Why are email rules in my outlook.live.com account Ignored

Question

Why are email rules in my outlook.live.com account Ignored

alan933 20

I have this rule set up and yet it sends every amazon.com email to my junk folder !!!

WHY????

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Hornblower409 5,895 Reputation points

2026-02-14T12:45:49.79+00:00

Just FYI - Your question is tagged "Classic Outlook for Windows" but your screen shot appears to be from New Outlook.

To verify which version of Outlook you have, please see this Microsoft Support article:

https://support.microsoft.com/en-us/office/what-version-of-outlook-do-i-have-b3a9568c-edb5-42b9-9825-d48d82b2257c
alan933 20 Reputation points

2026-02-14T15:19:38.59+00:00

Which proves that asking a question here and categorizing it is as confusing and convoluted as the inefficient spam folder in outlook.
Let me see , do I want to click more links to research how to determine how to determine different versions of confusing Microsoft applications...I think not.

2 answers

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Hornblower409 5,895 Reputation points

2026-02-14T12:45:49.79+00:00

Just FYI - Your question is tagged "Classic Outlook for Windows" but your screen shot appears to be from New Outlook.

To verify which version of Outlook you have, please see this Microsoft Support article:

https://support.microsoft.com/en-us/office/what-version-of-outlook-do-i-have-b3a9568c-edb5-42b9-9825-d48d82b2257c
alan933 20 Reputation points

2026-02-14T15:19:38.59+00:00

Which proves that asking a question here and categorizing it is as confusing and convoluted as the inefficient spam folder in outlook.
Let me see , do I want to click more links to research how to determine how to determine different versions of confusing Microsoft applications...I think not.

Answer 1

Hornblower409 5,895

@alan933 You are running into, what I call, the "Mother Microsoft" problem.

Your emails first arrive at the Microsoft Mail Server (in the cloud, not on your PC).

The Mail Server looks at the email and calculates a "SPAM Confidence Level" (what it thinks the chances are that this is Spam or Phishing).

If the SPAM Confidence Level is high enough (i.e. Mother Microsoft thinks this email might be bad for you) it checks your Safe Senders list, and if the email is not from a Safe Sender, it moves the email directly to your Junk Email folder, bypassing any Rules you might have.

If the SPAM Confidence Level is really high, then it will also ignore any Safe Senders you have specified and send it directly to Junk.

There are many people (myself included) who want a way to modify this behavior, but New Outlook does not have any options for this (yet).

alan933 20 Reputation points

2026-02-14T15:21:27.7066667+00:00

what ever calculating method is used, is severely flawed if it flags a major corporation like Amazon and keywords like "order confirmation" as spam. I think a high school kid's intelligence could work better than what ever heuristic is being used for that.
EmilyS_726 14,940 Reputation points Volunteer Moderator

2026-02-14T15:40:11.68+00:00

In a simple world, sure, it could work that way. But in a world full of phishing scams trying to impersonate well-known corporations, it matters that real companies like Amazon stay compliant with required email authentication so Microsoft can verify the sender is legitimate. Do you let someone into your house just because they claim they’re with the utility company, without checking their badge or verifying who they are?

I know you don’t like being educated on this, but since you’re complaining, feel free to read this thread: https://learn.microsoft.com/en-us/answers/questions/5773111/change-unverified-sender-to-verified-ie-work-relat

An Amazon employee who was also complaining about Microsoft flagging their mail was at least willing to provide the full email headers, and that made it pretty clear Amazon apparently wasn’t configuring DKIM and DMARC in a way that meets common industry expectations. So maybe take the complaint to Amazon, not here.
Hornblower409 5,895 Reputation points

2026-02-14T15:44:37.4033333+00:00

@alan933 said

flawed if it flags a major corporation like Amazon and keywords like "order confirmation" as spam.

Is it possible that your Mail Server Junk Filter is broken and will flag a legitimate email from Amazon.

That is why the mod was asking you for a copy of the message header. This allow them to examine some special fields in the header that the Junk Filter put there that indicate why it thought this was Spam.

e.g. This message header from a Yahoo email sent to me that was incorrectly getting flagged by my Outlook as Spam:

spf=softfail (sender IP is 98.137.68.205)
smtp.mailfrom=xxxxxx.us;
dkim=pass (signature was verified)
header.d=yahoo.com;
dmarc=none action=none
header.from=xxxxxx.us;
compauth=fail reason=001
X-MS-Exchange-Organization-SCL: 5

The last two lines are what I needed to figure out what went wrong.

