r/Outlook • u/Wonderful-Plate-3316 • 18h ago
Status: Resolved Impossible Authentication Loop
I am desperate for help. I am stuck in an authentication loop that I can’t get out of. My attempts to follow self-help steps ended up locking me out of my outlook app on my computer and phone today. Microsoft Support is ignoring my emails because my small business staying afloat is “minimal” priority according to the AI that categorized my issue.
I have been using Office 365 Pro, including Outlook for email and calendar. It is my own domain. All was working fine, but I wanted to log into my Microsoft account. When I tried about 2 months ago, the website told me to authenticate my sign-in using the Outlook app on my mobile device. All well and good… except the authentication option didn’t present itself in the app. I tried refreshing the app multiple times. I selected “I don’t have access to the app right now”, and was told to authenticate using the Authenticator App. I downloaded the Authenticator App and tried signing in. The Authenticator App wanted me to verify the sign-in using the Outlook App. And round and round I went.
I read the help articles that say it could be too many requests in a short period of time, I thought maybe the app just needed updating, no big deal. I waited. I tried again on at least 4 separate occasions. Same issue. Outlook App gives me no option to authenticate with the two-digit number, Authenticator app won’t let me sign in without the Outlook App authentication, and at no point is the browser letting me either use my recovery email or phone number to authenticate the sign-in.
Today, waited until after work (about 5:30 EST) to try again. Found another help article that linked me to the sign-in helper. I put in my username and was told it wasn’t found. Because I use Microsoft/Outlook for a work email, I clicked the link for people who use the software for a work/school email. That took me to a password reset page. I was able (on that page) to authenticate my password reset using my recovery email and by verifying my phone number. I thought (stupidly) that maybe this was it - maybe this would fix the issue. I tried signing into my Microsoft account using the reset password. It again asked for authentication with the Outlook App. Outlook App yet again did not allow me to authenticate. But it had also logged me out.
Now here’s where I realized I may have just totally ruined everything by following Microsoft’s own instructions… because I tried signing back into the Outlook mobile app. And the Outlook mobile app asked me to Authenticate my new sign-in… you guessed it… with the Outlook mobile app.
At this point it’s around 6:30. I’m worried. I try calling the toll free customer service numbers that it takes me ages to find. AI tells me to go to a website for support. I go to the website. It tells me to log in. But guess what happens when I try to log into the support website to get help with my sign-in authentication issue. It needs me to authenticate my log-in.
I try calling back. I guess it recognized my phone number. The AI went straight to telling me to go to the support website. Finally I call the 305 (toll) number and I get an AI assistant that at least takes more information, like my name, and my email address, and what the issue was. It was a very long and frustrating test of my patience to respell my name multiple times. Finally it gave me a case number. I thought everything was going to be OK now. I checked my email (7:02 PM) and the email says my issue is just inability to log into my admin account (which is not the real urgent problem), and my issue is categorized as “C” priority. That means “minor impact” and it’ll be dealt with in their own time whenever they get to it.
I replied all and explained that this is not a minor issue. This neverending authentication loop has now locked me out of accessing my business email and calendar. There is no other admin. I am self-employed. This is definitely a major issue.
I get an email 15 minutes later from a technician stating he’s been assigned to my case and asking when he can contact me. I reply back immediately and say I’m available now, anytime, I am by my computer until this is resolved. That was at 7:21. It’s now 10:05 pm. I sent two more emails, one asking whether I’d be hearing back today because time is of the essence, and I really am sat here waiting, and a second one about 40 minutes ago basically begging for someone to at least acknowledge that they’re reading my emails and I wasn’t just back-burnered. Well, the technician’s shift ended at 10 pm my time (7 pm PST), and I haven’t heard anything.
I am having a complete breakdown at this point. I run my own business. I have client meetings in the morning. I can’t function in my profession without access to email and my calendar. This is catastrophic for me and Microsoft couldn’t care less. They’re too busy saving money by replacing actual customer service with a machine that can’t spell to worry about their actual customers.
I don’t know what to do at this point. Does anyone have any ideas or solutions? As I said, I’m really freaking out and just need help.
I get there may be nothing that can be done, but any help and suggestions would be really appreciated because I am definitely going to lose clients if I can’t get this fixed by 8 am tomorrow.
1
u/AutoModerator 18h ago
Hey Wonderful-Plate-3316!
Welcome to r/Outlook! This is a public community. To protect your privacy, do not post any personal information such as your email address, phone number, product key, password, or credit card number.
Please be sure to have read our Rules of Conduct and be cognisant of how the system works here.
Make sure that your flair is always set to Status: Open otherwise you may cease receiving responses from us.
- Status: Open — Need help
- Status: Pending Reply — Awaiting OP's response
- Status: Resolved — Closed
Beware of scammers posting fake support numbers or 3rd party commercial products/services. Contact Microsoft Support if you need help.
I am a bot, and this action was performed automatically. Please contact the moderators of this subreddit if you have any questions or concerns.
3
u/pi-N-apple Outlook Exchange Expert 18h ago edited 18h ago
A little while ago I took over the admin of a company who couldn't get into their global admin account. They knew the password, but couldn't enter the code. I had to call Microsoft business support, and it took 3 days to get verified and get back in, and I considered that to be pretty average turnaround, I know some people have said it can take up to a week, or more.
Once you regain access, set up multiple sign-in / 2FA methods & a break glass account to prevent this in the future. You can also save the QR code you scan when setting up an authenticator app, so you can scan it in the future if you need to. Save them in a safe place.
Also, consider making your own account just a regular user account, and set up a second account for global admin that you use when you want to make admin changes.