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Outlook 2016 Attachment issue RRS feed

  • Question

  • We have deployed Outlook 2016 to 2 machines in a client environment and both are now having issues sending attachments. Both machines are Windows 7 Pro and mail server is Exchange 2010. 

    Machine A ) Will always send 1 less attachment than intended. So if I attach 3 files 2 will send, if I send 4 files 3 will send. In Outlook all attempted files to send appear in sent items

    Machine B ) Will send only 1 attachment. If I attach 4 files only 1 will send, if I attach 3 files only 1 will send. In Outlook all attempted files to send appear in Sent Items.

    Troubleshooting Attempted:

    -Tried reinstalling office

    -Upgraded office to newest release

    -Disabled all anti-virus/security software

    -Disabled all Outlook add-ins

    -Logged in as a different user and configured a different mail profile, same issue

    -Confirmed issue was with every file type not just a specific type of file

    -Outlook Web Access works without issue as does older versions of Office

    I went through the following discussion without finding any answer:

    http://answers.microsoft.com/en-us/msoffice/forum/msoffice_outlook-mso_win10/office-2016-attachment-bug/a20a346d-2875-4516-8ab1-0ed83faed24a?page=1

    Let me know if any more information is needed. Any help would be appreciated.

    John

    Friday, September 16, 2016 4:10 PM

Answers

  • I was able to resolve this issue on my own. 

    To clarify the issue for anyone that comes across this again:

    -Any users using Outlook 2016 were having attachments stripped out of emails

    Resolution:

    We were using CodeTwo on our Exchange server for email signatures and this was apparently having conflicts with Outlook 2016 only. Once I disabled this TransportRule everything worked immediately after

    Tuesday, September 27, 2016 8:47 PM

All replies

  • Hi,

    According to your description, I understand users on the machines can send emails with attachments in OWA.

    And the same issue happened when other normal user logged in the problematic machines.

    If I misunderstood your meaning, please feel free to correct me.

    About your issue, please take the following steps to troubleshoot:

    1. Try to run outlook with online mode for test.

    2. Send emails with attachments to yourself and check the results.

    3.Use Office Configuration Analyzer Tool to check Office program configuration.

    https://support.microsoft.com/en-us/kb/2812744

    Regards,

    David 



    Please remember to mark the replies as an answers if they help and unmark them if they provide no help.
    If you have feedback for TechNet Subscriber Support, contact tnmff@microsoft.com.

    Monday, September 19, 2016 9:47 AM
  • Hi David,

    I have tried changing the Outlook profile to online mode and have the same problem.

    I ran the diagnostic tool and it didn't show any relevant errors, a couple warnings about the OAB but that's it.

    Please let me know if you have any other suggestions.

    John

    Wednesday, September 21, 2016 6:09 PM
  • Hi,

    Sorry for delay.

    I will ask some related questions for better analysis.

    1. I notice that all attempted files to send appear in sent items, whether the recipients can view all the attachments?

    2. Does the issue occur on two specific computer? Have you tried to use outlook in other computer?

    3. Did you change any outlook settings?

    To narrow down the issue, I suggest we try to install outlook on a brand new machine then send emails with attachments to test.

    On outlook side, please try to change the message format to Rich Text or plain text then check if the same thing happens.

    Regards,


    David Wang
    TechNet Community Support


    Please remember to mark the replies as an answers if they help and unmark them if they provide no help.
    If you have feedback for TechNet Subscriber Support, contact tnmff@microsoft.com.

    Tuesday, September 27, 2016 7:17 AM
  • I was able to resolve this issue on my own. 

    To clarify the issue for anyone that comes across this again:

    -Any users using Outlook 2016 were having attachments stripped out of emails

    Resolution:

    We were using CodeTwo on our Exchange server for email signatures and this was apparently having conflicts with Outlook 2016 only. Once I disabled this TransportRule everything worked immediately after

    Tuesday, September 27, 2016 8:47 PM
  • John, can you reply back stating what you did after disabling CodeTwo? I am having the exact issue.
    Tuesday, August 8, 2017 9:13 PM
  • We have found this is due to the signatures themselves. If a user has a poorly coded signature with embedded images (e.g. if they've created it in Outlook), then we experience weird behaviour with attachments.

    Try removing the images from your signature as a test. To resolve, I've had to code the email signatures manually.

    Thursday, January 11, 2018 10:48 PM
  • The removing of the signature fix my end user's issue with sending attachments. Do you know type of embedded images cause the issue? We have many with similar image on their email signatures.
    Wednesday, April 4, 2018 7:10 PM