Filed under: E-mail, Productivity, Google, Freeware, Web
Using Gmail as an impromptu drop-box for any file type
If you have the ability to install software on your work computer, by far the easiest way to move files back and forth between your home and work computer would be a file synchronizing product like DropBox. But if you don't, what's the best way to move a relatively large file between two remote computers? For small files, email is usually the answer, and for users of Gmail that expands to files of up to 25 MB in size. But with what can often be a big catch: Gmail won't allow you to transfer executable files, even if they are inside a zip archive.
However, if you're simply wanting to move a file between computers, you can exploit the fact that Gmail doesn't actually scan a file to see if it is an executable until you actually try to send the email containing the file. This means that you are free to attach any file up to 25 MB in size to an email in Gmail, as long as you don't send it. You can then log into your Gmail on another computer, and download the attached file, without ever running into the executable file restriction.
Of course, the other easy way around Gmail's limitation is to change the file extension of the file you are sending. If you have an executable file inside a Zip archive, and you change the archive's file extension from .zip to .zzz, for example, Gmail doesn't know what a .zzz file is and does not scan it. Voila, you can now easily send executable files through Gmail.

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They key to getting good at Graveyard Shift is learning to use ...

Reader Comments (Page 1 of 1)
Alex M said 1:57PM on 6-30-2009
I always have trouble sending large attachments. It's probably my crappy upload speed, but still, I don't think gmail's upload script is very robust.
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Money Mike said 2:47PM on 6-30-2009
Before I got to the last paragraph, I was already playing that scenario out in my head and wondering what would happen if I just renamed the file extension. Jason, you gave the example of putting an exe in a zip file and renaming the zip to zzz, but could you save a step and just rename the exe to something different?
I think this is a great idea, but I have to admit I probably won't use it much. I just feel more comfortable saving it to my flash drive.
I've been starting to use gmail more and more lately, so I've been keeping my eye out for any tricks, and this is a good one. It's not groundbreaking and probably not news to a lot of users, but it's a good idea to keep in mind. Thanks.
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Panhandler said 4:17PM on 6-30-2009
"If you have the ability to install software on your work computer, by far the easiest way to move files back and forth between your home and work computer would be a file synchronizing product like DropBox. But if you don't...."
USE PORTABLE DROPBOX!
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John said 5:27PM on 6-30-2009
Try Live Mesh. You can sync folders across multiple computers (up to 5GB) and easily access the rest of your other computers with its built in remote desktop functionality.
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WinterTiger said 5:49PM on 6-30-2009
@Money Mike
Yeah, you can rename the exe file directly, I just go from .exe to .ex_ and it works fine. Been doing that since I got my gmail account actually...
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Satish Mummadi said 8:29PM on 6-30-2009
i've been doing this in gmail since a loong time; it;s a very useful hack
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Eric H. said 10:04PM on 6-30-2009
I have been renaming executable files to send them to myself for years now with Gmail. I never thought about just not sending the email though. That is a nice trick.
I only hope that with you opening pandora's box of sending executables to yourself Gmail will not simply start scanning the header of the file to see whether or not it is a zip archive or an executable file. Of course that would in theory go against Google's motto eh?
Remember google staff! "Don't be evil"!!
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Grayson said 2:55AM on 7-01-2009
I always just stick the file in a password protected 7-zip archive. They'll never be able to scan that.
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WinterTiger said 2:37PM on 8-17-2009
They could just block all archive formats...don't give them ideas.