openssh bugs - Jan 2022 - [Bug 3380] New: Option -o ConnectTimeout not work

https://bugzilla.mindrot.org/show_bug.cgi?id=3380

            Bug ID: 3380
           Summary: Option -o ConnectTimeout not work
           Product: Portable OpenSSH
           Version: 7.9p1
          Hardware: Other
                OS: Linux
            Status: NEW
          Severity: enhancement
          Priority: P5
         Component: ssh
          Assignee: unassigned-bugs at mindrot.org
          Reporter: massimiliano.cuoghi at systemceramics.com

Created attachment 3565
  --> https://bugzilla.mindrot.org/attachment.cgi?id=3565&action=edit
log of the three commands

The ConnectTimeout option does not work for me, as you can see from the
reports.

If I give the command without options I connect immediately.

With a timeout of less than 130 seconds, it fails with timeout.

With a longer timeout it goes a few more steps but still fails.

uname -a
Linux DG1600223 4.19.0-16-amd64 #1 SMP Debian 4.19.181-1 (2021-03-19)
x86_64 GNU 

cat /etc/ssh/ssh_config

SendEnv LANG LC_*
HashKnownHosts yes
GSSAPIAuthentication yes

cat /root/.ssh/config

Host *
  StrictHostKeyChecking = no
  UserKnownHostsFile = /dev/null
  ControlPath none

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massimiliano.cuoghi at systemceramics.com changed:

           What    |Removed                     |Added
----------------------------------------------------------------------------
           Hardware|Other                       |amd64

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Darren Tucker <dtucker at dtucker.net> changed:

           What    |Removed                     |Added
----------------------------------------------------------------------------
                 CC|                            |dtucker at dtucker.net

--- Comment #1 from Darren Tucker <dtucker at dtucker.net> ---
I think this is bug#3229 which was fixed in the 8.5 release.

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https://bugzilla.mindrot.org/show_bug.cgi?id=3380

--- Comment #2 from massimiliano.cuoghi at systemceramics.com ---
(In reply to Darren Tucker from comment #1)
> I think this is bug#3229 which was fixed in the 8.5 release.
I think they are two different cases

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--- Comment #3 from Darren Tucker <dtucker at dtucker.net>
---
> OpenSSH_7.9p1 Debian-10+deb10u2, OpenSSL 1.1.1d  10 Sep 2019
Firstly, you are using a vendor modified version of OpenSSH.  Can you
reproduce the problem with the stock source from openssh.com?

I can't tell timings from those traces, but the first two are showing
two different behaviours from the remote server:
> ssh -vvv -o ConnectTimeout=30 -p 443 user at srvsysssh.com
[...]
> debug1: connect to address 94.86.175.299 port 443: Connection timed out
> ssh: connect to host srvsysssh.com port 443: Connection timed out
The server fails to establish a TCP connection within 30s.
> $ ssh -vvv -o ConnectTimeout=150 -p 443 user at srvsysssh.com
> OpenSSH_7.9p1 Debian-10+deb10u2, OpenSSL 1.1.1d  10 Sep 2019
[...]
> debug1: Connection established.
> debug3: timeout: 29987 ms remain after connect
[...]
> debug1: Local version string SSH-2.0-OpenSSH_7.9p1 Debian-10+deb10u2
> ssh_exchange_identification: Connection closed by remote host
Assuming the transcription is correct, the connection takes ~120s to
come up, then the TCP connection is established but the server does not
reply to the SSH banner and instead closes the connection after some
amount of time I cannot determine (but presumably a bit less than 30
seconds later).

The third trace looks ok from what you have shown.

Given you're using port 443, is it possible there's a transparent web
proxy in the path?  or one of those HTTPS/SSH multiplexers?  Where are
the significant delays and how long are they?

FWIW your examples work for me both with the stock OpenSSH and a Debian
I happen to have handy (albeit on port 22, which is what the server is
on):
$ ssh -V
OpenSSH_7.9p1 Debian-10+deb10u2, OpenSSL 1.1.1d  10 Sep 2019

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Damien Miller <djm at mindrot.org> changed:

           What    |Removed                     |Added
----------------------------------------------------------------------------
         Resolution|---                         |WORKSFORME
             Status|NEW                         |RESOLVED
                 CC|                            |djm at mindrot.org

--- Comment #4 from Damien Miller <djm at mindrot.org> ---
closing for lack of followup

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