighted in The Big Gmail Crash and the Lesson for Email Administrators in March, one of the lessons gleaned from the outage pertains to the value of an offline backup.

The crux of the matter has to do with the fact that while it is undeniable that many cloud hosted solutions are highly redundant, users have practically no control over the actual backup or archival process.  This is underscored by various third-party vendors that swiftly unveiled software tools for offline archival of Gmail accounts.  Unfortunately, though these utilities may be highly usable, they are ill-suited for the demands of the average businesses.

In comparison, Microsoft Exchange is a highly-respected messaging server that has been around for more than 15 years.  Deployed by some of the largest enterprises, Exchange support can be found in every business-centric archival and backup application today.  Moreover, there are also many tried-and-tested tools that work exclusively with Exchange to deliver the maximum choice for administrators when it comes to backup and archival capabilities.

While it would be impossible to project the popularity of Exchange Server another 20 years down the road, I think it is safe to say that Microsoft’s flagship messaging server won’t be going away anytime soon.

5 Reasons why Microsoft Exchange Server will Remain Relevant

Free ebook download: Top 10 Most Popular Troubleshooting Posts for Email Administrators

Is your email inbox literally bursting at the seams every time you open it? If it is, then don’t you think that perhaps it’s time to get a little more organized? Having an overflowing email inbox is the main cause of your email client slowing down, and it also means you waste time not being able to find crucial emails in a hurry.

I understand it might seem like a daunting task to get yourself organized, but it’s really not so difficult when you know how. The first step on the road towards organization is cleaning up your inbox, followed by some intelligent archiving of your emails. In this post I’m going to outline my simple Microsoft Outlook system for keeping my emails tidy, and I’ll also throw in some tips on how you can archive your older emails too. And even if you use another email client instead of Outlook, you can probably apply these tips anyway.

The most important tool that Outlook has is the AutoArchive feature. It allows you to do all kinds of things, including directing where archived data should go and specifying how old items need to be before they are archived.

1 – Globally Configuring AutoArchive

Setting up AutoArchive is a very easy process. Go to Tools > Options > Other > AutoArchive, and then choose the settings that work best for you. My personal preference is for a weekly cleanup, and to be informed when it’s about to do so. Another thing I like is to collect all of my archived data into just one archive folder (Archive.pst), and then as the year progresses I will manually move the old data to monthly archives. These are the settings I recommend for easy organization:

• Turn on – AutoArchive every week
• Turn on – AutoArchive prompts
• Turn off – expired item deletion when AutoArchiving
• Set Archive.pst as default archive file

2 – Setting AutoArchive Properties for Individual Folders

If you want to set the properties for your individual folders, do this:

Select the folder > Right Click > Properties > AutoArchive and then choose the settings you want. Don’t forget to repeat this for each folder that you wish to archive.

Recommended settings:

• Turn on – Clean items more than 1 month old
• Turn on – Move old items to default archive folder

3 – Manually Move Archived Files to Monthly Folders

This should be done each month, in order to have a nice organized monthly record of all your emails, just like mine. To do so, you need to create a new folder each month, something like “Archive 2010 December n.pst”.

By doing this, your archived files will be nicely organized when you come to view them all in Windows Explorer or the File Open box. Creating a new PST file is very easy, simply follow these steps:

Select File > Personal Folders File (.pst) > Choose a folder > Enter the name > Click Create. Make sure that the descriptions you use each month are consistent, so that Windows will file them in a nice, organized way. As for the other options, I just leave them all set as default. You should now be able to see the new PST folder listed in your Folder List or Outlook bar, and it will contain only one folder – Deleted Items.

4 – Copy Data Before You Move It

It is strongly recommended that you copy your data before you attempt to move it. Once you have successfully copied the data, you can then delete it from its source. You need to do this because copying or moving files is very resource-consuming, and will slow everything else on your computer down. Should you get the “Low Resources” message flashing up on your screen, there’s a good chance that something will go wrong with the operation and you could lose data. So always make a copy first.

5 – Tidying Up Your Monthly Archives

Once a new month begins and there is no more data for that month coming in, you can tidy everything up before dumping it into your new PST folder for the past month. You may or may not want to take out any old attachments, and you should also check that no records are saved in the Deleted Items folder.

You can open an archival PST file by selecting File > Open > Personal Folders File (.pst) > Choose the file you need > Click OK. Note that you only have to open these archival PST files when you are moving data into them.

When you want to close a PST, simply right click it on your Outlook folder list and select the “Close” option.

