How to Fix: Cannot Attach Files to Reply in Outlook 2016
Infopackets Reader Steven B. writes:
" Dear Dennis,
I have a small issue, and hope you have some insight. I am using Outlook 2016; when I respond to an email, I can no longer attach a file to my email reply. This seems to have happened all the sudden, whereas previously it worked without any problems. I have tried to drag and drop a file into the email, and have also clicked on the Attach File icon (paper clip) button without any luck. The strange thing is that this issue only affects my email replies - but not when I compose a new email.
I have searched online the Internet but can't find anything. Based on some online explanations, I have tried: rebooting the PC, pressing the ESC button multiple times, and also ensuring that Outlook 2016 is not started in Administrator mode. None of these worked. Any ideas? "
Although this is somewhat not related: an old trick I learned in the past with Outlook Express is that if you forward the email (instead of replying to it), you can extract attachments.
Not being able to access email attachments was a security measure developed by Microsoft, but forwarding the email would allow you to access the attachments. I realize this is not what Stephen was asking, but thought perhaps it might be another way he could manipulate Outlook 2016 so that he could add attachments to his replies (by forwarding them instead).
I sent Stephen that explanation and he replied:
" Just an update. I solved the problem; well, discovered a workaround, but something far more sinister is going on here. It seems - for no reason that I can think of - you can no longer attach files to (some, but not all) plain text emails in Outlook 2016.
However, clicking on the Format Text menu item, then selecting HTML fixed the problem. After further examination, it appears that the troublesome emails that were not allowing me to add attachments were in fact 'Plain Text' emails. "
Thanks for the update Stephen and I hope that this helps others with a similar issue.
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About the author: Dennis Faas is the owner and operator of Infopackets.com. With over 30 years of computing experience, Dennis' areas of expertise are a broad range and include PC hardware, Microsoft Windows, Linux, network administration, and virtualization. Dennis holds a Bachelors degree in Computer Science (1999) and has authored 6 books on the topics of MS Windows and PC Security. If you like the advice you received on this page, please up-vote / Like this page and share it with friends. For technical support inquiries, Dennis can be reached via Live chat online this site using the Zopim Chat service (currently located at the bottom left of the screen); optionally, you can contact Dennis through the website contact form.
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