Troubleshooting Emailing via MS Outlook
AutoMailMerge and AutoDocMail plug-ins for Adobe® Acrobat®
List of Common Emailing Issues
- Use "Classic" MS Outlook
- Turn Protected Mode Off
- Test Email is not Received
- Outlook Asks for Permissions Before Sending Each Email
- Errors or Application Crash while Sending a Test Email
- No Emails Sent via Microsoft 365 (No Error Returned)
- Some Emails are failed to Send
- Some Emails are not Received
- Unable to Send Emails from a Shared Mailbox
Use "Classic MS Outlook
Make sure you are using "Classic" Microsoft Outlook app, not a "new" Outlook that does not provide functionality for sending emails via locally installed MS Outlook application.
Turn Protected Mode Off
Make sure Adobe Acrobat is not running in Protected Mode. It is not possible to use the software while Protected Mode is enabled. Protected Mode blocks all non-PDF file access. Please see the following page for instructions on how to disable Protected Mode in Adobe Acrobat.
Test Email is not Received
If a test email is sent successfully, but it is not received and does not appear in Sent folder in Outlook, then the first step is to repair Microsoft Outlook. Please see the following support page on Microsoft web site with instructions on repairing MS Office application.
If repair does not help, then try creating a new Outlook profile (without deleting an existing one) and use a new profile to send emails. Here is a link to Microsoft support page that explains how to create a new profile.
Outlook Asks for Permissions Before Sending Each Email
If Outlook does not detect a valid or up-to-date antivirus, it will assume a higher risk environment and may issue prompts before sending emails. Make sure anti-virus is installed and enabled.
Another reason might be Outlook’s Trust Center settings may be configured to prompt for permission before allowing access to sensitive actions, such as sending emails or accessing your address book. You can adjust these settings under: File > Options > Trust Center > Trust Center Settings > Programmatic Access menu in MS Outlook.
Select File > Options from Outlook menu and select Trust Center category. Next, press Trust Center Settings button.
Select Programmatic Access category. Verify anti-virus status (should appear as Valid) and Send email messages on your behalf option is listed.
Errors or Application Crash while Sending a Test Email
Make sure you are not running Adobe Acrobat in Protected Mode. It is not possible to use the software while Protected Mode is enabled. Please see the following page for instructions on how to disable Protected Mode.
If you are unable to send a test email (Protected Mode is off) and do not receive any error messages, then please check application permissions and anti-virus settings to make sure Adobe Acrobat is allowed to execute the following two Powershell scripts:
AutoMailMerge (64-bit Adobe Acrobat DC):
C:\Program Files\Adobe\Acrobat DC\Acrobat\plug_ins\AutoMailMerge\sendxml.ps1
C:\Program Files\Adobe\Acrobat DC\Acrobat\plug_ins\AutoMailMerge\send_email.ps1
AutoDocMail (64-bit Adobe Acrobat DC):
C:\Program Files\Adobe\Acrobat DC\Acrobat\plug_ins\AutoDocMail\sendxml.ps1
C:\Program Files\Adobe\Acrobat DC\Acrobat\plug_ins\AutoDocMail\send_email.ps1
Some Emails are Failed to Send
If, after sending a batch of emails via a locally installed Microsoft Outlook (via Extended MAPI), some messages fail to send — typically those addressed to recipients from a specific domain (for example, @yahoo) — and the error "Error adding a mail-to recipient" is returned, this usually indicates a problem with the user’s address book configuration or Outlook profile.
The first step is clear AutoComplete cache. In Microsoft Outlook, select File → Options from the menu. Choose Mail category, scroll down to Send Messages section and press Empty Auto-Complete List button:
If the issue persists, create a new profile in Microsoft Outlook for the affected user and reconfigure the mailbox. Then repeat the test using the new profile.
Some Emails are not Received
If after sending files some recipients (but not all of them) report that they did not receive emails and emails addressed to them do not appear in the Sent folder (in MS Outlook), then please check if recipients that did not receive emails are listed in the contact list for the email account used for emailing. If this is the case, try reparing MS Outlook first. If repair does not help to clear the issue, then try removing these emails from the contact list (and add them back later) and check if this fixes the problem.
No Emails Sent via Microsoft 365 (No Error Returned)
If emails are not being sent through Microsoft 365 when triggered programmatically (e.g., via "silently via Microsoft Outlook" method), and no error is reported, check the following:
Check Restricted Users and Anti-spam Policy:
- Go to Microsoft 365 Defender online (https://security.microsoft.com) and login into your account.
- Navigate to: Email & collaboration > Review > Restricted entities.
- Verify whether the affected account is listed. If the user appears here, outbound email sending may be blocked
- Check anti-spam policy: navigate to Email & collaboration > Policies & rules > Threat policies > Anti-spam.
- Open the Outbound anti-spam policy and look for: users restricted from sending email, any indicators that the user has been flagged, sending limits or enforcement actions.
Check Message Trace:
- Login into the Exchange Admin Center (https://admin.exchange.microsoft.com).
- Go to: Mail flow > Message trace.
- Review messages sent externally and check for Status = Blocked or Status = Failed with spam-related reason.
If there is nothing listed in the message trace, then it maybe a local issue. In this case, try to create a new Outlook profile on the local computer, re-add the mailbox and test with a new profile.
Unable to Send Emails from a Shared Mailbox
If you are unable to send emails from a shared mailbox email address, then create a new Outlook profile with just the shared mailbox email account and use this profile to send emails.
Email-to-PDF Conversion