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problems sending one email to multiple recipients

Just started having problems: I can't send one email to multiple recipients. When I tried to write an email and added 3 recipients - it comes up with the message that the address 'does not appear to be a valid email address' although I verified the correct email. After that, it tells me that 'the stmp did not recognize the following recipients'. The weird thing is that the email will send when just sent to individual recipients.

I haven't updated anything or done anything different. I can't figure it out. Any solutions?

Posted on Mar 24, 2022 7:21 AM

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Question marked as Top-ranking reply

Posted on Mar 24, 2022 8:37 AM

NathanTTu wrote:

Just started having problems: I can't send one email to multiple recipients. When I tried to write an email and added 3 recipients - it comes up with the message that the address 'does not appear to be a valid email address' although I verified the correct email. After that, it tells me that 'the stmp did not recognize the following recipients'. The weird thing is that the email will send when just sent to individual recipients.
I haven't updated anything or done anything different. I can't figure it out. Any solutions?


what changed...?



Monterey you can try turning off some of these new features and see if it makes a differnece:


Open mail app select Mail>Preferences>Privacy disable “Protect Mail Activity” / “Hide IP address” / “Block all remote content”


Use Mail Privacy Protection on Mac - Apple Support

Use Mail Privacy Protection on Mac - Apple Support



6 replies
Question marked as Top-ranking reply

Mar 24, 2022 8:37 AM in response to NathanTTu

NathanTTu wrote:

Just started having problems: I can't send one email to multiple recipients. When I tried to write an email and added 3 recipients - it comes up with the message that the address 'does not appear to be a valid email address' although I verified the correct email. After that, it tells me that 'the stmp did not recognize the following recipients'. The weird thing is that the email will send when just sent to individual recipients.
I haven't updated anything or done anything different. I can't figure it out. Any solutions?


what changed...?



Monterey you can try turning off some of these new features and see if it makes a differnece:


Open mail app select Mail>Preferences>Privacy disable “Protect Mail Activity” / “Hide IP address” / “Block all remote content”


Use Mail Privacy Protection on Mac - Apple Support

Use Mail Privacy Protection on Mac - Apple Support



Mar 24, 2022 5:45 PM in response to NathanTTu

NathanTTu wrote:
Maybe I updated to Monterey 12.0.1, since this is the version I have.

***UPDATE**** I wasn't able to figure out the problem, BUT it self corrected itself. I decided to do a test in the PM, and it worked. I can only assume that it was some issue with the company that hosts my websites in which my emails send through. I am just happy it is corrected. Unfortunately, I will be no help to others having a similar issue since I just got lucky with a self-correction.


Well, "try again later" —is always sage advice for glitches, one off's, server issue, etc before you pull the fire alarm...



I will add your post above " Monterey 12.0.1"— the current stable release of Monterey is macOS 12.3


Keep your Mac up to date - Apple Support

https://support.apple.com/guide/mac-help/get-macos-updates-mchlpx1065/mac



Mar 24, 2022 9:56 AM in response to leroydouglas

Thank you for taking the time to respond. Your suggestion didn't help. I can't think of anything that has changed. Maybe I updated to Monterey 12.0.1, since this is the version I have. I can't think of anything else. Again, the the weird thing is that the emails will send when just sent to one individual recipient.


Maybe something changed with my host server smtp since part of the error is saying: "The server 'smtp.****.com' rejected the address". I just tested sending the same email with the same two recipients, but using my iCloud server, and all worked fine.

I'll check with my smtp....


I'll keep you posted....

Mar 24, 2022 10:01 AM in response to BobTheFisherman

Thank you for taking the time to respond. I checked all email addresses and even typed them in manually as a test. The weird thing is that the emails will send when just sent to one individual recipient, but if I 'cc' another person or add another person to the 'TO', then it won't go through.


I mentioned to "leroydouglas", that I am checking with my host smtp server since part of the error is saying: "The server 'smtp.****.com' rejected the address". I just tested sending the same email with the same two recipients, but I used my iCloud server, and all worked fine.


I'll keep you posted....

Mar 24, 2022 5:23 PM in response to NathanTTu

***UPDATE**** I wasn't able to figure out the problem, BUT it self corrected itself. I decided to do a test in the PM, and it worked. I can only assume that it was some issue with the company that hosts my websites in which my emails send through. I am just happy it is corrected. Unfortunately, I will be no help to others having a similar issue since I just got lucky with a self-correction.

problems sending one email to multiple recipients

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