Making aol.smtp.com work with Mac Apple Mail

edwilliams16 · 2026-09-17T18:15:00+00:00

I have been trying in vain to get my Mac Apple Mail to send mail from my aol account. IMAP receive always works. The smtp settings I'm using together with the specific app password work with Mac Thunderbird and with Apple Mail on my Ipad. Connection doctor reports successful connection to the smpt server, but the email request is rejected. I've tried both possible port numbers. I've removed the AOL account and re-created it afresh with no change in behavior. Every time "The server response was: Request failed; Mailbox unavailable" Is this hopeless or is there a solution?

BobTheFisherman

Level 10 (87,747 points)

Sep 17, 2026 6:20 PM in response to edwilliams16

It is not surprising that aol.smtp.com is not working.

Here is the outgoing configuration for an aol email account. Try these settings:

SMTP Server: smtp.aol.com

Port: 587 (with TLS/STARTTLS) or 465 (with SSL)

Username: Your full AOL email address

Password: Your regular AOL account password or an app password (if 2-step verification is active)

Authentication: Required / Enabled

Required Encryption: SSL or TLS

edwilliams16 Author

Level 1 (4 points)

Sep 17, 2026 6:46 PM in response to BobTheFisherman

My bad a typo. Of course I was actually using smtp.aol.com. Otherwise connection doctor would have failed.

In Apple mail and the other apps which work I was using the settings you list above.

I tried both 587 and 465 with Use TLS/SSL checked, as the checkbox is somewhat ambiguous.

edwilliams16 Author

Level 1 (4 points)

Sep 17, 2026 8:34 PM in response to edwilliams16

Here's the anonymized log file from the connection doctor. it logs in, is authenticated, but chokes at the last second...

INITIATING CONNECTION Sep 17 16:48:00.940 host:smtp.aol.com -- port:587 -- socket:0x0 -- thread:0x600001474a00

CONNECTED Sep 17 16:48:01.045 [kCFStreamSocketSecurityLevelNone] -- host:smtp.aol.com -- port:587 -- socket:0x6000065fdd40 -- thread:0x600001474a00

READ Sep 17 16:48:01.133 [kCFStreamSocketSecurityLevelNone] -- host:smtp.aol.com -- port:587 -- socket:0x6000065fdd40 -- thread:0x600001474a00

220 smtp.mail.yahoo.com ESMTP ready

WROTE Sep 17 16:48:01.133 [kCFStreamSocketSecurityLevelNone] -- host:smtp.aol.com -- port:587 -- socket:0x6000065fdd40 -- thread:0x600001474a00

EHLO smtpclient.apple

READ Sep 17 16:48:01.223 [kCFStreamSocketSecurityLevelNone] -- host:smtp.aol.com -- port:587 -- socket:0x6000065fdd40 -- thread:0x600001474a00

250-hermes--production-gq1-678d9dd684-6hkng Hello smtpclient.apple [72.234.40.27])

250-PIPELINING

250-ENHANCEDSTATUSCODES

250-8BITMIME

250-SIZE 41697280

250 STARTTLS

WROTE Sep 17 16:48:01.223 [kCFStreamSocketSecurityLevelNone] -- host:smtp.aol.com -- port:587 -- socket:0x6000065fdd40 -- thread:0x600001474a00

STARTTLS

READ Sep 17 16:48:01.312 [kCFStreamSocketSecurityLevelNone] -- host:smtp.aol.com -- port:587 -- socket:0x6000065fdd40 -- thread:0x600001474a00

220 2.0.0 Ready to start TLS

WROTE Sep 17 16:48:01.650 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.aol.com -- port:587 -- socket:0x6000065fdd40 -- thread:0x600001474a00

EHLO smtpclient.apple

READ Sep 17 16:48:01.737 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.aol.com -- port:587 -- socket:0x6000065fdd40 -- thread:0x600001474a00

250-hermes--production-gq1-678d9dd684-6hkng Hello smtpclient.apple [72.234.40.27])

250-PIPELINING

250-ENHANCEDSTATUSCODES

250-8BITMIME

250-SIZE 41697280

250 AUTH PLAIN LOGIN XOAUTH2 OAUTHBEARER

WROTE Sep 17 16:48:01.737 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.aol.com -- port:587 -- socket:0x6000065fdd40 -- thread:0x600001474a00

AUTH PLAIN (*** 96 bytes hidden ***)

READ Sep 17 16:48:02.749 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.aol.com -- port:587 -- socket:0x6000065fdd40 -- thread:0x600001474a00

235 2.7.0 Authentication successful

WROTE Sep 17 16:48:02.749 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.aol.com -- port:587 -- socket:0x6000065fdd40 -- thread:0x600001474a00

MAIL FROM:<[email protected]>

READ Sep 17 16:48:02.923 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.aol.com -- port:587 -- socket:0x6000065fdd40 -- thread:0x600001474a00

250 2.1.0 Sender <[email protected]> OK

WROTE Sep 17 16:48:02.924 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.aol.com -- port:587 -- socket:0x6000065fdd40 -- thread:0x600001474a00

RCPT TO:<[email protected]>

READ Sep 17 16:48:03.012 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.aol.com -- port:587 -- socket:0x6000065fdd40 -- thread:0x600001474a00

250 2.1.5 Recipient <[email protected]> OK

WROTE Sep 17 16:48:03.012 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.aol.com -- port:587 -- socket:0x6000065fdd40 -- thread:0x600001474a00

DATA

READ Sep 17 16:48:03.099 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.aol.com -- port:587 -- socket:0x6000065fdd40 -- thread:0x600001474a00

354 Ok Send data ending with <CRLF>.<CRLF>

WROTE Sep 17 16:48:03.100 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.aol.com -- port:587 -- socket:0x6000065fdd40 -- thread:0x600001474a00

From: Ed <[email protected]>

Content-Type: text/plain

Content-Transfer-Encoding: 7bit

Reply-To: [email protected]

Mime-Version: 1.0 (Mac OS X Mail 16.0 \(3826.700.81.1.6\))

Subject: Test from compuserve.

Message-Id: <[email protected]>

Date: Thu, 17 Sep 2026 16:47:50 -1000

To: Ed <[email protected]>

X-Mailer: Apple Mail (2.3826.700.81.1.6)

.

READ Sep 17 16:48:03.192 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.aol.com -- port:587 -- socket:0x6000065fdd40 -- thread:0x600001474a00

550 Request failed; Mailbox unavailable

WROTE Sep 17 16:48:03.192 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.aol.com -- port:587 -- socket:0x6000065fdd40 -- thread:0x600001474a00

QUIT

As I understand it, the 550 error is with the recipient mailbox - but if so why can I send to it with other clients? I can't send to any recipients.

Making aol.smtp.com work with Mac Apple Mail

3 replies