Emails in the Sent Items folder are not updated with signatures

Problem:

Some or all messages in the Sent Items folder in the desktop version of Outlook are not updated to display signatures, even though the Sent Items Update feature is enabled.

Solution:

First, make sure that the problem is limited to the desktop version of Outlook. To do that, ask the affected users to sign in to Outlook on the web (OWA) and check if items in their Sent Items folders are updated with signatures. Additionally, ask users to perform the OWA-Exchange-Outlook synchronization test by manually modifying a few messages in their Sent Items folder in OWA, e.g. by adding a flag, assigning a color category, or changing the message status to read/unread. Check if these changes are propagated (synchronized) from OWA to the desktop version of Outlook. Investigate if similar updates synchronize in the opposite direction (from desktop Outlook to OWA).

The solution depends on the outcome of the above actions. Click the links below to learn more.

• Sent items are not updated in both OWA and Outlook
• Sent items are updated in OWA, but not updated in Outlook
• Sent items are not updated in Outlook on the web

Sent items are not updated in both OWA and Outlook

If messages are not updated with signatures in both desktop Outlook's and OWA's Sent Items folder, the problem is most likely related to the configuration of the CodeTwo Sent Items Update service. In that case, double-check your SIU configuration. Detailed instructions are available in the manual for your software:

• CodeTwo Exchange Rules family
• CodeTwo Exchange Rules Pro
• CodeTwo Email Signatures 365

If the information in the manual is not sufficient, check our Knowledge Base articles on SIU troubleshooting or contact our Customer Support for assistance.

Using Open another mailbox in Outlook on the web (OWA)

If you use the Open another mailbox option (Fig. 1.) in Outlook on the web (OWA) to access another mailbox and send an email on behalf of it, Exchange Online won’t copy that email to your mailbox, preventing the SIU service from updating the email with an email signature. As a result, the email without the signature will be listed in the Sent Items folder in both OWA and Outlook.

Fig. 1. Accessing another mailbox in OWA.

Sent items are updated in OWA, but not updated in Outlook

If updates to Sent Items are visible in OWA but not in Outlook, this means that our service works fine and updates your messages correctly. Your problem is most probably connected with data synchronization between Outlook and Exchange Server/Exchange Online. Some users report that their Outlook does not display changes made to emails in the Sent Items folder if these changes (e.g. assigning a flag/category, changing the status) are applied server-side, i.e. in Exchange Server or Exchange Online (OWA). This happens only when Outlook runs in the Cached Exchange mode, regardless of the Outlook version. The problem occurs in various environments.

To solve this problem, you can:

• turn on Online View for the Sent Items folder,
• clear items cached in your Sent Items folder (recommended),
• or disable Cached Exchange Mode.

Turning on Online View for the Sent Items folder

If you do not see signatures in the messages stored in the Sent Items folder, you can turn on Online View for this folder. This will make Outlook display emails directly from your Exchange server, so you should see your emails with signatures.

To turn on Online View locally for the Sent Items folder, select your Sent Items folder from the left menu in Outlook. Then go to the Folder tab and click the View on Server button on the ribbon (Fig. 2.).

Fig. 2. Turning on Online View for Sent Items.

You should now see that your sent emails look the same as sent emails in OWA, with signatures/disclaimers and all other updates visible. Note that enabling Online View does not update your Outlook cache - the program connects to your Exchange server every time you use the View on Server button.

To turn on Online View globally for your users as an admin, you can use one of the available GPO templates. To access the template, sign in to your Exchange server, open Local Group Policy Editor, go to User Configuration > Administrative Templates > Microsoft Outlook 201X (depending on the Outlook version) > Account Settings > Exchange > Cached Exchange Mode, and double-click Use Cached Exchange Mode for new and existing Outlook profiles (Fig. 3.).

Fig. 3. Accessing the GPO template.

Next, choose Disabled and click OK to save your changes (Fig. 4.).

Fig. 4. Enabling the GPO policy, you centrally turn Online Mode on for your users.

Once your users re-run or restart their Outlooks, all the items (sent ones included) will start being displayed directly from your Exchange server (as if the View on Server button was clicked). In other words, your users will now see their sent emails the same way as sent emails in OWA, with signatures/disclaimers and all other updates visible.

Note that enabling Online View will not update your users’ Outlook cache.

Removing items cached in the Sent Items folder

This is the recommended workaround. Follow the steps below to clear all cached mail from your Sent Items folder and update the sent messages with signatures.

1. Right-click your Sent Items folder in Outlook and select Properties from the shortcut menu.
2. Click Clear Offline Items (Fig. 7.).
3. Wait around a minute, so that your Outlook synchronizes with Exchange and downloads the sent items again.

Fig. 7. Clearing cached items in Outlook.

After the refresh, your emails in the Sent Items folder should be updated to display signatures added by the CodeTwo software.

Disabling Cached Exchange Mode

Switching from Cached Exchange Mode to Online Mode in Outlook solves the problem, but it will affect the performance of your Outlook. Read this MS article for more information about the two modes. To learn how to enable/disable Cached Exchange Mode, see this article.

Sent items are not updated in Outlook on the web

If signatures in Sent Items are not displayed correctly in Outlook on the web, you might need to refresh the page in your web browser or open the message in a new window. See this Knowledge Base article to learn more.