If you find yourself using public wifi, such as in a coffee shop or such, and suddenly you find that your email program can’t access and download or send email from Gmail, and if you are using a proxy, VPN, or other “wifi connection securing” program, that may be the problem. (From hereon out we will simply say “VPN services” as that is usually what someone would be using.)
For example, Cloak bills itself as the “super simple VPN; VPN stands for Virtual Private Network, and services such as Cloak allow you to connect through their VPN, putting their VPN between the public wifi you are on, and the places on the internet you want to go, so that your data cannot as easily be sniffed by some bad guy sitting on the public (or posting as the public) network.
(For an example of how such bad things happen to good Internet users, see our article Wifi Hotspot Evil Twins Mimic Wi-fi Hotspots and Steal Your Data.)
A great idea, right? We ourselves use Cloak, and can highly recommend it.
However, as we ourselves discovered today, Gmail will reject the connection you are trying to make with an app (program) if it recognizes that your account is trying to connect from somewhere that it hasn’t seen you before (usually geographically speaking).
And because VPN and similar services reroute you through their network, today Gmail perceived that we were trying to connect from Texas (where Cloak’s server was, and thus where the IP address from which we were trying to connect was located), even though we were actually sitting in our favourite coffee shop in Boulder.
And so, Gmail refused our connection.
Here’s how that looked:
If you didn’t get that pop-up, look in the upper right-hand corner of your mail app, and look for this:
Click on the “Login Failed” and it will give you the pop-up.
From there, click on “Open Connection Doctor”, and you will see what your email client is trying to do. As you can see from our example, Mail was able to connect to the Internet, but was unable to connect to Gmail.
We were running Cloak at the time, and knowing a thing or two about how VPNs work, we immediately suspected that the VPN – or the location of their IP address – was causing the issue.
So, we tested this by turning Cloak off.
Once our email was able to connect again to Gmail and retrieve email, we saw that Gmail had sent us this:
Clicking on “Review your devices now” brings you to this:
And Gmail acknowledges it when you confirm that it was you.
But, at least for us, clicking on “Yes, that was me” did not make one bit of difference in terms of our mail program being able to connect, it still couldn’t connect.
It turns out that Cloak, at least, even talks about this on their site, but it certainly isn’t unique to Cloak – it’s an issue (or not, depending on how you look at it) on Gmail’s end; you can think of it as the equivalent of your credit card carrier blocking your account when they notice you suddenly making a point-of-presence charge in Seattle when you live in New York.
So, what to do if you run into this situation?
What we do is switch from public wifi to using our smartphone to tether our computer and get out to the Internet when doing things online which require heightened security (such as online banking).
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