Outlook 2106 Mac OS not accepting IMAP authentication

Question

Outlook 2106 Mac OS not accepting IMAP authentication

Ian 1

I recently had to change my Rogers Yahoo email password, because the Outlook app on my mobile asked me to after it updated. It took a couple of tries, but now I can access my Rogers email on my mobiles. However, my connection via Outlook 2016 stopped working. Even entering the new password still brings up Authentication Failed. I even deleted the account and re-entered all IMAP information in. And still getting Authentication Failed message. Login info is CORRECT. Works on browsers, works on mobile app. It just doesn't work on desktop app on both my Macs running 10.11. Was working perfectly fine before the mobile update password issue. Which seems to happen quite often whenever the mobile app updates. In fact, whenever the mobile app updates, I'm certain 90% of the time, it will ask me to re-enter passwords (has happened on multiple email accounts). But this is another issue all together. Which sadly has affected my desktop app. How do I fix the issue for the Mac OS DESKTOP Outlook 2016 app?

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Answer 1

A good next troubleshooting step is to try creating a new Outlook profile, then re-configure your IMAP settings.

Start by closing completely out of Outlook (no black dot on the bottom) opening the Outlook Profile Manager app:

https://support.microsoft.com/en-us/office/manage-profiles-or-identities-in-outlook-for-mac-fed2a955-74df-4a24-bef6-78a426958c4c

Then click the + button and give the profile a name. Highlight the profile you just made and click the gear button then Set as Default.

Now launch Outlook again and put in your IMAP settings. I believe these are them:
https://ca.help.yahoo.com/kb/rogers/SLN4075.html

If this doesn't work, try clearing anything that has to do with Yahoo from your Keychain. Make sure Outlook is closed when you do that.

Answer 2

Thanks rsammas, but none of your suggestions worked. I even reinstalled Outlook. And nadda. The only thing I can think of that I haven't tried, is updating to a newer Mac OS. But I would wager that won't solve my issue. It was working before, than it wasn't. All because of the issues I had with the mobile app for iOS. It stopped working after that issue. But like I mentioned, I'm able to access through the mobile app. Just not the desktop anymore. Microsoft has gotten more and more crappy. Even the webmail Hotmail or Outlook, is terrible. Sooooooooo slow. And it's not my internet connection. All other connections are super fast. Just not Microsoft stuff.

Guess I'm just going to have to ditch Outlook, for something better. Which sucks, because I've been using for years. And all my database of archived old emails are attached to Outlook. I'd have to start from scratch again. Such a pain!

Unless you have any other tips I can try? Cheers

Answer 3

rsammas 171

You most definitely should upgrade to a newer version of macOS. 10.11 hasn't gotten a security update in over 3 years, so it's most likely riddled with security issues.

Its also possible your email provider made some modifications to their supported authentication methods and either macOS 10.11 or Outlook 2016 just doesn't support the new method.

Ian 1 Reputation point

2021-03-24T21:48:05.863+00:00

I'm one of those people that doesn't like to update if my system is running just fine. I've been using Macs since 1990. It used to be great. But every update after Snow Leopard, has become problematic for me. And took me days to fix. It got to a point where I just learned, if it ain't broke, don't update it. And only updating when I really need to. Eg. New software I need requires a newer version of the Mac OS. So I'm saving the hassle of running into issues that will take days for me to fix. I'm also on an older 2010 Mac Pro (still a workhorse). And I can't update pass 10.14. Updating to 10.14 will probably just bog down my system anyway. And even with these issues, I still prefer the Mac OS over Windows (I use Windows for my F/T job).

But regardless. The solution I found seems to be working. And my system is running fine with no issues (security or otherwise). When I NEED to update, I'll update then. Cheers.

Answer 4

Found a "fix". I'm hoping it sticks. When I logged in via browser, I got a notice saying that I may need to Generate An App Password. I clicked on the link to do so, and it took me here. https://rogersmembercentre.com/rmcapp/remc.html#/accountInformation

I chose Authorized Applications. Then followed the steps. I created a Rogers. And entered the one time generated password (not the password I had created to access my Rogers email account). Boom. It connected and started syncing. I tried using the same password for my other Mac (Outlook went south on that one too), but it didn't take. No connecting and syncing. But then I thought, let me create another App Password for that Mac. Entered that password, and boom. That one started connecting too. Rogers! Oy vey! Would've been nice of them to inform people of this issue. Nothing in Google or on their help site. I found and tried it by chance. Hope this helps anyone else having issues connecting to a Rogers email account.

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Outlook 2106 Mac OS not accepting IMAP authentication

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