Dovecot 2.3.20 including it's submission server works well with all sorts of clients, but Outlook.

Outlook works / can connect to Dovecot IMAP service with same certificate TLS config, but it fails to connect using SMTPs on port 465. Other clients connect and send mails without problem, also openssl s_client can connect and reports no problems.

I tried with Outlook Version 365 on Windows 11 (no cloud) and "Microsoft® Outlook® 2021 MSO (Version 2304 Build 16.0.16327.20200) 64-bit".

I already enabled all submission_client_workarounds and lowered min_ssl_version from TLSv1.2 to TLSv1, but that changed nothing.

I can see nothing failing in the logs, thought the OL connection wizard always check IMAP and SMTP together, so it's hard to say what the problem is.

The same two Outlook version connect without a problem to Postfix authenticating via SASL to Dovecot also requiring a minimum TLS version of 1.2.
They just wont connect with Dovecot submission server.

Any ideas what's wrong, or how to debug that further?

Ralf

--

Ralf Becker
EGroupware GmbH [www.egroupware.org]
Handelsregister HRB Kaiserslautern 3587
Geschäftsführer Birgit und Ralf Becker
Leibnizstr. 17, 67663 Kaiserslautern, Germany
Telefon +49 631 31657-0
# 2.3.20 (80a5ac675d): /etc/dovecot/dovecot.conf
# Pigeonhole version 0.5.20 (149edcf2)
# OS: Linux 4.19.0-23-amd64 x86_64 Ubuntu 20.04.6 LTS 
# Hostname: testbox.egroupware.org
auth_master_user_separator = *
first_valid_uid = 90
log_path = /dev/stderr
mail_attribute_dict = file:%h/dovecot-metadata
mail_gid = dovecot
mail_location = mdbox:~/mdbox
mail_plugins = acl quota mail_lua notify push_notification push_notification_lua
mail_uid = dovecot
mail_vsize_bg_after_count = 100
managesieve_notify_capability = mailto
managesieve_sieve_capability = fileinto reject envelope encoded-character 
vacation subaddress comparator-i;ascii-numeric relational regex imap4flags copy 
include variables body enotify environment mailbox date index ihave duplicate 
mime foreverypart extracttext
namespace inbox {
  inbox = yes
  location = 
  mailbox Archive {
    auto = subscribe
    special_use = \Archive
  }
  mailbox Drafts {
    auto = subscribe
    special_use = \Drafts
  }
  mailbox Junk {
    auto = subscribe
    special_use = \Junk
  }
  mailbox Sent {
    auto = subscribe
    special_use = \Sent
  }
  mailbox "Sent Messages" {
    auto = no
    special_use = \Sent
  }
  mailbox Templates {
    auto = subscribe
  }
  mailbox Trash {
    auto = subscribe
    special_use = \Trash
  }
  prefix = INBOX/
  separator = /
}
namespace users {
  location = mdbox:%%h/mdbox
  prefix = user/%%n/
  separator = /
  type = shared
}
passdb {
  args = /etc/dovecot/dovecot-sql-master.conf.ext
  driver = sql
  master = yes
  result_success = continue
}
passdb {
  args = /etc/dovecot/dovecot-sql.conf.ext
  driver = sql
}
plugin {
  acl = vfile:/etc/dovecot/global-acls:cache_secs=300
  acl_shared_dict = file:/var/dovecot/shared-mailboxes.db
  push_lua_url = http://#hidden_use-P_to_show#@push:9501/
  push_notification_driver = lua:file=/etc/dovecot/dovecot-push.lua
  quota = count:User quota
  quota_rule = *:storage=10GB
  quota_vsizes = yes
  sieve = file:~/sieve;active=~/.dovecot.sieve
}
protocols = " imap lmtp sieve pop3 submission"
service lmtp {
  inet_listener lmtp {
    port = 24
  }
}
service submission-login {
  inet_listener smtps {
    port = 465
    ssl = yes
  }
}
ssl = required
ssl_cert = </etc/dovecot/certificate.pem
ssl_cipher_list = 
ECDHE-ECDSA-AES128-GCM-SHA256:ECDHE-RSA-AES128-GCM-SHA256:ECDHE-ECDSA-AES256-GCM-SHA384:ECDHE-RSA-AES256-GCM-SHA384:ECDHE-ECDSA-CHACHA20-POLY1305:ECDHE-RSA-CHACHA20-POLY1305:DHE-RSA-AES128-GCM-SHA256:DHE-RSA-AES256-GCM-SHA384
ssl_dh = # hidden, use -P to show it
ssl_key = # hidden, use -P to show it
submission_client_workarounds = whitespace-before-path mailbox-for-path 
implicit-auth-external
submission_host = smtp:25
submission_relay_host = smtp
submission_relay_trusted = yes
userdb {
  driver = prefetch
}
userdb {
  args = /etc/dovecot/dovecot-sql.conf.ext
  driver = sql
}
protocol lmtp {
  mail_plugins = acl quota mail_lua notify push_notification 
push_notification_lua sieve
}
protocol imap {
  imap_metadata = yes
  mail_plugins = acl quota mail_lua notify push_notification 
push_notification_lua acl imap_acl quota imap_quota
}
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