Relevant Product: Signature Manager Exchange Edition
WARNING! The following products were discontinued on 30 September 2022:
- Exclaimer Signature Manager Outlook Edition
- Exclaimer Signature Manager Exchange Edition
The end of Support for these products is 30th September 2024.
For more information, please see the Discontinued Questions and Answers page.
Scenario
When you update the Sent items, you receive a warning message in the Exclaimer Event log (click the Status link on the right-hand side of the product console to open the event log).
This article describes how you can troubleshoot the common problems that can occur when the Sent Items Update is enabled.
The most common problems are listed below:
There was an error updating Sent Item for the sender
Request failed. The underlying connection was closed: Could not establish trust relationship for the SSL/TLS secure channel.
There was an error updating Sent Item for the sender
Unable to locate message with subject sent on message date and time.
An invalid Exchange Web Services and/or Autodiscover SSL certificate was identified while updating the Sent Items for user senders email address. Further errors were suppressed for the specified user for 2 hours.
There was an error updating Sent Item for the sender
The operation cannot be performed because the item is out of date. Reload the item and try again.
There was an error updating Sent Item for the sender
Request failed. The remote server returned an error: (401) Unauthorised.
There was an error updating Sent Item for sender
Request failed. The remote server returned an error: (507) Insufficient storage.
Microsoft.Exchange.WebServices.Data.ServiceRequestException: The request failed. The remote server returned an error: (401) Unauthorized. ---> System.Net.WebException: The remote server returned an error: (401) Unauthorized.
Resolution for:
Status: Warning
There was an error updating Sent Item for the sender
Request failed. The underlying connection was closed: Could not establish trust relationship for the SSL/TLS secure channel.
This error occurs due to the time zone, date and time.
Using the Autodiscover service, Sent Items Update relies on being able to locate the message in the mailbox store by matching the message date, time and subject. If any of these are incorrect or out of date then the Sent Items Update will be unable to locate the message for updating and will fail with a warning after five minutes.
- Make sure that the date and time, including the Daylight Saving settings, are configured the same between the server and client.
- When you make changes to the Daylight Saving settings you need to reboot the computer for the changes to take effect.
- In some cases, although the Daylight Saving has been enabled, the status still shows that the clock is not set to adjust for this change. In this case, disable then re-enable the Daylight Saving setting to correct this behaviour.
Resolution for:
Status: Warning
There was an error updating Sent Item for the sender
Unable to locate message with subject sent on message date and time.
This error occurs when the Sent Items Update is not able to locate a message if it has not yet been synchronized to the mailbox on the server, from the Outlook OST file on the local machine.
- Make sure that Cached Exchange Mode is not the cause of the issue. Disable this feature in Outlook to cross-check if it is affecting it.
You will be required to close and re-open Outlook for this change to take effect.
Caution: It's not possible to configure how frequently Outlook will synchronize the OST file to the mailbox. This is dependent on availability and how busy the environment is. - If removing Outlook from cached mode does not resolve the issue, then try reducing the size of the Sent Items folder in the problem user’s mailbox.
If the folder contains a large number of items, try moving them to a new folder. This may allow Microsoft Outlook to synchronize quicker.
- If the messages sent from Microsoft Outlook are still not updating, identify if the problem occurs when you send a test email from the Outlook Web App (OWA).
Make sure that when you log on to the OWA - the time zone specified is the same as the server.
To check the OWA Regional Settings:
- Log in to OWA
- Click Options then click See All Options
- Click Settings then click Regional
Warning:
Messages that are sent using the Send-As permission will not be updated by the Sent Items Update.
By design, the Sent Items Update searches for the message in the user's mailbox that is being 'Sent-As'. If the Sent Items Update was to search all mailboxes in an environment then this can take a very long time and lead to performance issues, backlogs and so on.
This also applies to messages sent from network appliances (scanners/copiers) that send messages but don’t have an associated mailbox for sent items.
