Outlook.com/hotmail legitimate email landing in junk folder (junk settings previously set & senders are contacts)

Question

Outlook.com/hotmail legitimate email landing in junk folder (junk settings previously set & senders are contacts)

Tim Irving 0

It looks like Microsoft took away the ability for paying customers (I have a M365 subscription) to raise tickets to document problems. Not a great look for customer service for subscription service, customers expect to work as per the documentation.

Something changed on Microsoft's email servers again, legitimate email is landing in my junk box. The sender domains are on my safe sender list and many of the individual senders are in my contacts with the "Trust email from my Contacts" toggled ON. I move the email from Junk to a folder under my inbox (Was In Junk) in order to keep an inventory of all impacted emails, so I can readily provide examples. I'm ready to roll, if I could get to support.

Back in 2023 (May - September) the same thing happened. They fixed it for a while in June 2023 but it came back again in July 2023. It was pulling teeth to get Microsoft to admit the problem existed on their servers and it had to be handled by Tier 3, Tier 1 was no help, all they did was go through the script every time and Tier 2 finally realized it was above their heads. I have ticket numbers 1057<removed PII>, 1056<removed PII>, 1056<removed PII>, 1055<removed PII>, 1055<removed PII>, 1055<removed PII>, 1053<removed PII>, 1055<removed PII>, 1055<removed PII>, 1053<removed PII>, 1053<removed PII>, 1052<removed PII>. It was Jaspreet finally fixed it under ticket 1057<removed PII>, server side changes were needed.

Tim Irving 0 Reputation points

2026-05-08T17:34:17.5433333+00:00

Already rejected the AI reply, it regurgitated the help document I already looked at and implemented back in 2023. Nothing has changed on my side. After blindly poking more, I got to chat support. It's there but you have to try multiple times apparently. The first time it said Chat is not available and pushed me to the community. Yeah. Spoke too soon, the rep told me the chat was ending & follow instructions at the end of the chat. They went away when the chat closed. The gist, it sending me back through support via a link in Outlook.com. I waited longer than the requested 5 minutes, guess what now. No matter how many times I try to get to support, I keep getting sent to the Community. Anybody have a trick to get the official Microsoft page to give up a support link? https://support.microsoft.com/en-us/office/microsoft-365-customer-service-and-support-96162163-b3aa-498b-bbbb-5e757b0f31da#articlefootersupportbridge=contactusbridge

1 answer

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Tim Irving 0 Reputation points

2026-05-08T17:34:17.5433333+00:00

Already rejected the AI reply, it regurgitated the help document I already looked at and implemented back in 2023. Nothing has changed on my side. After blindly poking more, I got to chat support. It's there but you have to try multiple times apparently. The first time it said Chat is not available and pushed me to the community. Yeah. Spoke too soon, the rep told me the chat was ending & follow instructions at the end of the chat. They went away when the chat closed. The gist, it sending me back through support via a link in Outlook.com. I waited longer than the requested 5 minutes, guess what now. No matter how many times I try to get to support, I keep getting sent to the Community. Anybody have a trick to get the official Microsoft page to give up a support link? https://support.microsoft.com/en-us/office/microsoft-365-customer-service-and-support-96162163-b3aa-498b-bbbb-5e757b0f31da#articlefootersupportbridge=contactusbridge

Answer 1

Somil Jain 660

hi Tim Irving
Unfortunately, a lot of people have reported that loop recently — the support flow often redirects paying Outlook.com/M365 users back to the community instead of exposing live support options consistently.

A few tricks that sometimes help force the support/contact options to appear:

Use an InPrivate/Incognito browser window.

Make sure you are signed into the subscription account before opening the support page.

Try from:

Outlook.com → Help → Help → “Contact Support”

  instead of starting from the public support site.
  
  Disable ad blockers/script blockers temporarily.
  
  Try different browsers (Edge tends to expose Microsoft support options more reliably).

