Identifying Exchange Server synchronization issues for Sent Items

Users that access email on various devices may run into Exchange Server synchronization issues. The Sent Items folder is one area that can cause confusion.

Every day more users rely on various devices to access Exchange Server email. I, for example, access my own Exchange email via a desktop computer with Outlook 2010, a laptop (also Outlook 2010), my Windows Phone 7 device, and occasionally Outlook Web App. With the continued proliferation of devices, it's only natural that Exchange Server synchronization issues crop up. One of the most prevalent happens in the Sent Items folder.

I've often noticed that when I send a message from one device, it doesn't always show up in the Sent Items folder on my other devices. This got me wondering why. As I researched the problem, I found that there several different issues that can cause this.

Synchronizing Exchange mail: How are you connecting?

The manner in which a user connects to Exchange Server can often cause synchronization issues in the Sent Items folder. The majority of the time, Exchange Server connectivity is established through a native client, such as Microsoft Outlook 2010 or ActiveSync. That said, Exchange may also be configured to act as a POP3 or IMAP server. This is usually only done if the Exchange administrator needs to provide connectivity to non-Exchange-aware clients.

POP3 is an old protocol and was never designed for Sent Item synchronization. Therefore, if a user connects to Exchange using POP3 and sends a message, the device's Sent Items folder -- if it has one -- will not properly synchronize with Exchange Server.

Any items sent from other devices will still exist within the user's Sent Items folder on the Exchange server, but the contents of that folder will not be replicated to the device connecting to Exchange through POP3.

Mobile device and Exchange synchronization problems

Mobile devices can also lead to a number of different issues in regards to Sent Items synchronization. Although Exchange ActiveSync is a Microsoft technology that natively exists on most mobile devices, not every vendor implements ActiveSync the same way. Some mobile devices require Sent Item synchronization to be manually enabled, other have an option to manually disable Sent Item synchronization.

For example, Windows Mobile 6 has an option that must be enabled if you want to retain Sent Items. To access the option, a user must open the Messaging app and click on Menu -> Tools -> Options -> Messaging. The Messaging tab contains a check box labeled Keep Copies of Sent Items in Sent Folder.

Mobile devices may also temporarily fall out of sync, thereby providing the illusion that a synchronization problem has occurred. Suppose, for example, that a user enters a roaming area and that an implemented ActiveSync mailbox policy prevents him from synchronizing data while he is roaming.

When the user reenters the service area, other folders will synchronize before the Sent Items folder. Even when the Sent Items folder does synchronize, the newest items will synchronize first. Therefore, the user might see his most recently sent items, but may not see items that had been previously sent. Eventually all of content in the Sent Items folder should synchronize.

Exchange synchronization issue: Conversation View

A final issue isn't actually an issue at all, but is often perceived as one. This problem occurs when a user turns on Conversation View, either on purpose or by accident. Turning Conversation View on doesn't stop sent items from synchronizing, but it can cause the illusion of a synchronization failure.

For example, imagine that a user sends a message to a co-worker and Conversation View is accidentally turned on. At some point, the co-worker responds. When the user sends his reply to the message, the original message and the co-worker's response are arranged beneath the most recent message as a conversation and are not logged in the Sent Items folder.

If the user wants to look at the message he originally sent and opens the Sent Items folder to find it, it won't be there. The original message still exists, it just exists within the conversation beneath the most recent message.

About the author:
Brien Posey is an eight-time Microsoft MVP with two decades of IT experience. Before becoming a freelance technical writer, Brien worked as a chief information officer at a national chain of hospitals and health care facilities. He has also served as a network administrator for some of the nation's largest insurance companies and for the Department of Defense at Fort Knox.

This was first published in November 2012

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