Just to add -- I have, indeed, tried both port 587 and port 465 -- same results.

Point about this being SMTP and not IMAP is noted. Thanks!

Andy

---
Andrew D. Arenson (he/him)                              H 317.964.0493
arenson (at) spatzel.net                                C 317.679.4669


On 2024-06-20 1:18 am, Andrew D Arenson wrote:
I appreciate the advice!

I don't know how to interpret the debug results or the openssl results.

The debug file ends with:

.
.
.
[2024-06-20 01:00:14] External authentication name: aren...@spatzel.net
[2024-06-20 01:00:14] Authenticating (LOGIN)...
[2024-06-20 01:00:14] 5> AUTH LOGIN
[2024-06-20 01:00:14] 5< 334 VXNlcm5hbWU6
[2024-06-20 01:00:14] mutt_sasl_cb_authname: getting authname for
smtp.dreamhost.com:465
[2024-06-20 01:00:14] 5> YXJlbnNvbkBzcGF0emVsLm5ldA==
[2024-06-20 01:00:14] 5< 334 UGFzc3dvcmQ6
[2024-06-20 01:00:14] mutt_sasl_cb_pass: getting password for
aren...@spatzel.net@smtp.dreamhost.com:465
[2024-06-20 01:00:14] 5> aWYgaSBhbSBub3Q=
[2024-06-20 01:00:14] 5< 235 2.7.0 Authentication successful
[2024-06-20 01:00:14] SASL protection strength: 0
[2024-06-20 01:00:14] SASL protection buffer size: 65536
[2024-06-20 01:00:14] 5> MAIL FROM:<aren...@spatzel.net>
[2024-06-20 01:00:15] 5< 250 2.1.0 Ok
[2024-06-20 01:00:15] 5> RCPT TO:<aren...@spatzel.net>
[2024-06-20 01:00:15] 5< 250 2.1.5 Ok
[2024-06-20 01:00:15] updating progress: 0K
[2024-06-20 01:00:15] Sending message... 0K/0.4K (0%)
[2024-06-20 01:00:15] 5> DATA
[2024-06-20 01:00:15] 5< 354 End data with <CR><LF>.<CR><LF>
[2024-06-20 01:00:15] 5> Date: Thu, 20 Jun 2024 01:00:13 -0400
[2024-06-20 01:00:15] 5> From: "Andrew D. Arenson" <aren...@spatzel.net>
[2024-06-20 01:00:15] 5> To: aren...@spatzel.net
[2024-06-20 01:00:15] 5> Subject: testF debug 9
[2024-06-20 01:00:15] 5> Message-ID:
<20240620050013.ga344...@iad1-shared-d12-03.dreamhost.com>
[2024-06-20 01:00:15] 5> MIME-Version: 1.0
[2024-06-20 01:00:15] 5> Content-Type: text/plain; charset=us-ascii
[2024-06-20 01:00:15] 5> Content-Disposition: inline
[2024-06-20 01:00:15] 5>
[2024-06-20 01:00:15] 5> testF
[2024-06-20 01:00:15] 5> --
[2024-06-20 01:00:15] 5> Andrew D. Arenson (he/him)
          H 317.964.0493
[2024-06-20 01:00:15] 5> arenson (at) spatzel.net
          C 317.679.4669
[2024-06-20 01:00:15] 5> .


This looks to me like when I attempt to send an email the
authentication works, the email is transferred from my client to the
SMTP host and then ... nothing. Mutt is hanging instead of receiving
back any sort of confirmation that the email has been accepted/sent,
yeah?

