Outlook Forwarding Not Working? Our Investigation After Testing 50,000+ Microsoft Accounts
Outlook Forwarding Not Working? Our Investigation After Processing 50,000+ Microsoft Accounts
Published by the FoxSoft Team
Last Updated: July 2026
Introduction
For years, Microsoft Outlook has included a built-in feature that allows users to automatically forward incoming emails to another address.
For many businesses, marketers, account managers, and anyone managing multiple email accounts, this feature has been essential.
Then, something changed.
Around June 2026, our support team started receiving reports from customers who could no longer enable forwarding on Outlook accounts.
The process looked completely normal.
Forwarding could be enabled.
The destination email could be entered.
The settings appeared to save successfully.
But after refreshing the page…
Everything disappeared.
No error message.
No warning.
No explanation.
At first, we assumed it was a temporary Microsoft issue.
Then another customer reported the exact same behavior.
Then another.
And another.
Within days, it became clear that this wasn’t an isolated incident.
Because the FoxSoft team processes more than 50,000 Microsoft email accounts every year, we were in a unique position to investigate the issue using a much larger sample size than the average user.
Instead of testing one or two accounts, we were able to compare thousands of Outlook, Hotmail, and Live accounts across different account ages, countries, browsers, IP addresses, operating systems, and security configurations.
What started as a simple support ticket quickly turned into a month-long investigation.
This article documents exactly what we observed, what we tested, and the pattern that consistently appeared throughout our testing.
One important note before we begin:
This article does not represent an official statement from Microsoft.
Everything below is based on our own testing and observations while working with a large number of Microsoft accounts.
Timeline of the Investigation
June 2026
The first customer reports arrive.
Several users report that Outlook forwarding settings disappear immediately after being saved.
At this stage, we assume it’s simply a temporary Microsoft bug.
Late June 2026
More customers begin reporting the exact same problem.
Our internal team starts testing the issue across different environments.
Early July 2026
Testing expands significantly.
We compare:
- New Outlook accounts
- Old Outlook accounts
- Hotmail accounts
- Live accounts
- Different countries
- Different browsers
- Different IP addresses
- VPN connections
- Residential connections
- Fresh Windows installations
Despite changing nearly every possible variable, the issue remains.
Mid July 2026
After hundreds of additional tests, one pattern begins appearing repeatedly.
The issue no longer appears random.
Instead, it seems closely related to the security history of the Microsoft account itself.
Why We Decided to Publish This
Normally, internal investigations like this stay within our support team.
However, after searching online, we found thousands of users asking the same questions:
- Why does Outlook forwarding disappear?
- Why won’t Outlook save forwarding settings?
- Why is Hotmail forwarding not working?
- Why does Outlook remove my forwarding address after saving?
Unfortunately, most discussions ended without a clear answer.
Rather than keeping our findings internal, we decided to publish everything we observed in the hope that it helps others experiencing the same issue.
If Microsoft changes the behavior in the future, we’ll update this article accordingly.
What We Wanted to Find Out
Before running any tests, we wrote down a simple question:
What causes Outlook forwarding settings to disappear immediately after saving?
That question became the foundation of every test we performed over the following weeks.
Instead of looking for assumptions, we focused only on one thing:
Finding patterns supported by real-world testing.
What We Tested
Once we realized the issue was affecting far more than a handful of users, we stopped looking for quick fixes and started treating it like a technical investigation.
Our goal wasn’t to prove a theory.
Our goal was simple:
Identify exactly what these accounts had in common.
Instead of changing multiple variables at once, we changed only one variable per round of testing.
This allowed us to eliminate possible causes one by one.
Test Environment
Over the following weeks, we tested Microsoft accounts under dozens of different conditions.
The variables included:
| Variable | Tested |
|---|---|
| Outlook.com accounts | ✅ |
| Hotmail.com accounts | ✅ |
| Live.com accounts | ✅ |
| Newly created accounts | ✅ |
| Older accounts | ✅ |
| Multiple browsers | ✅ |
| Different Windows installations | ✅ |
| Residential IPs | ✅ |
| VPN connections | ✅ |
| Multiple countries | ✅ |
| Different ISPs | ✅ |
Every test followed the exact same process.
- Sign in.
- Open Outlook Settings.
- Enable Forwarding.
- Enter destination email.
- Save.
- Refresh the page.
- Check whether forwarding remained enabled.
Simple.
Repeatable.
Easy to verify.
What Didn’t Matter
One of the biggest surprises was how many commonly suggested “solutions” made absolutely no difference.
Changing browsers didn’t help.
Changing computers didn’t help.
Using another VPN didn’t help.
Changing IP addresses didn’t help.
Trying another country didn’t help.
Even completely fresh Windows installations produced the same result.
After enough testing, we became confident that the issue was not related to the local computer.
It also didn’t appear to depend on:
- Browser cache
- Cookies
- Windows version
- Internet provider
- Geographic location
Those variables consistently produced the same outcome.
The Turning Point
After eliminating nearly every environmental factor, we shifted our attention away from the computer…
…and toward the Microsoft account itself.
Instead of asking:
“What’s wrong with this PC?”
we started asking:
“What’s different about these accounts?”
That question changed everything.
The Pattern We Couldn’t Ignore
As our dataset continued growing, something unexpected happened.
Accounts slowly started separating themselves into two very different groups.
One group could save forwarding settings without any problems.
The other group almost never could.
At first, we assumed it was coincidence.
But every additional test reinforced the same observation.
Eventually, the pattern became impossible to ignore.
Group One
Older Microsoft accounts.
