Title: Outlook 365 (2016) does not send all attachments, only one attachments gets sent
Tags: email;microsoft-outlook;office365;exchange-2010
Question: I have a user who updated to the newest build of Office 365 Build 8431.2242 Click-to-Run. This build (frankly, anything after Build (934)568-8548) is having issues sending more than 1 attachment.
We are using Exchange 2010 SP3 Rollup 20 and reviewing the configuration, there are no attachment limitations that would affect emails in this way.
This issue is not present in the previous Build 6965.2117, in this Build attachments send just fine.
The issue doesn't seem to be on the server side as OWA works fine as well.
I have tried installing the 32-Bit and 64-Bit versions and both do
the same.
I did try using IMAP and that actually worked just fine but if
multiple users are going to upgrade, it would be really inconvenient
migrating everyone to IMAP from Exchange.
I removed Add-Ins
I removed/disabled the Anti-Virus
Recreated the Outlook Profile
Tried in Safe Mode
Contacted Microsoft support but they only did typical troubleshooting like reinstalling Office and running the Fix-It tool. Steps that i already took...
This issue has been going on for 2 years now and build after build this issue has not gone away. I do not know what else i could possibly try but the only "fix" that i get from Microsoft and other forums is to roll back to the previous build (which is my users are running) but i don't think it is very good to be running on such an old version of office.
Any ideas why I'm having attachment issues past Office Build (934)568-8548?
Comment: Hmm. Not sure. I have my own exchange account that I can try to setup and make a random Outlook account just for testing.

Comment: Does this issue occur to other Exchange accounts such as an outlook.com account?

Here is the accepted answer: We have decided to just go ahead and upgrade/migrate to Exchange 2016. Nothing seems to be working.


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