After I've let the connection time out, the following get added to the
debug log:

[2024-06-20 01:02:25] tls_socket_read (The TLS connection was
non-properly terminated.)
[2024-06-20 01:02:29] mutt_socket_close: Attempt to close closed connection.
[2024-06-20 01:02:29] SMTP session failed: read error
[2024-06-20 01:02:39] 4> a0009 NOOP
[2024-06-20 01:02:39] tls_socket_read (The TLS connection was
non-properly terminated.)
[2024-06-20 01:02:43] imap_cmd_step: Error reading server response.
[2024-06-20 01:02:43] imap_exec: command failed:
[2024-06-20 01:08:01] mutt_free_body: unlinking
mutttmp/mutt-iad1-shared-d12-03-22685780-344229-8467167742022354817.
[2024-06-20 01:08:01] Mail not sent.
[2024-06-20 01:08:01] mutt_socket_close: Attempt to close closed connection. [2024-06-20 01:08:01] Mailbox aren...@spatzel.net@imap.dreamhost.com closed
[2024-06-20 01:08:03] mutt_index_menu[792]: Got op 164
[2024-06-20 01:08:03] Mailbox is unchanged.
[2024-06-20 01:08:03] mutt_buffer_pool_free: 10 of 10 returned to pool


When I run openssl I get:

-----------------------------------------------------------------------------------------------------------------------------------
CONNECTED(00000003)
depth=2 C = US, ST = New Jersey, L = Jersey City, O = The USERTRUST
Network, CN = USERTrust RSA Certification Authority
verify return:1
depth=1 C = US, ST = New Jersey, L = Jersey City, O = The USERTRUST
Network, CN = USERTrust RSA Domain Validation Secure Server CA
verify return:1
depth=0 CN = *.dreamhost.com
verify return:1
---
Certificate chain
 0 s:CN = *.dreamhost.com
   i:C = US, ST = New Jersey, L = Jersey City, O = The USERTRUST
Network, CN = USERTrust RSA Domain Validation Secure Server CA
 1 s:C = US, ST = New Jersey, L = Jersey City, O = The USERTRUST
Network, CN = USERTrust RSA Domain Validation Secure Server CA
   i:C = US, ST = New Jersey, L = Jersey City, O = The USERTRUST
Network, CN = USERTrust RSA Certification Authority
 2 s:C = US, ST = New Jersey, L = Jersey City, O = The USERTRUST
Network, CN = USERTrust RSA Certification Authority
   i:C = GB, ST = Greater Manchester, L = Salford, O = Comodo CA
Limited, CN = AAA Certificate Services
 3 s:C = GB, ST = Greater Manchester, L = Salford, O = Comodo CA
Limited, CN = AAA Certificate Services
   i:C = GB, ST = Greater Manchester, L = Salford, O = Comodo CA
Limited, CN = AAA Certificate Services
---
Server certificate
-----BEGIN CERTIFICATE-----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-----END CERTIFICATE-----
subject=CN = *.dreamhost.com

issuer=C = US, ST = New Jersey, L = Jersey City, O = The USERTRUST
Network, CN = USERTrust RSA Domain Validation Secure Server CA

