GMail is a great web platform. Once you’ve signed up, you can access your email from any web browser, no matter where it is. You can have GMail pick up messages from all of your other accounts too, and centralize all of your mail (minus any spam) lives in one convenient place.
Your mail appears on a web page and you can organize, reply, or compose new messages easily. You’re interacting directly with Google’s GMail servers. Click a new message’s subject line, and your web browser fetches the contents of the message.
But having the contents of your messages zipping across the internet makes some people nervous. What if I’m reading something that’s sensitive? Business plans, proposals, online log-in credentials, banking information… these are important!
Google agrees, and that’s why they offer the option of encrypting the traffic between your web browser and their servers. They use something called “HTTP-Secure” to scramble the traffic before it’s sent, and unscramble it when it’s received at the other end. Â That way, even if someone was listening in on the network traffic, they wouldn’t get any useful information. It would look like gibberish to them.
It’s easy to turn on ‘https’ encryption at GMail, and I recommend it.
But recently I had a client who was having trouble with their company’s Google Apps accounts. They’re all GMail users, but they were having trouble attaching files to messages. Specifically, whenever they’d select a file to attach, they’d get an error message in red text that read “Attachment failed. This may be due to a proxy or firewall.”

This GMail error appeared when attempting to upload an attachment.
They were very annoyed. Google suggested using their “classic uploader” rather than their fancier advanced uploader. We gave that a try, but ended up with the same issue.
I did a quick Google search to see if anyone else may have been having the problem, and I found this discussion at Google’s help site. One method that seemed to work for most of the people was to disable the https requirement.
I was not happy about the prospect of essentially disabling the encryption, but I presented it as an option to test. It hadn’t worked for everyone in that discussion, but at least it was something to try. Â We used the administrative control panel to visit Domain Settings > SSL Â and uncheck the ‘require https connections’ checkbox.

Uncheck the "Enable SSL" box in the Domain Settings > General > SSL section of your Google Apps administration pages. You won't be as secure, but your attachments will upload properly.
Then for each user who was having trouble, we disabled https in their GMail settings.

Disable the https requirement here and save your changes. (If the radio button is disabled, log out of your GMail account and log back in.)
Our quick tests proved to be successful, attaching messages now worked just as it ought to, even with the advanced uploader.
I’ve since filed a support issue with Google, complete with screenshot and steps to reproduce. I really don’t like to compromise security in order to make GMail work as it should, so I’m monitoring this situation closely.
UPDATE: Enterprise Support was able to tell us a few days ago that they had resolved the problem. Â What did they fix? They weren’t saying. So I went back to the admin panel and re-enabled the forcing of https connections. Â We’ve found that our functionality is back! We can now attach files to messages without error messages. Â While I’m happy that things are back to normal, I would have appreciated a faster turnaround time from Enterprise Support.
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