Why is email between Hotmail accounts lost?

To be completely honest, I’m not sure you can resolve it.

I’ve been getting more and more reports of email being lost – simply not being
received – by Hotmail accounts.

And while I haven’t seen any patterns, I’ll speculate some on possible
causes.

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The symptoms are pretty simple: two email accounts, one or both on Hotmail, that are apparently working just fine, except that email from one is never received by the other. The message sent looks like it worked: there’s no bounce, no warning, no error – but also no delivery to the recipient. The message is simply lost.

And it’s consistent when email is sent from the one account to the other.

Though the reverse isn’t typically true. Email from account “A” to account “B” may disappear, but email from “B” to “A” arrives normally.

And email from other sources arrives normally.

It’s actually quite frustrating.

I don’t have a specific cause, but I do have some ideas – some of which you can check.

• Hotmail does have a “blocked senders” list. If an email address appears on that list, it’s immediately deleted, resulting in the exact symptoms you’re experiencing. Click on Options (in the upper right), More Options, “Safe and blocked senders” and then “Blocked senders“. Check the list on the right carefully for the email address of the person who’s email you’re missing, and for the domain (“@domain.com” in the list will block all email addresses ending in @domain.com).

• Check your junk mail folder. In the common scenario that I’m talking about, the messages do not appear in the junk mail folder, but it’s important to check anyway. In particular, if you accidentally or on purpose click on the “Junk” button to delete an email, then you’re telling Hotmail that all email from that particular email address is likely to be junk. At some point Hotmail may start throwing email from that person directly into the Junk folder.

• Spam “from spoofing” can cause someone’s email address to be erroneously labeled as spam, or worse. In these scenarios spammers make email look like they’re coming from a particular email address, when they’re not. As individuals receive those emails and mark them as spam Hotmail can take note and mark legitimate emails from that address that weren’t spoofed as spam.

• Spam doesn’t seem to always land in the Junk folder. We’d like to assume that we always have the Junk folder to fall back on for anything that was sent to us, but it appears that not all email that is filtered as spam will in fact be placed there. I’d guess that if the email matches criteria that label it “bad enough”, the email is simply deleted. Those criteria might include content, the From: address, or other characteristics like the IP address from which it was sent.

Regardless of how it happens, the real question is what to do about it.

Unfortunately – aside from checking the blocked senders list as mentioned above – I have no ideas.

The problem may also disappear on its own. Or not.

The real issue here, I believe, is simply the war on spam. As spam fighting techniques evolve situations like this come up. Hopefully the fact that these techniques might be throwing false positives will eventually be detected and corrected, it’s not something that I’d rely on, or rely on happening quickly.

If this becomes a serious enough problem the only solution I know of that’s in your control is to use a different email account, either to send from, or to send to.