Google Hates Microsoft

I don’t know if that’s actually true, but it’s the best explanation I’ve got for the problem I just troubleshot for a user. This user had been using Outlook 2010 for over a year, but a couple months ago, it suddenly stopped being able to sync with one of her Gmail accounts. She asked me to look into it, and I did.

The first step was to verify the account information. I had her reset her password so I could use a test password I’d be sure worked. It did, and I confirmed Outlook couldn’t retrieve the mail for the one account. I then opened the settings for the account, which gives a screen like:


I verified the information was right then went to the More Settings page. I don’t have a screenshot of it, but here is one I saw on Google when investigating the problem:


The arrow in this indicates them telling you to change the timeout from its default of one minute to 10 minutes. I tried this, and it made no difference. I also tried both SSL and TLS encryption for the SMTP server entry as Google’s page said to do so. That also made no difference. In either case, when I’d try to test the connection, I’d be given a prompt which showed:


Which would never work despite me inputting the correct information. Instead, the box would close for a couple seconds then it’d reappear. It’d repeat this over and over and over. You would think Outlook would give up after the dozenth failed attempt, but no. The only way to stop it was to close the dialog box then manually tell Outlook to stop trying to connect. When I finally did, I was told:

Log onto incoming mail server (IMAP): The connection to the server was interrupted. If this problem continues, contact your server administrator or Internet service provider (ISP).

Which made me wonder if the ISP itself was the problem. Some ISPs block IMAP connections, and companies often block access to resources from IP ranges they believe to commonly spam/attack servers. To test this, I activated the Telnet client which came with Windows and tested the connection. It worked.

Then I realized I had been an idiot. Perhaps due to my failure to sleep last night, it took me a while to realize if the ISP had been the problem, no Gmail accounts would work with Outlook on this computer. One did, thus the problem had to be with that specific account.

Once I realized that, it was a simple task to solve the problem. I went to the Gmail webpage and started poking around. The obvious first step was to verify IMAP was enabled in the Settings menu:


It was. I checked every option in every tab you can see in that image. None were helpful. I was about to give up when I happened to click on the circle with an avatar in it by mistake. The button with the gear in it is what gives you access to the settings for Gmail. Clicking on that circle, however, gives you this:


Not believing it could be true, I clicked on the Account button and was directed to a new page, complete with its own set of tabs. I clicked on the Security tab there and found a box on it:


A couple clicks later, and “Access for less secure apps” was enabled. Two minutes later, Outlook had downloaded all the missed mail for the one Gmail account.

Why did Outlook suddenly stop working with Gmail? I don’t know. Why was there no error message alerting the user Outlook was considered too insecure? I don’t know. Why did Outlook act as though the user was inputting a wrong username/password when no username/password could possibly work? I don’t know.

I also don’t know how Google expects users to figure any of this out. Even if one knows the problem is tied to a specific Gmail account, I don’t know how one would come across this solution. Who would intuitively think to fix a problem with connecting to a Gmail account, one needs to ignore the Gmail Settings page in favor of going to a Google settings page, a link to which is not noticeable anywhere on any page? I think the answer is Google just hates Microsoft and doesn’t want to work with Outlook.

Or maybe Google is just a jerk. I went through a similarly painful process when trying to change my YouTube name. Because I had registered for YouTube with my Google name, my Google account was automatically linked to my YouTube account when Google bought YouTube. Having had no say in that, I soon found it impossible to change my YouTube display name without changing my Gmail display name as well. A sort of solution existed, but it too was buried in an obscure link you are never directed to.

Come to think of it, the “Google is a jerk” idea has a lot of weight behind it. Back when I registered my YouTube account, I specifically set it not to display my real name. When Google bought YouTube, it automatically forced YouTube to use my my Google display name. Since that was my real name, that meant it displayed my real name on YouTube despite me having specifically told YouTube not to show my real name.

Yup. Google is a jerk.



  1. Brandon,

    Google has evolved into a really nasty company. When I bought my first Android phone, it tried to force me to link to my main gmail account. I did so and didn’t like it. The only way to reverse it was to reset the phone. About 8 months ago, Google drastically changed the compose feature of gmail, and didn’t permit you to edit the subject box when replying. Also drastically reduced the size of the compose box. 99.9% of the commenters hated it. Google arrogantly refused to give users the option of using the older version of compose. I am still stuck with gmail, but now use Bing as my search engine.

    Whenever I can, I avoid Google.


  2. JD Ohio, that sounds about right. Google seems to get away with a lot because of its image. At least, I’ve seen Microsoft get slammed for things far more minor than what Google does. I’ve also seen Google’s Chrome get tons of praise for things which aren’t true. For instance, a couple years ago I complained about memory leaks in Firefox. A bunch of people, including “tech savvy” folks, told me to switch to Chrome because it didn’t have such problems. I tried Chrome, and it was every bit as bad about memory leaks. Worse yet, because Google wants to integrate its software into our computers more and more, Chrome’s memory leaks caused system instability, and I couldn’t kill the processes as cleanly.

    I still use Google products, but I have little respect for the company. I think it is every bit as bad as Microsoft (and Apple).

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