issues with send mail pop-up

I'm using MAC OS 12.6.2 and "MAIL" Version 16.0 (3696.120.41.1.1) on a MacBook Pro (Retina, 13-inch, Early 2015)


Within "MAIL" I have connections set up to gmail, yahoo mail, and my website email server and "MAIL" download email and sends email from those servers. This has been stable for many years.


When I send an email, I have to select in the Drop-down which email address I wish to use for gmail, yahoo mail, or my website email server for each email sent.


Now when I wish to send an email by gmail a NEW subsequent Pop-Up has stated appearing asking to select the server to use, so I chose gmail in that case and the mail is sent without issues with the gmail address.


However, when I select from the drop-down in an email I wish to send my website email address the mail goes without the Pop-Up window showing which server to use, so I can't alter.


The result is that email I wanted to send from my website email address I selected from the dropdown within that email that particular email is sent without the pop-up showing.


The issue is that email on receipt shows as beings sent from gmail, which is causing issues.


My website email preferences for Incoming and Outgoing host servers are listed as the website server and have worked well up to now.


Is there anyway to ensure an email being sent using my website address uses that address, which I have selected in 'MAIL".






Posted on Jan 18, 2023 11:54 AM

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5 replies

Jan 19, 2023 7:16 PM in response to Memoire

Hello Memoire,


Thank you for reaching out in Apple Support Communities. We understand you're unable to send an email from a specific email address you have. For this issue, we suggest to follow these steps as it can help resolve your issue:


"If you can’t send emails in Mail on Mac

In the Mail app  on your Mac, if the Send button  is dimmed in the toolbar of your message, or your message can’t be sent using the outgoing Mail server, try these suggestions.


  • Make sure the outgoing (SMTP) mail server is specified as directed by the provider of your email account. See Verify an email account’s outgoing server.
  • Choose Window > Connection Doctor, then follow the instructions displayed in the Details column.
  • If there’s a firewall problem, verify that firewall software isn’t blocking email traffic on port 25, 465, or 587. Also check whether you’re affected by another firewall, such as software installed separately from macOS or built into an internet sharing router, or administered by your email account provider. Contact the appropriate person for information.


You may be able to send messages from only a certain location, or your email account provider may have stricter settings for sending messages (such as requiring a name and password). Contact your provider, then change the outgoing mail server settings in Mail settings as needed."


Following these steps may help and is outlined in this helpful article: If you can’t send emails in Mail on Mac - Apple Support


Best regards.

Jan 21, 2023 3:20 AM in response to bryanr14

Hi bryanr14

Thank you for your reply, time and support, much appreciated.


I have had no issues sending emails as such. Just that the email being sent by the selected server of my website email address in the dropdown of the email to be sent is subsequently received with the Gmail address.


My own website email address will be sent as the Gmail address if I have previously to that sent a mail using the Gmail server in the dropdown on the email to be sent.


There was no issue until recently, I assume the only likely event was the recent security update, 12.6.2 - only a guess.


I already checked the outgoing (SMTP) mail server specified for all addresses as directed by the provider of the email account before raising this issue in the community.


Google data only shows "Google" and no other data as usual.


While other email addresses show:



All the addresses shown in the Mail Connection Doctor "Connection and Login to server succeeded".


I have 6 email addresses set up in Mail, it appears only Gmail is causing issues.


At a loss how to guarantee that emails sent from my Website email address don't show the Gmail email address when received, even though my Website email address/server is selected in the email dropdown before being sent.


Any ideas would be most welcome.



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issues with send mail pop-up

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