I have two SMTP servers configured in Mail. One for school, and one for my private email. I would like that Mail automatically picks the one for school if I'm sending an email to someone of my school. This means: any email address of someone of my university ends in @ugent.be. So if I write an email to xyz@ugent.be, I want mail to pick my UGent SMTP server. In all other cases, I want to use my gmail SMTP server configuration. Is this possible? If not, are there any applications that support this feature? (Some people on the university are very strict and won't reply unless you sent the email from your university email address. And I like it separated nicely as well.)

Mail program 16.0, on Sequoia 15.5, 16" Mac Book Pro Apple chip M3 Max I have emails that come to my Mac Mail program via @iCloud.com email account. I also have in the same mail app a few Gmail imap accounts. Sometimes id like to forward an @iCloud.com email to a person using a gmail account - which im told by apple tech support im suppose to be able to do & have done previously with no issues - until lately. Not sure when the problem started. I'll select the @iCloud.com email to forward, click forward, change the " from account " to a gmail account, compose and send the email. The problem is that the emails are not sent using the selected gmail account , but are being sent by apple mail and is using my Apple ID - which I do not want to be used or made public. Id like the email to be forwarded using the selected gmail account. How can I figure out what causing this unexpected behavior & how can I make the forwarded emails be sent from the selected gmail account and not my Apple ID account? To add to the frustration & curiosity, when I try the above send procedure using apple mail & forwarding with gmail , it works as expected on all my iOS devices - iPhone & iPad. Ive checked the gmail accounts on my MacBook Pro to make sure the smtp's are correct and they all show gmail credentials. Ive also removed & re-added the gmail accounts with no change in behavior. I dont know what else to try / check. Help appreciated. Attached is a screen shot of the drop down menu I use to select gmail account when composing the forwarding email. Thank you.

Right so we have set up a mail server for our company that does not use imap nor pop at the moment, it is based on PEPS open source and only communicates via https and smtp port 25. I can't figure out how to link it with my mail client to read my email as it always asks for imap or pop :/ What are my options?

I am using msmtp as a mail client on an M1 iMac still running Monterey. I use Gmail as a relay. It's been working fine, except recently I started getting the following error message:

send-mail: TLS certificate verification failed: the certificate fingerprint does not match

So, I generate a new fingerprint with this:

msmtp --serverinfo --tls --tls-certcheck=off --host=smtp.gmail.com --port=587 | egrep -o "([0-9A-Za-z]{2}:){31}[0-9A-Za-z]{2}"

And then it works, until it doesn't. In the last couple of days I've had to generate three new fingerprints. Why do the fingerprints seem to expire and is there anything I can do about it?

In Mail.app I have several mail addresses and incoming mail to some addresses is already being forwarded to my primary mail address. I don't want to have an inbox for these secondary emails (I've got them on my primary anyway) but I want to be able to send from those addresses. I've tried adding my secondary account as usual, and then disabling it. But then I can't see that address' SMTP server to send from when sending. If I enable it, I can see it, but its mailbox automatically comes back. How can I have no mailbox for a mail account, but still be able to select its SMTP server to send mail from that address?

I forward my university email address to my GMail account, so I don’t have my university IMAP set up as an account on my iPad (and I don’t want to, because then I’d receive those mails twice). Still, I want to send email using that address, via my university’s SMTP server. * Is there any way to add another sender address to an account and assign it a different SMTP server than the account’s default SMTP in the iPad’s email client? * If not, can you recommend another email client for the iPad that has this capability?

Today I noticed I have 3 emails stuck in my Outbox, and when I try to re-send one, I see: If I press **Settings**, then select "SMTP Gmail SMTP Server", and "Gmail SMTP Server" (under PRIMARY SERVER--it is the only one shown as "On"), I see: I can't edit anything here. Has Gmail changed the way their SMTP authentication works? How do I fix this?

I've set up the Mail component in the Server.app to provide an internal mail server. We used to use this mail server to send mail (via SMTP) without TLS on port 25 which worked well enough. Now I wanted to secure SMTP with either SSL/TLS , but I cannot get it to work. This is what I did: - In the Server.app, under *Certificates*, I've assigned an SSL certificate to the service *Mail (SMTP)* as well as to *Mail (IMAP and POP)* - I've tried to send mail via SMTP with SSL on ports 25, 587, and 465, which all failed. - I've tried to send mail via SMTP with StartTLS on the same port, which succeeded on port 25 and 587. - I've tried to send mail without any secure channel, which succeeded on port 25 and 587. My conclusions are - port 465 is not available - ports 25 and 587 respond identically - StartTLS works, and it's using the configured certificate - SSL does not work Trying to verify SSL with openssl gives me the following error

`
$ openssl s_client -showcerts -connect smtp.mail.localdomain:25 -servername smtp.mail.localdomain 
CONNECTED(00000005)
4306470444:error:1400410B:SSL routines:CONNECT_CR_SRVR_HELLO:wrong version number:/AppleInternal/Library/BuildRoots/a0876c02-1788-11ed-b9c4-96898e02b808/Library/Caches/com.apple.xbs/Sources/libressl/libressl-2.8/ssl/ssl_pkt.c:386:
---
no peer certificate available
---
No client certificate CA names sent
---
SSL handshake has read 5 bytes and written 0 bytes
---
New, (NONE), Cipher is (NONE)
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
SSL-Session:
    Protocol  : TLSv1.2
    Cipher    : 0000
    Session-ID: 
    Session-ID-ctx: 
    Master-Key: 
    Start Time: 1663316761
    Timeout   : 7200 (sec)
    Verify return code: 0 (ok)
---

` Verifying StartTLS with openssl shows that it indeed works. Why does connecting over SSL/TLS not work? What am I missing here?