Previously verified.
Forwarding saved normally.
Settings remained after refreshing.
No issues.
Group Two
Newer Microsoft accounts.
Or older accounts that had never completed Microsoft’s previous phone verification process.
Forwarding appeared to save…
But disappeared immediately after refreshing the page.
Exactly the same behavior.
Every time.
An Interesting Observation
Years ago, Microsoft allowed users to verify their accounts using a phone number.
Many older Outlook users completed this verification without giving it much thought.
Today, that option is no longer available for newly created accounts.
The phone verification page has largely disappeared from the account security process, leaving many users unable to reproduce the same verification state as older accounts.
This immediately caught our attention.
Could there be a connection?
An Important Disclaimer
At this point, it’s important to make something very clear.
We are not saying that phone verification is officially required for Outlook forwarding.
Microsoft has never published documentation stating that.
What we’re saying is something different.
Based on our testing, accounts that had previously completed Microsoft’s historical phone verification process consistently behaved differently from accounts that never had the opportunity to complete it.
That distinction matters.
We’re reporting an observation.
Not claiming Microsoft’s internal logic.
Our Confidence Increased Over Time
One successful test proves very little.
Ten tests are interesting.
One hundred tests begin to reveal patterns.
When you’re working with more than 50,000 Microsoft accounts every year, repeated observations become much harder to dismiss as coincidence.
Every new batch of testing continued pointing toward the same conclusion.
Not because we wanted that conclusion…
But because the data kept leading us there.
A Note About Exceptions
Like almost every large-scale technical investigation, there were occasional edge cases.
Technology is rarely 100% predictable.
However, despite those rare exceptions, the overall pattern remained remarkably consistent throughout our testing period.
That consistency is the primary reason we decided our findings were worth publishing.
Why We Believe This Is Happening
At this point, we had enough evidence to identify a consistent pattern.
The next question became much more difficult.
Why would Microsoft allow forwarding on some accounts, but silently reject it on others?
Unfortunately, we don’t know.
Only Microsoft can answer that with certainty.
However, after several weeks of testing, we developed a theory that best explains the behavior we observed.
Our Working Theory
Email forwarding is a surprisingly powerful feature.
When enabled, every incoming email can automatically leave Microsoft’s infrastructure and be delivered somewhere else.
For legitimate users, this is extremely useful.
For attackers, it can also be extremely valuable.
Imagine a compromised Outlook account.
If an attacker enables forwarding without the owner’s knowledge, every future email could be copied elsewhere.
Password reset emails.
Bank notifications.
Verification codes.
Business communications.
Everything.
Because of that, forwarding has long been considered a high-risk account setting.
It’s reasonable to assume Microsoft wants to be very careful about which accounts are trusted enough to use it.
Again…
This is our interpretation of the behavior we observed.
Not an official Microsoft statement.
Why Older Accounts Behave Differently
One thing became increasingly obvious during our testing.
Older Microsoft accounts often carried a much richer security history.
Many had:
- Previous phone verification
- Long account age
- Years of successful sign-ins
- Established usage patterns
- Recovery information configured
New accounts rarely had any of those characteristics.
From Microsoft’s perspective, those two accounts may not represent the same level of trust.
Whether forwarding decisions are based on one factor or dozens of internal signals, we can’t know.
But the difference in behavior was impossible for us to ignore.
What This Doesn’t Mean
One mistake we want readers to avoid is assuming that phone verification alone unlocks forwarding.
That is not what our testing proves.
Instead, our findings suggest something much broader.
Older accounts that had previously completed Microsoft’s historical phone verification process consistently behaved differently from accounts that never had that opportunity.
Phone verification may simply be one signal among many that Microsoft considers when evaluating account trust.
There could be dozens of additional signals involved that are completely invisible to users.
Why No Error Message?
Perhaps the most frustrating part of this entire issue is that Outlook doesn’t explain what’s happening.
From the user’s perspective…
Everything appears successful.
You enable forwarding.
You enter the destination address.
You click Save.
Nothing looks wrong.
Only after refreshing the page do you discover that your settings never actually remained enabled.
No warning.
No explanation.
No indication of which requirement wasn’t met.
That silence is what makes troubleshooting so difficult.
Many users naturally assume they made a mistake.
In reality, the issue appears to be far more complex.
Common Advice That Didn’t Work
During our investigation, we found countless forum posts suggesting different fixes.
Some users recommended switching browsers.
Others blamed cookies.
Some suggested reinstalling Windows.
Others believed it was caused by VPNs.
We tested nearly all of those suggestions.
None consistently resolved the issue.
That doesn’t necessarily mean those solutions never help.
It simply means they didn’t explain the pattern we repeatedly observed across a much larger number of accounts.
So… Can This Be Fixed?
This is probably the question we receive most often.
Unfortunately…
For accounts affected by this behavior, we have not found a reliable method that consistently restores Outlook forwarding.
If Microsoft changes how account trust is evaluated in the future, this may change.
But based on everything we’ve observed so far…
This appears to be a server-side decision rather than something users can fix by changing settings on their own computer.
Why This Matters Beyond Forwarding
At first glance, this might seem like a small inconvenience.
After all, it’s “just email forwarding.”
But for many businesses, it’s much more than that.
Some companies manage hundreds of Outlook accounts.
Others use forwarding to centralize customer support.
Marketing teams rely on it to monitor shared inboxes.
Developers use it to collect verification emails during testing.
Losing this functionality can disrupt entire workflows.
That’s one of the reasons we decided to document our findings publicly instead of keeping them inside our support system.