Connection could not be established with host mail.domain.com [Connection timed out #110]

[humptydumpty]

Initial posting to keep my sanity while I investigate further. I'm not sure when it started, but I cannot send mail from my Freescout (probably after updating to CR 8.2). I'm getting error:

Connection could not be established with host mail.domain.com [Connection timed out #110]

FreeScout package 1.11.18

I'm installing CR 8.2.1 to see if that does anything. I'll try reinserting the pass for the mailbox as the "mailbox test" fails to send, but the regular FS app works fine. I didn't change anything on my end.

Edit 1: so freescout failed to send the mailbox test and spat an error: make sure port 587 is open. I'm guessing Hetzner changed something?

Edit 2: Port 587 is open according to a test I ran on https://www.yougetsignal.com/tools/open-ports/

Edit 3: Now I'm getting error: mail.domain.com is not available on 993 port. Make sure that mail.domain.com address is correct and that outgoing port 993 on YOUR server is open. I checked using the online site above, and port 993 is open.

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manage > mail settings > system emails > send test to this test is being sent and received as expected

manage > mailbox > connection settings > sending emails and fetching emails both of these are failing

Edit 4: In my CR dashboard > Profile > App Password: I created a new pass and saved that for my mailbox in FS. Issue persists.

Sending/Receiving at the mailbox in Roundcube works correctly. It's definitely a Freescout issue and not SMTP/hosting/port related.

Edit 5: OK, so under Manage > Logs

Fetch Errors:

Error: connection failed - stream_socket_client(): Unable to connect to ssl://mail.domain.com:993 (Connection timed out); File: /app/code/overrides/webklex/php-imap/src/Connection/Protocols/ImapProtocol.php (94)

Send Errors:

 Connection could not be established with host mail.domain.com [Connection timed out #110]; File: /app/code/overrides/swiftmailer/swiftmailer/lib/classes/Swift/Transport/StreamBuffer.php (271) 

[humptydumpty]

Under Manage > System > Status:

App Version 	1.8.159
Date & Time 	Dec 20, 2024 15:49
Timezone (.env) 	America/Chicago (GMT-0600)
Protocol 	HTTPS
DB 	Mysql (8.0.37-0ubuntu0.22.04.3)
Web Server 	Apache/2.4.58 (Ubuntu)
PHP Version 	PHP 8.3.6
PHP upload_max_filesize / post_max_size 	5G / 5G
PHP Extensions
OpenSSL 	OK
PDO 	OK
Mbstring 	OK
Tokenizer 	OK
JSON 	OK
XML 	OK
IMAP 	OK
GD 	OK
fileinfo 	OK
ZIP 	OK
iconv 	OK
cURL 	OK
DOM 	OK
libxml 	OK
intl 	OK
pcntl (console PHP) 	OK
Functions
shell_exec (PHP) 	OK
proc_open (PHP) 	OK
fpassthru (PHP) 	OK
symlink (PHP) 	OK
iconv (PHP) 	OK
pcntl_signal (console PHP) 	OK
ps (shell) 	OK
Permissions
These folders must be writable by web server user (www-data). Recommended permissions: 775
storage/app/ 	OK
storage/framework/ 	OK
storage/framework/cache/data/ 	OK
storage/logs/ 	OK
bootstrap/cache/ 	OK
public/css/builds/ 	OK
public/js/builds/ 	OK
public/modules/ 	OK
Modules/ 	OK
public/storage (symlink) 	OK
.env 	OK

For reference: https://github.com/freescout-help-desk/freescout/wiki/Fetching-Emails#troubleshooting-fetching

@staff possible fix? unsure how to implement this myself https://github.com/freescout-help-desk/freescout/issues/3823#issuecomment-1965724963

P.S. I'm on v8.2.1 (Ubuntu 24.04 LTS)

[joseph]

To narrow down the problem: a) is mail server running under Services? b) are you able to connect with some other mail client? maybe install some webmail like roundcube and check if it can check mail.

[humptydumpty]

@joseph service is all green and yes roundcube works fine. I can send and receive mail to all my mailboxes including the FreeScout ones in roundcube. It just doesn’t work in fs. This stopped working suddenly on its own.

Here's the result of the test initiated from: Manage > Settings > Mail Settings > Send Test To

Under Manage > Mailboxes > Connection Settings > Sending Emails > Send Test To resulting error says to make sure port 587 is open and it is since I checked using an online tool by entering my server IP and port 587 and it spat out OPEN. The same goes for fetching emails and says check port 993 and that is open too, so it's not a port issue.

Off the top of my head I did the following troubleshooting steps:

• Manage > System > Status: It's all OK and queue:work Running
• Manage > System > Tools > Clear Cache
• Restarted app manually
• App updated overnight to package 1.11.19
• Checked ports 587 and 993 using online website and confirmed they are OPEN
• Checked logs as mentioned in FS Troubleshooting page and posted results in initial post
• Created a new app password (mail) to use with my mailbox (not the issue as my other FS mailboxes aren't working too)
• Can confirm CR mailserver is working fine as I can send/receive mail in Roundcube to all mailboxes including my Freescount mailboxes. I can also check/send mail from iOS mail app.
• Freescout test mail settings sent and received the email just fine so the mail settings (SMTP Mailgun) is working in the app. It just refuses to send/fetch at the mailbox level.

Log errors are:

Error: connection failed - stream_socket_client(): Unable to connect to ssl://mail.domain.com:993 (Connection timed out); File: /app/code/overrides/webklex/php-imap/src/Connection/Protocols/ImapProtocol.php (94)

 Connection could not be established with host mail.domain.com [Connection timed out #110]; File: /app/code/overrides/swiftmailer/swiftmailer/lib/classes/Swift/Transport/StreamBuffer.php (271) 

I just opened a ticket upstream: https://github.com/freescout-help-desk/freescout/issues/4441