I recently installed both msmtp (smtp client) and mailutils on an M1 iMac via MacPorts. I couldn't get msmtp to work until I realized that there were two mail binaries on the machine, one that, I guess, is native and one installed by mailutils:

Valentine:~ mnewman$ which -a mail
/opt/local/bin/mail
/usr/bin/mail

Unfortunately, the wrong one was being used if I tried to send mail from the Command line which caused msmtp to fail. I tried to fix it with:

Valentine:~ mnewman$ alias mail="/usr/bin/mail"
Valentine:~ mnewman$ type mail
mail is aliased to `/usr/bin/mail'

Which works, but I think there must be a better way. Is there? Edited to show why I need to use /usr/bin/mail rather than /opt/local/bin/mail with msmtp:

Valentine:~ mnewman$ /opt/local/bin/mail me@mac.com
Cc:
Subject: none
test
msmtp: no recipients found
Sending data to /opt/local/bin/msmtp failed: Process exited with a non-zero status
cannot send message: Process exited with a non-zero status
Valentine:~ mnewman$ /usr/bin/mail me@mac.com
Subject: none
test
EOT

/opt/local/bin/mail fails while /usr/bin/mail works

Question about macOS Mail, under Monterey: I want to backup the list of outgoing servers, which has some obscure problems. After an extensive search (at least it seemed extensive), I can't find the plist file that contains the list. Does anyone know where to find it? Many thanks for any help.

On a brand new Macbook running Monterey (M1), as PHP was removed by Apple on OS 12, I have removed all "AMP" preinstalled by Apple and installed HomeBrew "AMP" (with PHP 7.4), which is running perfectly. Now, as I have setup Wordpress for testing purposes, I am attempting to use Wordpress WP_Mail function, which relies on PHPMailer, which in turn uses PHP Mail command. The latter relies on system specific libraries, and I am bit confused about configuring the correct facility, Mail, SendMail, Mailsend.... Digging the Internet, once upon a time you would achieve this through Postfix or eventually setting up an email account in the System settings for Mail.app , which I would like to avoid, as I only use web mail on browser and hate to have an email client accessing my account......... In conclusion, on a Monterey M1 machine, Homebrew "AMP" scenario, is there a way to allow PHPMailer to work, avoiding using Mail.app account?

Lion Mail Server component postfix/smtp 100% reproducible blocks inbound smtp mail delivery on first boot after a panic or power failure. Error messages from mail.log are like: postfix/smtp: connect to 127.0.0.1[127.0.0.1]:10024: Connection refused postfix/smtp: 2F7131F9A97: to=, relay=none, delay=76041, delays=76040/0.36/0.05/0, dsn=4.4.1, status=deferred (connect to 127.0.0.1[127.0.0.1]:10024: Connection refused) postfix/error: 550D61F9A99: to=, relay=none, delay=76040, delays=76040/0.39/0/0, dsn=4.4.1, status=deferred (delivery temporarily suspended: connect to 127.0.0.1[127.0.0.1]:10024: Connection refused) postfix/postscreen: NOQUEUE: reject: RCPT from [100.200.100.159]:65392: 450 4.3.2 Service currently unavailable; from=, to=, proto=ESMTP, helo= /usr/libexec/postfix/greylist.pl: Temporary message rejection to: from: sent from: [100.200.100.159] for: 60 seconds due to greylisting postfix/smtpd: NOQUEUE: reject: RCPT from host.domain.tld[100.200.100.159]: 450 4.7.1 : Recipient address rejected: Service is unavailable; from= to= proto=ESMTP helo= The issue seems to be related to the **amavis** content filter due to the connection to port number 10024 and amavisd being configured on that port. Amavis.log: /usr/bin/amavisd: (!)Net::Server: 2012/07/25-13:38:49 Pid_file already exists for running process (88)... aborting\n\n at line 277 in file /System/Library/Perl/Extras/5.12/Net/Server.pm ... /usr/bin/amavisd: Net::Server: 2012/07/25-13:38:49 Server closing! ...repeating roughly every 10 seconds... The **workaround** is to delete /var/amavis/amavisd.pid or reboot the machine. After the second boot the inbound smtp mail delivery is no longer stuck. The issue seems to be **related to** https://serverfault.com/questions/138690/amavisd-net-server-pid-file-already-exists-after-system-crash-and-startup **How to permanently fix** Apple Mail Server to accept smtp inbound messages on first boot, by removing the left over amavis pid_file from the previous unclean shutdown?