---
No client certificate CA names sent
Peer signing digest: SHA256
Peer signature type: RSA-PSS
Server Temp Key: X25519, 253 bits
---
SSL handshake has read 6324 bytes and written 390 bytes
Verification: OK
---
New, TLSv1.3, Cipher is TLS_AES_256_GCM_SHA384
Server public key is 2048 bit
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
Early data was not sent
Verify return code: 0 (ok)
---
---
Post-Handshake New Session Ticket arrived:
SSL-Session:
    Protocol  : TLSv1.3
    Cipher    : TLS_AES_256_GCM_SHA384
Session-ID: AB63AFB29FC844C89796FADA4DEAB545A1DA8A8C7B2DB7EF95A2C7DA3CBFB180
    Session-ID-ctx:
    Resumption PSK:
E56CFEB8E5BA6A773A960688B3FBBAFBEEF1319997A139BD6C5ECDB7255C3CF3624DF66A959C2B9DD8281D4F7D0D03BB
    PSK identity: None
    PSK identity hint: None
    SRP username: None
    TLS session ticket lifetime hint: 7200 (seconds)
    TLS session ticket:
0000 - 4c 5d d9 a6 05 57 0f 1b-aa ab e5 d3 0f 32 4d 92 L]...W.......2M. 0010 - ec a2 37 12 2c 18 4a 07-4f b6 4d b4 25 c3 bd 92 ..7.,.J.O.M.%... 0020 - ad 87 af d6 68 ae 94 22-33 46 ab eb e1 e2 84 18 ....h.."3F...... 0030 - 73 f7 94 6a 27 84 66 d1-f7 b8 3c d9 df 9c 5f b1 s..j'.f...<..._. 0040 - e6 d5 fc ac e7 10 1e b1-64 6f 4d f8 be 6b 0a 26 ........doM..k.& 0050 - 47 02 36 ea e6 8a 6b 77-97 1a 9b 25 52 7c b2 b3 G.6...kw...%R|.. 0060 - f0 19 4e 8c 43 8f 62 d3-7d 57 40 bd 39 81 0c 4e ..N.C.b.}W@.9..N 0070 - 82 cd f1 cd bf 23 42 ab-34 e6 7a 56 7a 86 98 26 .....#B.4.zVz..& 0080 - cf af 24 a9 7e 5b 82 2b-92 cd 05 62 d9 e8 2e 9c ..$.~[.+...b.... 0090 - e7 55 24 81 84 6f 4f 87-34 21 e1 bd 92 7e a2 35 .U$..oO.4!...~.5 00a0 - fb 8d 39 4e f9 bf d0 a0-8a 2c 9f 33 9e 24 15 04 ..9N.....,.3.$.. 00b0 - 98 95 39 b9 db 08 4c 51-67 05 3f b8 c0 25 bd 1b ..9...LQg.?..%.. 00c0 - 22 29 24 2c 3b 02 44 df-5f 4f b1 df 70 af 4e 46 ")$,;.D._O..p.NF

    Start Time: 1718860139
    Timeout   : 7200 (sec)
    Verify return code: 0 (ok)
    Extended master secret: no
    Max Early Data: 0
---
read R BLOCK
220 pdx1-sub0-mail-a206.dreamhost.com ESMTP
-----------------------------------------------------------------------------------------------------------------------------------


I don't know how to interpret a lot of that, but I don't see any obvious errors.


I have a little experience compiling code, but not enough to jump into
doing so unless I really need to. Still, if there's no other
resolution in a couple of days, I might try it.

Thank you, again!

Andy

---
Andrew D. Arenson (he/him)                              H 317.964.0493
arenson (at) spatzel.net                                C 317.679.4669


On 2024-06-20 12:13 am, Will Yardley wrote:
On Wed, Jun 19, 2024 at 11:43:54PM -0400, Andrew D Arenson wrote:
Today, after working for years, my IMAP connection to Dreamhost has started hanging when I attempt to send an email, showing a message like: "Sending
message... 0K/0.4K (0%)".

This is mutt version 1.13.2. I have asked Dreamhost support, today, if they will update the version of mutt, but I'm not holding my breath. I suppose I could try to compile it myself in my non-root user account. I don't know how
feasible that would be.

I doubt they'll update it past the underlying Debian version. Should
work fine (building and compiling your own) -- I've done it before, and
I would bet the dependencies you need should be available, though you
may need to build newer versions of some other programs locally as well.
Just set the prefix to your home directory;

Let me know if you don't get it sorted out.

Just keep in mind that, since sending mail doesn't use IMAP, I would
guess this is more likely s an SMTP issue vs. an IMAP issue.

You could try using port 587 vs 465 and see if that helps.

Also, you should be able to just use `sendmail` to send mail on one of
the hosting machines, at least assuming it's still using an outgoing
relayhost, though it may be a little more likely to get spam filtered.

I would try running mutt with a higher debug level and see if the debug
files that creates give you any additional information about what's
going on / why it's hanging.

You can also use tools like nc or openssl to check, for example:

$ openssl s_client -starttls smtp -crlf -connect smtp.dreamhost.com:587
 $ openssl s_client -connect smtp.dreamhost.com:465

(these work from me, even locally, so I don't think there's a connection
issue, but it may let you test out some stuff).

w

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