Outlook 2010 with 365 stripping attachments off of email that have been drag and dropped

In my office we just switched to 365 and since this I've noticed that roughly 1/3 to 1/2 of my email with drag and drop attachments are having those attachments stripped off.
Several times a day I send an email that has 6 attachments, mix of excel and pdf, and the excel called 'Checklist' I attach by drag and drop often get stripped off the instant I hit the Send button.
I will literally be looking at it, as one of 6 files, hit Send, and in my sent box there are only 5 files, the Checklist is gone! It's random; about 1/3 to 1/2 of them do this. Others make it through.
Please let me know if there is a fix to this? I'm having to resend attachments about 6 times a day now!

Hi,
Please send several test emails with attachments on OWA, check if this issue will occur.
If the issue is on client only, we can start Outlook in Safe Mode to test, this can eliminate the influence by 3rd-party add-ins:
Press Win + R, type "outlook.exe /safe" in the blank box, press Enter.
In Outlook Safe Mode, send several test emails with attachments to see if the problem will ever occur. If no, we may suspect the issue was caused by some add-ins, go to FILE -> Options -> Add-Ins to disable the suspicious add-ins to verify which one
caused the problem.
We can also test with a new profile to setup the account, a new profile will be a new environment for the account, we can check if the problem will occur with the new profile and you don't need to remove the old profile.
To create a new profile, go to Control Panel -> Mail -> Show Profiles -> Add.
Regards,
Melon Chen
TechNet Community Support
It's recommended to download and install
Configuration Analyzer Tool (OffCAT), which is developed by Microsoft Support teams. Once the tool is installed, you can run it at any time to scan for hundreds of known issues in Office
programs.

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