Some users also report the chat option only appears during certain hours or after navigating through:

Billing

Subscription

Technical issue multiple times.

Given your previous ticket history and the fact that settings already match documented guidance, this really does sound like something that may require escalation beyond normal Tier 1 scripts again.

If my answer is useful for you, please hit Accept the answer to support me.

Thank you so much,

Tim Irving 0 Reputation points

2026-05-09T15:00:24.0666667+00:00

Thank you for the ideas. I was unable to navigate Billing - Subscription - Technical Issue Multiple Times, I know I've seen this option in the past but it's nowhere to be found at the moment. I tried your recommended steps and still land with Community link not a support link. Copilot gave me the verbiage to use to escalate the ticket but could not open a support chat window.
Somil Jain 660 Reputation points

2026-05-09T15:14:10.7333333+00:00
At this point, since you already confirmed:

the junking behavior ignores Safe Senders

trusted Contacts are still affected

settings have not changed since the previous server-side incident

and the support flow itself keeps looping incorrectly

then yes, this really should be handled through official Microsoft support escalation rather than community troubleshooting.

The support/contact flow for paid M365 consumer accounts is supposed to expose escalation paths, especially for mailbox filtering issues affecting subscribed services.

One path that should normally work is:

Outlook.com

Help

Support

Contact Support

while signed directly into the subscribed Microsoft 365 account in Edge/InPrivate mode.

Another route that often works more reliably is:

Microsoft Account → Services & Subscriptions

Select Microsoft 365 subscription

Get Support / Contact Us

Given your previous Tier 3 history and the fact that server-side fixes were required before, I do think continued escalation is justified here.

If my answer is useful for you, please hit Accept Answer to support me.

Thank you so much.
Tim Irving 0 Reputation points

2026-05-09T16:40:54.81+00:00

If you have any ideas on how to get the support link to appear when I go to Contact Support, I'm all ears. It does not appear, only the Community Link. I've tried repeatedly both navigation paths - except for trying Edge. You just taught this old dog a new trick, Edge is available for Mac. Edge didn't give me any edge in getting support to appear. Both your answer & Somil's answer should work if Microsoft is willing to play. Thank you for taking the time to provide insights.
Somil Jain 660 Reputation points

2026-05-09T17:26:58.3766667+00:00
At this point I really think the issue is the support-routing system itself rather than anything you're doing wrong.

One thing I would still try is going through a completely unrelated support path first for example:

Billing

Microsoft account

Subscription management

Sometimes once you get any live agent, they can internally transfer the case to Outlook.com support even if the direct Outlook support flow keeps redirecting to Community.

You could also try using:

the Microsoft 365 mobile app

or the Get Help app on Windows

since those occasionally expose contact/chat options differently from the web portal.

Another thing that sometimes works is temporarily disabling VPNs, privacy filters, DNS filtering, or content blockers because Microsoft's support pages rely heavily on scripts and redirects.

Given your previous Tier 3 case history and the fact that backend changes fixed this before, I do think continued escalation is justified here. It definitely does not sound like a normal mailbox-side configuration issue anymore.

Hopefully Microsoft fixes both the filtering behavior and the broken support routing, because I can understand how frustrating this must be as a paying subscriber.

Thank you so much.
Tim Irving 0 Reputation points

2026-05-13T15:48:56.4266667+00:00

FYI, I got lucky & connected with a rep, when I tried another support product's support chat. The rep shut me down cold, provided the same stock instructions on how to access Outlook support. I appreciate everyone taking time to chime in, unfortunately Microsoft doesn't want to provide support.
Tim Irving 0 Reputation points

2026-05-13T21:47:16.7666667+00:00

Can someone help me understand why the original post was edited to remove "PII"? What makes the ticket number PII? Without a ticket to reference others with this problem (if they can get to support) will start with Tier 1.

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Outlook.com/hotmail legitimate email landing in junk folder (junk settings previously set & senders are contacts)

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