Suddenly Apple Mail is blocking email sent to myself/my email address

For years I could always send email to myself, and / or bcc myself, and /or bcc myself to same address. Now suddenly when I send email to my own email address, Apple Mail bounces it back as undeliverable with this message:

Remote Server returned '550 5.7.520 Message blocked because it contains content identified as spam. AS(4810)'


Please can anyone help me fix this?


Thank you!

PS Contacted Microsoft outlook.com Support and they report that this is an Apple issue, not Microsoft.


iPhone SE

Posted on Jul 18, 2021 11:23 AM

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Posted on Aug 4, 2021 11:40 PM

Hi cb1946


I've recently experienced this myself, and it appears to have been due to a VPN app on my phone. Whenever I used the app, Microsoft account team would send me an email advising of unusual sign-in activity, which I promptly deleted. It appears that after several ignored emails, they blocked outgoing emails from my iPhone.


I located one of the deleted "Verify your account" requests in my Trash and followed the links, after logging in I was presented with a list of suspicious activities which I confirmed as being legitimate. Now I can send emails again.


I hope this helps. Good luck!

24 replies
Question marked as Top-ranking reply

Aug 4, 2021 11:40 PM in response to cb1946

Hi cb1946


I've recently experienced this myself, and it appears to have been due to a VPN app on my phone. Whenever I used the app, Microsoft account team would send me an email advising of unusual sign-in activity, which I promptly deleted. It appears that after several ignored emails, they blocked outgoing emails from my iPhone.


I located one of the deleted "Verify your account" requests in my Trash and followed the links, after logging in I was presented with a list of suspicious activities which I confirmed as being legitimate. Now I can send emails again.


I hope this helps. Good luck!

Jul 18, 2021 11:32 AM in response to cb1946

It would appear that your arriving mail message (this doesn’t seem to be a local bcc; I’d not expect a 550 from local) is being detected as spam, or is spam, or the sending email server is shipping a lot of spam and your message got caught in the barrage.


Whitelist your sending email account by adding it into your list of contacts in iCloud, if that is not already in place.


Contact Apple iCloud support.


Jul 18, 2021 7:09 PM in response to cb1946

Microsoft is likely using the connecting IP address as input data into their spam filtering algorithm.

This is part of why I suggested an IP router reset, as a reset can sometimes acquire a different IP address.

The router reset can also clear up the connection messes that some routers can get themselves into.

Free mail providers are unlikely to invest heavily providing support for their non-paying users, too.

But again, 550, from mail sent to a Microsoft server by a Microsoft subscriber, is a Microsoft issue for Microsoft to address.



Jul 18, 2021 2:41 PM in response to cb1946

If the SMTP 550 is from a Microsoft msn-related mail server (and not some other mail server), then SMTP 550 from an arriving not-via-TCP-port-25 connection with valid credentials and settings from a subscriber implies Microsoft has a mail server or spam-filtering issue, then.


Best I can suggest is testing with a different mail client, as a means to convince Microsoft of the location of the error.


But a 550 should be an obvious location, as it's the SMTP server that generated the 550 that didn't like whatever it saw from a subscriber and bounced it.

Jul 18, 2021 8:13 PM in response to MrHoffman

Thanks so much Mr. Hoffmann I really appreciate all your expertise, helpful responses and explanations, and al your info. I’m so frustrated, I better give up and not hold my breath for help or resolution from Microsoft to resolve it.

Hassle: From now on whenever I want to bc or cc myself on an email or send an email to myself, I will have to remember to go into settings, turn my wifi off, use cellular data, and then send the email. WHAT A HASSLE!

Jul 18, 2021 12:14 PM in response to MrHoffman

Thank you Mr. Hoffman, I appreciate your response. Forgive my ignorance, but can you tell me how to do that? I don’t even use iCloud (except for what Apple does automatically).

I’m also going back to my Microsoft Support case number/ticket (they just said contact Apple it’s Apple problem) because my email account address is an msn account, and something must be amiss with the email server — which is what you say too!

Jul 18, 2021 12:31 PM in response to MrHoffman

BTW Mr. Hoffman your response makes sense (email getting caught up in a bunch of spam (not mine)) to my non technical brain (legal brain and logic brain but not techie brain!) because this is weird: If I turn off WIFI, and use cellular, a message to myself will send ok maybe once or twice, but not with WIFI on. This is crazy. And it just started few days ago. Never in years had this problem. SO FRUSTRATED!

I appreciate your help. I’m determined to fix this!!!

Jul 18, 2021 1:04 PM in response to MrHoffman

Thanks! I really appreciate ALL your info and time and heIp and surprise I actually DO understand that babble. Because having an msn email account for a zillion years, and long go on my original very first they ever made iPhone (2007 the FIRST ONE) it was not easy to get msn email. So over the years I’ve learned about POP an IMAP accounts, etc. But that’s all history. Apple iPhones and iPads make it easy to set up an “other” email account. When I added it to the ipad few years ago, the Apple techies were amazed at my info I brought in. But I had learned through the years about making sure email account is set up with exact proper configurations.

Be that as it may, twice I did delete the account and re add it, hoping praying that would fix it!, but nope sadly it did not.


I wish I didn’t have the legal analysis to sawdust brain that makes me determined to resolve this. Something happened out of my control or doing the other day, others are also having problem, some relief that it’s not just me.



Jul 19, 2021 1:24 AM in response to cb1946

From Microsoft, another unhelpful frustrating form (paragraphs are always the same) response. He’s missing the entire 550 SPAM error message filtering Issue.

“Thank you for responding back.  


We appreciate your patience throughout the conversation.


If I were in your position, I would feel the same way. 


We appreciate your efforts in sharing with us further update on the issue as requested.


As you have confirmed that when you send test email to self then you receive it when using different Wi-Fi address however when you send test email to self-using own home Wi-Fi then you get the error message so it is evident that issue is with internet so contact you internet service provider to fix your home Wi-Fi issue.


Again, we appreciate your patience, efforts and cooperation on this matter. I hope everything goes well. 


Stay healthy and stay safe.


Have a great day!”


And Netgear tech support guaranteed a call back to me 6 hours ago. Never called.


ughhhhhhhh......

Jul 19, 2021 10:11 AM in response to MrHoffman

Thank you very much. I really appreciate your information and help with options.

Microsoft Support escalates the ticket/case/issue to a level 2 (?).

This 550 error block will sometime “age out”? Hope springs eternal!

I thought of changing my IP address, but yikes I don’t want to cause more problems.

I’d gladly pay for email if I could keep my same email address.

Aug 5, 2021 2:51 AM in response to samjandrewz

Add-on commercial VPNs are a wonderful way to have your network traffic centralized, tracked, logged, packaged, and presumably then resold.


VPNs get massively advertised because access to your network traffic is profitable.


That, and give. the resulting VPN uses widely-known credentials, the added “security” provided is weak at best.


I would wonder if some of the services use added trusted certificates to intercept and decrypt and scan SSL/TLS traffic, too. Which would explain some of the network connection issues reported around various forums.


Outside of geolocation shifting for testing, I’d suggest avoiding all that. If you need local connection protection past SSL/TLS, consider using Algo or Streisand and your own connection.

Aug 17, 2021 8:03 AM in response to cb1946

cb1946 - was this ever resolved ? I now have the same issue which seems to have coincided with changing my hotmail password. It is definitely an Apple issue as I can send to my own hotmail account via Outlook and Sky. My password has been changed for all my settings and I am at a loss why this has suddenly started to happen.


Regards


Peter

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