6 – Compacting Your PST Files

Doing this will not only leave everything nice and tidy, but it will save a load of space on your hard drive too, so it’s always a good idea. First of all, you need to close any applications you have running, including the Task Scheduler. Now, right click on the PST you wish to condense > click Advanced > Compact Now. This may take a while, even several minutes depending on how big the file is, but whatever you do, do not interrupt the process. Once it’s finished, clear all dialogs and finally close the folder.

7 – Don’t Let Your Archive.pst Get too Big!

You should routinely check your archive.pst folder (before each monthly archive) to make sure it doesn’t get too unmanageable. My personal rule is to compact it when it gets too big, but if it’s over 80MB then you should carry out some manual pruning first, because the compacting operation is somewhat untrustworthy.

7 Tips For Managing Outlook Email Archives

Free ebook download: Top 10 Most Popular Troubleshooting Posts for Email Administrators

Outlook Connector can be a very valuable tool for administrators to implement in their environment. It is used to facilitate the connectivity to email accounts outside of Outlook such as: Live Hotmail, Gmail, Yahoo! and AOL.

In his blog, “The Outlook Connector”, Kent C. briefly describes some of the functionality that Outlook Connector has. He describes how Outlook Connector can be used to access outside email accounts, calendars and contacts. It provides the capability to reply to emails using an end-users personal email address rather than the corporate email address. Administrators should ensure that this feature is available to their company employees, not to encourage access to personal emails on company time but to enable a company’s employees to respond to outside emails using their personal email addresses. Using this method, an employee can keep their personal business activities separate from their work-related business activities.

The Outlook Connector uses technology called DeltaSync to synchronize outside email, calendar and contact information. Administrators should be aware that Microsoft would like the DeltaSync communications protocol to be the protocol of choice when it comes to synchronizing contacts, calendar and notes. DeltaSync is favored by Microsoft over traditional protocols such as POP4 or IMAP4. It is Microsoft’s vision that various devices would use the DeltaSync protocol as a common synchronization technology for web services such as: email, contacts, calendar and notes. Offline clients are able to get access to their email using DeltaSync and Outlook Connector.

Another capability that can help company employees to be more efficient is the Outlook side by side calendar support.

Using this feature an employee could drag an appointment from their work calendar on one side to their Hotmail Calendar on the other side. Oftentimes employees might get a call at home while they are away from their office computer so they enter an appointment on their home calendar. Later they are able to synchronize their personal calendar with their work calendar. This allows employees calendars to always be in sync so that they never miss an appointment or an important meeting. This is one of the reasons why email administrators should implement Outlook Connectors in their work environment so as to encourage productivity and to ensure a fluid transfer of work from home to office and vice-versa.

But there are a lot of questions and concerns that can occur when using Outlook Connector that email administrators should be knowledgeable about before implementing it.

1. Why does Send/Receive have to be clicked in Outlook 2003 in order for the Outlook Connector to synchronize?
   The answer is that Outlook 2003 does not send and receive email messages automatically like Outlook 2007 does. Administrators should notify their end users that they need to click Send/Receive in order to force synchronization when using Outlook 2003 as their client. Administrators should consider offering a mechanism, to their end users, to schedule an automatic send/receive operation. This will ensure that email, calendar events, notes and contacts are always up to date. If an administrator wishes to schedule automatic send/receive operations then they can select the Send/Receive option from the Tools menu, choose the  Send/Receive Settings, and then click on Define Send/Receive Groups.
2. How do I migrate “My Calendar” data that is stored in a MSN Premium account to the Windows Live Calendar?
   An administrator will have to install the Outlook Live Connector (OLC) 12.1 on the same machine that is currently using OLC 12.0 or 12.1. Next, make a connection to the Premium account. Your data will automatically be migrated to Windows Live Calendar by Outlook Live Connector.
3. What is needed to make the connection?
   There are three requirements for a Windows Live Hotmail connection to work: an Internet link, an installed copy of Outlook and all accounts must be updated to the new Windows Live Hotmail. The Microsoft website has information about how to update your accounts. Outlook may need to be restarted in order for the Connector to work.
4. Sometimes attachments are not downloaded when Outlook Connector is used. Why?
   This is a known issue with some proxy servers and usually occurs in corporate environments. The proxy servers prevent Outlook Connector from downloading email items that contain attachments. Administrators should inform their end users that attachments can still be downloaded and viewed from Windows Live Hotmail or from Office Live Mail.

These are just a small snapshot of some issues and concerns that an administrator may encounter when implementing Outlook Connector in their corporate environment.  Admittedly, Outlook Connector may add some administrative overhead so the costs/benefits should be looked as per each company’s email best practices and policies.

Explaining Outlook Connector Issues and Concerns

Free ebook download: Top 10 Most Popular Troubleshooting Posts for Email Administrators