Recently I noticed that on both Spark and the default mail app, my name is being replaced as "Holiday In The United States". This is happening on all my accounts, with various email providers. I have verified my name in both System Preferences, Spark Preferences, and Mail Preferences. Additionally, I have checked my name on each email provider's settings. To clarify, I am only seeing my name as "Holiday In The United States" from my Mac, not online. Any way I can fix this? It is really annoying having to log-in from the browser to send mail. I am currently on a MacBook Pro Mid 2014, running Mac OS Sierra 10.12.3.

When I'm in Accounts and I select the dropdown of SMTP servers I get a long list of servers (as I manage a lot of accounts). But when I go to edit the SMTP server list, not all of the accounts in the dropdown are listed. Any ideas what's happening?

macOS Mail won't clear out the outgoing SMTP server list PLEASE NOTE three symptoms in one that makes this extremely buggy: 1) - going to "Edit SMTP server list..." and then deleting the items from the list window DOES NOT WORK 2) - when I try to add new SMTP servers, my new server does not "stick" and is not choosable (and has no effect) 3) - when I edit an existing one, any changes I make appear to stick only until I quit & relaunch Mail, after which Mail appears to REVERT to the old settings for my SMTP server list. this has always been buggy (over the last 20 years), but only under Catalina 10.15.7 is this now no longer editable for me

I'm out of ideas on what to try here. 2018 MBP running Mojave 10.14.6. I just received a new work email address, that was just created and has never been used before. I have numerous other email addresses on this machine including Gmail, iCloud (me.com), and personal domains that all work perfectly well using IMAP/SMTP. This address just refuses to authenticate. The password is correct, everything is correct and in fact works perfectly at the host's webmail portal (hosts.co.uk). Specifically in Connection Doctor I get: WROTE Jan 15 17:42:49.136 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:imap.hosts.co.uk -- port:143 -- socket:0x600002192100 -- thread:0x6000050c7a00 8.1138 LOGIN my_login_id ******** READ Jan 15 17:42:59.137 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:imap.hosts.co.uk -- port:143 -- socket:0x600002192100 -- thread:0x6000050c7a00 8.1138 NO [AUTHENTICATIONFAILED] Authentication failed. WROTE Jan 15 17:42:59.137 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:imap.hosts.co.uk -- port:143 -- socket:0x600002192100 -- thread:0x6000050c7a00 9.1138 LOGOUT I've tried everything I can think of including manual (Advanced) settings for port, different SMTP account selections, enabling "less secure apps" on Google (since I'd like to use them for SMTP), confirming Google's "I'm really me" CAPTCHA, and a host of other stuff I can't even remember at this moment. This is my only address that fails to work, and in fact the only address I've ever had not "just work" and I've been using Mail since the beginning. Any suggestions?

I have tried everything (I guess), such as writing my sasl_passwd and editing main.cf in the /etc/postfix folder (as described in [1] ). I also copied my LaunchDaemon plist with a different name to my /Library/LaunchDaemons folder (as described in [2] ). While those people managed to get postfix to send smtp Gmail messages from their terminal under Mojave and El Capitan, respectively. I haven't managed to get their solutions to work under Catalina. Any suggestions?

I'm trying to use applescript to do two things: 1. Create an account in Mail.app 2. Using that account, send an email in Mail.app I'm having an issue with creating an account on Mail.app mainly because theres no "SMTP server", and I'm trying to use Yahoo. No matter what I try, I can't get Applescript to automatically add yahoo as the smtp outgoing server. Here's my code: tell application "Mail" set AccountName to "account_name" set newacct to make new pop account with properties {name:AccountName, user name:"account_name@yahoo.com", server name:"mail.yahoo.com"} tell newacct set password to "ThePassword" set full name to AccountName set email addresses to {"account_name@yahoo.com"} set port to 995 set uses ssl to true end tell set addsmtp to make new smtp server with properties {server name:"smtp.mail.yahoo.com", user name:"account_name@yahoo.com"} tell addsmtp set password to "ThePassword" set uses ssl to true set port to 465 end tell set smtp server of newacct to addsmtp end tell

I have two accounts set up in Apple Mail. The second account is for backup purposes and because at times the primary account is unavailable. When that happens, I send from the second account but would like the reply-to address to be that of the primary account. Is there a way to set things up this way in Apple Mail?

I recently updated my Mac Pro from Sierra to High Sierra and now Mail cannot connect to the Gmail SMTP server. So I can receive mail but I cannot send. I have found posts from many other users with the same problem and none of the solutions have worked for me. I have tried deleting prefs, deleting my Gmail account in Internet Accounts, turning on and off two step verification, and nothing has worked. When I run Connection Doctor, I see the following in the error log: WROTE Mar 07 10:32:09.713 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:465 -- socket:0x6140004a3060 -- thread:0x600000267340 EHLO vuze on mac-pro.home READ Mar 07 10:32:09.749 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:465 -- socket:0x6140004a3060 -- thread:0x600000267340 501-5.5.4 HELO/EHLO argument "vuze on mac-pro.home" invalid, closing Oddly, when I open terminal the command prompt says "vuze on Mac-Pro:". So this makes me think the problem is something OS or network related, but I have no idea where to start. Any ideas?