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OS X El Capitain SMTP Mail connection

Shai's Avatar

Shai

01 Nov, 2015 10:51 PM

After installing GPG_Mail, I cannot seem to get the SMTP server to connect. So running Connection Doctor yields that all my IMAP connections are fine, but the SMTP connection fail authentication. I switched from port 587 to 25, to no avail. I even turned off the SSL required connection, also to no avail. and checked my Firewall/Router - which nothing changed and work fine.
I can send mail from my Windows machine fine, running Win10 - same email setup. Also mail send fine from iPhone and iPad via WiFi router. Not sure what the issue is in this hangup. I also turned off the checks next to all composing - so it does not automatically encrypt and sign every mail. Still no connection.

Any advice is appreciated.

Replace this line here with Tool-Name: GPGMail, version 2.6b2, Build: 1105b
MacBook Pro, OS X El Capitain version 10.11.1
Mac Mail version 9.1 (3096.5)
Mailbox
Email: red [email blocked]
imap-mail.outlook.com
TLS certificate - none
Port 993, use SSL - checked
Authentication - password
SMTP Server - Port 25, Use SSL - checked
Authentication - password

Describe your problem. Add as much detail as possible.

The following is the log output for the error connection attempt to the SMTP server via Connection Doctor:

Nov 1 16:44:48 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 587, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 16:45:48 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 25, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 16:46:48 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 465, security layer: kCFStreamSocketSecurityLevelTLSv1 (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 16:47:48 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 587, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 16:48:01 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 587, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 16:48:48 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 25, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 16:49:01 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 25, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 16:49:48 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 465, security layer: kCFStreamSocketSecurityLevelTLSv1 (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 16:50:01 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 465, security layer: kCFStreamSocketSecurityLevelTLSv1 (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 16:53:02 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 587, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 16:54:02 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 25, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 16:55:02 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 465, security layer: kCFStreamSocketSecurityLevelTLSv1 (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 16:56:34 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 587, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 16:57:34 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 25, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 16:58:34 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 465, security layer: kCFStreamSocketSecurityLevelTLSv1 (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:00:57 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 587, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:01:57 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 25, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:02:57 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 465, security layer: kCFStreamSocketSecurityLevelTLSv1 (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:06:00 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 587, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:07:00 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 25, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:08:00 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 465, security layer: kCFStreamSocketSecurityLevelTLSv1 (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:11:44 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 25, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:11:44 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 25, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:12:44 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 587, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:12:44 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 587, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:13:44 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 465, security layer: kCFStreamSocketSecurityLevelTLSv1 (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:13:44 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 465, security layer: kCFStreamSocketSecurityLevelTLSv1 (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:14:45 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 25, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:15:45 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 587, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:16:45 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 465, security layer: kCFStreamSocketSecurityLevelTLSv1 (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:21:36 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 25, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:21:36 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 25, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:22:36 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 587, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:22:36 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 587, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:23:36 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 465, security layer: kCFStreamSocketSecurityLevelTLSv1 (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:23:36 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 465, security layer: kCFStreamSocketSecurityLevelTLSv1 (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:26:02 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 25, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:26:02 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 25, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:27:02 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 587, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:27:02 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 587, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:28:02 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 465, security layer: kCFStreamSocketSecurityLevelTLSv1 (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:28:02 Mail[284] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 465, security layer: kCFStreamSocketSecurityLevelTLSv1 (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out") Nov 1 17:41:24 Mail[1366] : Could not connect: (Connected) account: [email blocked] smtp-mail.outlook.com (E63BB455-AE8E-4C8A-96AF-60EA5C7CF433)
hostname: smtp-mail.outlook.com, port: 25, security layer: kCFStreamSocketSecurityLevelNone (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out")

What did you expect instead So email IMAP connection is successful. I can receive emails just fine. Cannot send ANY emails. Error for the SMTP connection with various settings. I did not expect anything to change.

If your problem concerns GPGMail, are other plugins installed in Mail.app? No other plugins installed.

Please attach .png or .jpg screenshots of error messages or steps leading to your problem and remove this line once you're done wrinting your report. Then click the Create button to start a new discussion.

  1. Support Staff 1 Posted by Steve on 05 Nov, 2015 05:00 PM

    Steve's Avatar

    Hey Shai,

    could you temporarily disable GPGMail:

    • shut down mail.app
    • open finder
    • navigate to /Library/Mail/Bundles or ~/Library/Mail/Bundles and copy GPGMail.mailbundle to your desktop
    • now delete GPGMail.mailbundle from the original folder

    Restart mail and check in Mail.app > Preferences if you still see GPGMail. It should be gone.

    To re-enable mail, close Mail.app and move the bundle file back to the Bundles folder.

    With GPGMail disable, does that change anything in regards to your SMTP server issue?

    All the best,
    steve

  2. 2 Posted by shai.levit on 05 Nov, 2015 05:44 PM

    shai.levit's Avatar

    Hi Steve,

    So this is truly odd. I did delete the GPGMail.mailbundle from the Bundle folder in Library/Mail/Bundle. I check to make sure that there is no GPG in the Mail preferences (see image). I rebooted the Mac, re-launched mail and checked the connection doctor. Again, the IMAP connect just fine, but the SMTP fail. Even though there is no more option or encryption tag available, I cannot seem to send mail, only receive.
    Thought - Is there something interfering with the KeyChain software - either the one in GPG or the one in Utilities from Apple ?
    Any other suggestions are greatly appreciated. Please note that I can send mail from my other Windows system - so I know it is not the router or some type of filtering mechanism. I even checked both port options for sending mail 587 and 25. But no avail.

    Thanks for continuing to help me out.

    Shai

  3. Support Staff 3 Posted by Steve on 05 Nov, 2015 06:13 PM

    Steve's Avatar

    Hey Shai,

    neither GPGMail not GPG Keychain is at fault here. You need to to open Mail.app > accounts and double check your settings for the SMTP server for the mail account in question.

    Maybe setting up a new SMTP server with the details given by Microsoft at http://windows.microsoft.com/en-us/windows/outlook/send-receive-fro...#

    there look for "Apps that support IMAP and SMTP" but other than that you'd need to get in touch with Microsoft and ask for help setting up your mail account.

  4. 4 Posted by Shai Levit on 01 Dec, 2015 04:05 PM

    Shai Levit's Avatar

    Hi Steve and staff,

    After some rounds with Apple support and the odd faults of the SMTP sever issue, I was finally back up and in working condition, which includes the GPG Mail plug-in. Works perfectly and as expected. And it was not the tools fault, but some bad voodoo in my routing and router/firewall configuration.

    Thanks for the help, responses and assistance in helping users like myself.

  5. Support Staff 5 Posted by Steve on 02 Dec, 2015 04:31 PM

    Steve's Avatar

    Perfect. Glad, this is solved for you. I'm closing this discussion. If you need further assistance or have questions you can re-open this discussion here or open a new one any time.

    Best, steve

  6. Steve closed this discussion on 02 Dec, 2015 04:31 PM.

  7. Steve re-opened this discussion on 09 Jan, 2016 01:51 PM

  8. Support Staff 6 Posted by Steve on 09 Jan, 2016 01:51 PM

    Steve's Avatar

    Another user (with no GPG Suite or other plug-ins) ran into this bug and reported more details here:

    https://gpgtools.tenderapp.com/discussions/feedback/1770-osx-el-cap...

  9. Steve closed this discussion on 09 Jan, 2016 01:51 PM.

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