Yesterday a friend asked me to help with a problem he was having. The friend is not a techie and he has little interest in experimenting with software, but he is not stupid and he can follow instructions.

He used to be happy with the email service provided by his ISP, but that was discontinued and he was forced to turn to Gmail instead. He doesn’t like it as much but he has learned to live with it. He has a Google account because that seems to be a requirement to get Gmail, but he doesn’t use or want any other Google features.

He hates webmail and just wants a popmail client like he used to have. After Outlook Express was killed he turned to Outlook, which he paid for. He currently uses it on a laptop running Windows 8.1. He specifically does not want to upgrade to Windows 10 because every upgrade of every kind he has ever experienced has been a nightmare for him. I sympathise.

Until recently, Outlook worked well for his purposes with the Gmail account. He had it set so he could use it as a desktop client and it would send and receive emails through the Gmail account. In practice, it worked pretty much just like his old popmail account with Outlook Express.

Then Google changed something. I’m not sure what, and my friend wasn’t able to explain it clearly, but the result was that Outlook stopped working with Gmail. He tried to troubleshoot it himself and changed various settings according to information he found on different sites as well as some communications from Google, but he hasn’t been able to get it to work again.

I took a look at it and it seems fairly straightforward. I checked the technical settings in Outlook and some were wrong so I corrected them but we still couldn’t get it to work. We checked the password several times, which was working on webmail, and we even changed it (also in Outlook) just to see if that would make a difference but nothing seems to help. Outlook says the login is being rejected as incorrect, but in usual Microsoft fashion it doesn’t offer any other information. Just ‘there has been an error’. D’oh.

I have gone through everything multiple times. I cannot find anything that is incorrect. We have tried every variation of every parameter we can think of. All we get is the stupid ‘there has been an error’ error. Outlook does connect to Gmail, but the login keeps failing. We have at odd times seen cryptic Google messages about security being too weak or something to that effect, but I’m not sure what that relates to, if anything. We have no problem logging into Google Accounts and Gmail from the Chrome browser.

I am not on my friend’s computer so cannot give further details or do any diagnostics at this time. But I was thinking that this problem might sound familiar to someone and maybe there is a simple answer that I have overlooked. If so, I would be glad to hear any suggestions, but nothing about upgrading or trying Thunderbird instead. My friend just want to get what he is used to working again.