More info about Hotmail Bugs & Problems

Forwarding being disabled is mainly a protective measure by Microsoft, not a random glitch. However, while this is an intentional security feature from Microsoft's perspective, for legitimate, non-hacker users, this behavior often feels like a bug because it disrupts valid workflows and causes significant frustration.

Suspicious Activity: When you forward a large number of emails, especially from a single service, it can look suspicious to Microsoft's automated security systems. They might interpret this as a compromised account being used for spam and preemptively disable the forwarding rule to protect the platform.

Reaction to Logging In: Each time you log into your account, it can trigger a security re-evaluation. The system sees an active mass-forwarding rule, flags it as a potential risk, and disables it to ensure it wasn't set up by an attacker.

Delivery Failures: If the destination server (like Gmail) rejects even one forwarded message for any reason, Outlook might see this as a permanent failure. To protect its own server reputation from being blacklisted, it simply shuts down the "broken" rule.


Regarding delays, they are often caused by throttling. To prevent spam, Outlook limits how many emails you can send or forward in a day. When your account gets close to this limit, the system doesn't block your emails but instead slows them down by putting them in a queue. This can cause forwarded messages to be delayed by several hours or even up to a day.


Specific Issues with Forwarding OTPs from Multiple Accounts

When you forward emails from multiple Hotmail accounts to a single Gmail, especially for time-sensitive messages like One-Time Passwords (OTPs) from a single service, you introduce several points of failure that often lead to delays or messages not arriving at all.

This happens for a few key reasons. First, both Microsoft's and Google's systems may see a large number of similar emails coming from multiple accounts to one destination as spam-like behavior. This can trigger throttling, where the services deliberately slow down delivery to prevent abuse, causing significant delays. Second, forwarded emails often fail security checks, and since OTPs are high-security messages, Gmail is more likely to reject them or send them to its spam folder. Finally, the original OTP email might land in the Hotmail junk folder to begin with, and since forwarding rules typically only apply to the inbox, the email is never sent to your Gmail account in the first place.


Recommendations

Based on these issues, here are our recommendations for a more stable setup:

Avoid Unnecessary Logins: Since logging into a Hotmail account can trigger a security check that disables your forwarding rules, try to avoid logging in unless absolutely necessary. Let the forwarding rules work in the background and access your emails from the master account.

Limit and Distribute the Load: To avoid triggering spam filters and rate limits, do not forward too many Hotmail accounts to a single master Gmail account. It's better to split your batch of Hotmail accounts across several master Gmail accounts. This distribution makes the forwarding activity look less like a high-volume, automated process and reduces the risk of being flagged for throttling or spam.

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