Google Mail, How To Fix Gmail Attachment Failed Errors

Gmail, like any other modern email service, supports file attachments that are then send with the email to the recipient of the email. File attachments need to be uploaded and match certain criteria before they are attached, or added, to the email. It is for instance not possible to send executables directly via Gmail.
Users may get error messages like "Attachment failed" or "Attachment failed. This may be due to a proxy or firewall" when they try to upload attachments to Gmail.
This guide is a collection of fixes and suggestions that may help resolve attachment failed type of messages in Gmail. Attachment failures have different causes, which means that there is no single fix available that resolves all the issues.
I suggest you try each method on its own by returning to the compose mail window and trying to add the attachment. If it works congratulations, you have resolved the attachment failed message. If it does not try the next option in line.
Attachment Failed Basic Help
You may want to try the following tips first before you try the advanced tips in the next section.
Adobe Flash
Make sure you are running the latest version of Adobe Flash. The default attachment uploader is using Flash for the uploading of files. Old Flash versions may no longer be supported by the uploader or return error messages.
Visit this page to check your Flash version and compare it with the latest version of Flash posted on the same page.
Web Browser
- Make sure you have the latest version of your web browser installed. Depending on your browser you can either check for updates directly in the browser, or need to visit the developer website to see if you are running the latest version.
- You may also want to consider switching browsers to see if that resolves the issue.
- Make sure your browser is not in offline mode, especially so if you are using Microsoft's Internet Explorer.
- Try disabling the web browser proxy if one is configured.
Attachment Uploader
Gmail has an option to switch from the advanced uploader to a basic attachment uploader. This is done with a click on the gear icon in the upper right corner of the screen and the selection of Mail Settings. Locate Attachments under the General tab and switch from Advanced attachment features to Basic attachment features there.
Different Computer
Maybe you have access to a second computer, preferably at a different location. You can try to upload attachments on that computer to see if you experience the attachment failed issue there as well.
If you do not you know that it is not account related, but network or computer related. You may then want to check your firewall and security software settings to make sure that they do not interfere during attachment transfers to Gmail.
Advanced Tips Fixing Attachment Failed Messages
Desktop email
Using Gmail over the web is only one option for users. You can alternative download and install a desktop email client like Thunderbird or Microsoft Outlook. Configuration is not difficulty, see Setting Up Email Accounts In Thunderbird 3 for help on that.
Disabling HTTPS
Please note that it is usually not recommended to disable HTTPS. You may want to give it a try though if you have tried all other options.
You can disable it under the General tabs of your Gmail settings. Locate Browser Connection near the top and switch from Always use HTTPS to Don't Always use HTTPs.
Contact Google
While there is no way of telling that Google will respond to your report, it may be better than giving up right away on resolving the issue.
Head over to the Gmail support contact form and send Google an email, telling them exactly what happens, and what you have tried so far.
Closing Words
There are lots of workarounds available to resolve attachment uploading problems on Gmail. If nothing helps, you may want to consider using a different email service after you have tested that attachment uploading works there.
Have you ever had problems uploading attachments to Gmail? If so, did you resolve those issues?
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You said that Outlook isn’t your main email client, so which is your main one?
I think its thunderbird
It is Mozilla Thunderbird.
Awesome! This actually solved my problem… what a stupid bug.
If this is the same bug that I’ve encountered, there may be another fix: (1) hover over open Outlook item in Taskbar, cursor up to hover over Outlook window item, and right-click; (2) this should give you Restore / Move / Size / Minimize / Maximize — choose Move or Size; (3) use your cursor keys, going arbitrarily N/S/E/W, to try to move or size the Outlook window back into view. Basically, the app behaves as though it were open in a 0x0 window, or at a location that’s offscreen, and this will frequently work to resize and/or move the window. Don’t forget to close while resized/moved, so that Outlook remembers the size/position for next time.
THANK YOU Claude!!! I could get the main window to launch but could not get any other message window to show on the desktop. You are my hero!!!!
Solved my issue! 6 years later and this is still problem…
Fantastic. Thank you. Size did the trick.
This solved my Outlook problem, too. Thank you. :)
Thank you so much, this started happening to me today and was causing big problems. You are a life saver, I hope I can help you in some way some day.
You are a god – thank you!
thanks a lot…. work like charm.. :-)
Yah…thanks Claude. I’ve been having the same problem and tried all the suggestions…your solution was the answer. It had resized itself to a 0/0 box. Cheers
Excellent post. This had me baffled even trying to accurately describe the problem. This fixed it for me.
Thank you
Thanks a lot for the article. Don’t know why it happenend, don’t know how it got fixed, but it was really annoying and now it works :-)
Thanks a lot. I was facing this issue from past 3 week. I tried everything but no resolution. The issue was happening intermittently and mainly when I was changing the display of screen ( as i use 2 monitors). The only option i had was to do system restore. But thanks to you.
I’ve been tried to sole this problem for 12hours. Your comment about changing the display of screen helped me a lot!! Thanks!!
Thank you…don’t know why this happened but your instructions helped me fix it. Running Windows 10 and office pro 2007
Great tip! Thanks!
Worked for me, too – thank you!!!
It’s Worked for me, too
thank you very much!
I had a similar issue with Outlook 2013 on Windows 10 and this helped me to fix it. Thank you very much!
Thank you so much. Solved!
Considering you published this in 2012, incredible not been debugged by Microsoft.
Thank you again. M
This problem was faced by only one user logging to TS 2008 r2 using outlook 2010.The issue was resolved.
Thanks.
Great tip. Thank you!!!! If it helps, I had to use the Control Key and the arrow keys at the same time to bring my window back into view. Worked like a charm.
Thank you, this worked !!!!
Man, you are a fucking god. Thanks a lot, what an annoying bug!!
Awesome, this post solved the issue. Many thanks!