If they don't see anything unusual in the Message Header, then they can start looking for a problem with your Outlook client instead. e.g. corrupt Rules or Blocked Senders.
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Answer 2

EmilyS726 213.8K Independent Advisor

Hello

Inbox rules only run after a message reaches your mailbox. If an email is flagged as junk, it can be marked as spam before it ever hits the inbox, and then it goes straight to the Junk folder. In that case, your rules never get a chance to override the spam classification.

If you want to dig further, you can use this instruction to get the message header of the amazon email: https://support.microsoft.com/en-us/office/view-internet-message-headers-in-outlook-cd039382-dc6e-4264-ac74-c048563d212c#tab=web

Then share a message header. Please note, please redact your personal information when you share to protect your privacy.

alan933 20 Reputation points

2026-02-13T18:01:26.18+00:00

This doesn't make sense because the rule states for an action "Move to Inbox" , meaning that it has to be somewhere else other than the Inbox....right? I would assume that it means junk folder.

Please state your microsoft reference stating that rules only run when its already in the Inbox.
EmilyS726 213.8K Reputation points Independent Advisor

2026-02-13T18:10:58.35+00:00

I didn't say inbox, I said mailbox (which includes all folders) in my first sentence.

I did say inbox in my second sentence, but that's only if the email is flagged by Microsoft before it reaches your mailbox. This is not junk mail due to the content being spammy, but it is being flagged as junk due to SPF, DKIM and DMARC issue, it is a compliance issue. If that's the case, they will go to junk folder regardless. This is why I offered to review the message header, to see if that can be the case.

https://techcommunity.microsoft.com/blog/microsoftdefenderforoffice365blog/strengthening-email-ecosystem-outlook%E2%80%99s-new-requirements-for-high%E2%80%90volume-senders/4399730
alan933 20 Reputation points

2026-02-13T18:31:21.2266667+00:00

if "mailbox" includes junk mail folder , why doesn't it run when it reaches the junk folder "mailbox"

I don't understand "SPF, DKIM and DMARC issue" too technical

What would looking at amazon.com mail headers do to resolve the problem?

Why should a user even have to poke around in deep technical aspects just to get mail from major corporations to not go into junk mail which is a very reasonable thing.

Such as .. the way gmail does not send every purchase confirmation from every company into a junk mail folder?
EmilyS726 213.8K Reputation points Independent Advisor

2026-02-13T18:45:00.6366667+00:00

I will use analogy instead -

Rules are like instructions you give your mailroom staff in your building. SPF, DKIM, and DMARC are more like the building’s security desk.

Even if you tell the mailroom “deliver everything to my office,” the security desk can still stop a package at the entrance if it fails the building’s basic verification checks. When that happens, the item gets diverted into the “quarantine area” (junk) before your mailbox rules ever get a chance to process it. That’s why a mailbox rule often cannot “run when it reaches Junk” because the spam filtering decision can happen earlier in the delivery pipeline than mailbox rules.

You don't have to poke around in the message header- I only offered it as an extra step if we want to find out for sure if that is the case. And if it is the case, the fix has to come from Amazon, not you. They need to configure their email SPF, DKIM and DMARC to meet Microsoft's requirement.

I can't speak for Gmail, but the requirement of SPF, DKIM and DMARC for business emails is still fairly new in the industry and not every email service providers implement them on the same timeline.
alan933 20 Reputation points

2026-02-13T21:14:39.09+00:00

Not needing an education, needing a solution.
EmilyS726 213.8K Reputation points Independent Advisor

2026-02-13T21:19:05.01+00:00

Sorry, didn't mean to share all of that information, only because you asked.

As I said, without reviewing the message header, I have no information to work on, to confirm for sure if that's the problem indeed, so I cannot provide any further next step.
MartMcd 2,555 Reputation points Volunteer Moderator

2026-02-13T23:44:41.1733333+00:00

Moderator note - alan933,
EmilyS726 is trying to give you answers the questions you asked, you said you didn't understand then complained when it was explained.
EmilyS762 has offered to look at the details of the email for you to investigate why the email is going directly to Junk but you have refused.

It is great that you ask when you don't understand the information given but please keep it friendly, and try not to complain when you receive the explanation you asked for.
If you work with EmilyS726, I am confident they will help you find a solution.

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Why are email rules in my outlook.live.com account Ignored

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