How to Fix: Cannot Attach Files to Reply in Outlook 2016

Dennis Faas's picture

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? "

My response:

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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abdulhamidmalik34_5916's picture

It has a "Insert" tag in Task bar having drop-downs Attach a file; Picture-Inline; Share from onedrive.

RButts_5424's picture

The same holds true for Outlook 2013. In fact, "Attach File" menu may not be available until "HTML" is selected.

MarkMessinger's picture

I believe the problem is not so much that you cannot add attachments to plain text email - you can. The problem is, once you've attached the item to a plain text message, Outlook doesn't display any cues there's an attachment there.

So, the workaround is to compose your message as normal. When it's time to attach something, change the message format to either HTML or RTF. Attach the file, as normal. Change the message format back to plain text. Don't worry; the attachment looks as though it disappears. But, if you send the message, the item will be attached, as normal.

I sure hope MSOFT deals with this bug, soon.

iKon's picture

Hi Mark,

Yep looks like this is the case. I have a client with the same issue, when trying to ad a PDF to an email, they cannot see that the file has been attached to the email until formatting the text to HTML.

The problem is, they use a third party program to create their PDF files, then through this third party program add the file to a new email. Natrually when the third party program creates the email, it is created in plain text.

Its not the end of the world, but it is a pain for the customer to have to change this every time. The funny thing is, they reckon this only started happening a few weeks ago, but have been using 2016 for months.

Any help would be greatly appreciated!


AWP8493's picture

Just an FYI - All of a sudden my Outlook stopped letting me insert documents - no matter what format - to my emails. I tried the Microsoft repair - I removed all my Add Ins, etc. to no avail. Outlook would just stall every time. I started thinking and thinking....and when anything stalls it can be because of security reasons - it is because the router will sometimes kick it out as a threat.

So, I restarted my router, restarted my computer - and restarted my Outlook - and it has been working fine ever since.

Not to say, this is a solution for every problem - but it actually worked for my Outlook 2010 which stalled every time I hit the Insert button. Somehow I made the router unhappy. I had been downloading PDF forms from the IRS website - maybe it's the IRS my router does not like. Imagine that.

noel_9541's picture

I know this is long outdated, but might still help someone who stumbles across this website searching for an answer, as I did.

This puzzled me for some time until I did a help search in Outlook which didn't answer the question directly, but gave me a clue in the form of the words "Pop Out". It goes like this:

When you reply to an email, there are 2 options at the top left of the reply pane.

One is "Pop Out". If you click on "Pop Out", it pops your reply into a new little window and the "attach" commands are there again. Simple as, but not obvious. :)

The other is "Discard", which discards the reply you are typing, and isn't relevant to this post, but just completes it.

Hope this helps someone with the "Can't attach files to a Reply" problem.