Certain versions of the Exchange will allow you to save the sent items to both the sending user's mailbox and the mailbox for which the email has been 'Sent-As'. For more information, see How to update a sent item which was sent as another user.
Resolution for:
Status: Started
An invalid Exchange Web Services and/or Autodiscover SSL certificate was identified while updating the Sent Items for user senders email address. Further errors were suppressed for the specified user for 2 hours.
This error occurs if the Autodiscover URL is not valid and not working.
In some environments, the Signature Manager Exchange Edition will not be able to determine the correct Autodiscover service URL because Autodiscover may not be working or may be configured incorrectly.
Follow the steps below to obtain the Autodiscover service URL manually and to confirm if Autodiscover is working in the environment.
You can test Autodiscover and obtain the Exchange URL via the Exchange Management Shell.
- Open the Exchange Management Shell and as required, run the following command to test Autodiscover:
For Exchange 2010 or earlier:
Test-OutlookWebServices –Identity <email address>|fl
For Exchange 2013 or later:
Test-OutlookWebServices –Identity <email address> -MailBoxCredential Get-Credential
For, <email address> enter a valid email address of the ExclaimerSIUS account being used in the environment.
- The test results will be shown at the end:
- In the Test-OutlookWebServices results, the output will show the AutoDiscover URL that was being tested.
Copy and paste this into the Exchange URL field on the Sent Items Update settings tab and attempt to update the sent items.
- If the test failed, Sent Items Update may still be able to update sent items if the correct Autodiscover URL is specified manually.
Note: For more information on how to manually configure the Sent Items Update service, see SSL or Autodiscover errors when using the Sent Items Update service in Signature Manager Exchange Edition.
If the Signature Manager Exchange Edition still fails to update the sent items then it may be the case that Autodiscover has not been configured successfully in the environment or is broken.
To test this further, enter the Exchange URL into a web browser and try to authenticate using the ExclaimerSIUS account.
Resolution for:
There was an error updating Sent Item for the sender
The operation cannot be performed because the item is out of date. Reload the item and try again.
This error occurs due to Sent Items Update permissions.
In some cases, the Sent Item configuration wizard is not able to set the required permissions on the Sent Items Update user account.
Resolution for:
Status: Warning
There was an error updating Sent Item for the sender
Request failed. The remote server returned an error: (401) Unauthorised.
This error occurs due to system requirements.
Ensure that the Signature Manager Exchange Edition is installed on a Hub Transport server that meets the system requirements. Although the Signature Manager Exchange Edition will install with Microsoft .NET Framework 2.0; but to make use of the Sent Items Update, you will also need to install Microsoft.NET Framework 3.5.
Resolution for:
Status: Warning
There was an error updating Sent Item for sender
Request failed. The remote server returned an error: (507) Insufficient storage.
This error occurs due to incorrect service credentials.
Ensure that the Exclaimer Sent Items Update Service has been configured to log in with the credentials of the service account that were specified during the configuration wizard and that the Local System account is not being used.
If the service is configured correctly and started, then the Maximum Message Size may need to be increased in the web.config file, on the Microsoft Exchange Client Access Server.
By default, the Maximum Message Size is 35000KB.
To increase the Maximum Message Size:
- On the Client Access server, navigate to \Program Files\Microsoft\Exchange Server\ClientAccess\exchweb\ews\
- Make a backup copy of the web.config file.
- Open the web.config file using Notepad.
- Locate this line on the web.config file:
<httpRuntime maxRequestLength="35000" /> - Increase the value of the httpRuntime maxRequestLength; specify the size in Kilobyte (KB).
- Save the changes and re-test.
Resolution for:
Status: Warning
Microsoft.Exchange.WebServices.Data.ServiceRequestException: The request failed. The remote server returned an error: (401) Unauthorized. ---> System.Net.WebException: The remote server returned an error: (401) Unauthorized.
For a detailed resolution, please see CVE-2018-8581 and how Microsoft's workaround affects Exclaimer on-premises products.