[Users] Live.com problem

[Ed Ahlsen-Girard]

My outlook.com address has failed to retrieve since 11/10:

Error
Can't connect to IMAP server: imap-mail.outlook.com:993

Settings unchanged for years.

[Michael Rasmussen]

Which version of Claws? Works here.
⁣Sendt af BlueMail ​

Post by Ed Ahlsen-Girard
Error
Can't connect to IMAP server: imap-mail.outlook.com:993
Settings unchanged for years.
--
Edward Ahlsen-Girard
Ft Walton Beach, FL
_______________________________________________
Users mailing list
https://lists.claws-mail.org/cgi-bin/mailman/listinfo/users

[Ed Ahlsen-Girard]

version 3.17.1 on OpenBSD snapshot of 13 November 2018.

Post by Michael Rasmussen
Which version of Claws? Works here.
⁣Sendt af BlueMail ​
Den 14. nov. 2018 14.00, fra 14.00, Ed Ahlsen-Girard <eagirard at

Post by Ed Ahlsen-Girard
Error
Can't connect to IMAP server: imap-mail.outlook.com:993
Settings unchanged for years.
--
Edward Ahlsen-Girard
Ft Walton Beach, FL
_______________________________________________
Users mailing list
Users at lists.claws-mail.org
https://lists.claws-mail.org/cgi-bin/mailman/listinfo/users

[Michael Rasmussen]

On Wed, 14 Nov 2018 22:12:38 -0600

Post by Ed Ahlsen-Girard
version 3.17.1 on OpenBSD snapshot of 13 November 2018.

Then you would have to provide more info like running claws with option
--debug and send output to the list.
--
Hilsen/Regards
Michael Rasmussen

Get my public GnuPG keys:
michael <at> rasmussen <dot> cc
http://pgp.mit.edu:11371/pks/lookup?op=get&search=0xD3C9A00E
mir <at> datanom <dot> net
http://pgp.mit.edu:11371/pks/lookup?op=get&search=0xE501F51C
mir <at> miras <dot> org
http://pgp.mit.edu:11371/pks/lookup?op=get&search=0xE3E80917
--------------------------------------------------------------
/usr/games/fortune -es says:
The bigger the theory the better.

[Richard]

Date: Thursday, November 15, 2018 07:37:38 +0100
On Wed, 14 Nov 2018 22:12:38 -0600

Post by Ed Ahlsen-Girard
version 3.17.1 on OpenBSD snapshot of 13 November 2018.

Then you would have to provide more info like running claws with
option --debug and send output to the list.

Or ... simply try telnetting to:

imap-mail.outlook.com 993

as a first step and see what happens. The error message you are
showing is vague and your issue could be dns/firewall/routing, in
which case you'll get a hang or error message of some type in
response to the telnet. If it's not a network-related problem you
should get something like:

Trying <ipnumber>...
Connected to imap-mail.outlook.com.
Escape character is '^]'.

in which case the --debug output is the next step.

[Ed Ahlsen-Girard]

Post by Richard

Date: Thursday, November 15, 2018 07:37:38 +0100
From: Michael Rasmussen <mir at miras.org>
On Wed, 14 Nov 2018 22:12:38 -0600

Post by Ed Ahlsen-Girard
version 3.17.1 on OpenBSD snapshot of 13 November 2018.

Then you would have to provide more info like running claws with
option --debug and send output to the list.

imap-mail.outlook.com 993
as a first step and see what happens. The error message you are
showing is vague and your issue could be dns/firewall/routing, in
which case you'll get a hang or error message of some type in
response to the telnet. If it's not a network-related problem you
Trying <ipnumber>...
Connected to imap-mail.outlook.com.
Escape character is '^]'.
in which case the --debug output is the next step.

Telnet connected fine. Sample debug output below:

map-thread.c:446:found imap 0x1d27f3a72d00
[20:39:51] IMAP> 23 STATUS "[Gmail]/Sent Mail" (MESSAGES UIDNEXT UIDVALIDITY UNS
[20:39:51] IMAP< * STATUS "[Gmail]/Sent Mail" (MESSAGES 50 UIDNEXT 51 UIDVALIDIT
[20:39:51] IMAP< 23 OK Success
imap-thread.c:1062:imap status run - end 0
imap-thread.c:462:generic_cb
imap-thread.c:446:found imap 0x1d27f3a72d00
imap-thread.c:1102:imap status - end
imap.c:4874:exists 50, item->item.total_msgs 50
unseen 0, item->item.unread_msgs 0
uid_next 51, item->uid_next 51
uid_val 628018833, item->item.mtime 628018833
imap.c:539:unlocking session 0x1d283d816000
imap.c:4826:getting session...
imap.c:526:locking session 0x1d283d816000 (0)
imap.c:3790:using separator: /
imap-thread.c:1073:imap status - begin
imap-thread.c:446:found imap 0x1d27f3a72d00
imap-thread.c:446:found imap 0x1d27f3a72d00
[20:39:51] IMAP> 24 STATUS "[Gmail]/Spam" (MESSAGES UIDNEXT UIDVALIDITY UNSEEN)
[20:39:51] IMAP< * STATUS "[Gmail]/Spam" (MESSAGES 10 UIDNEXT 789 UIDVALIDITY 62
[20:39:51] IMAP< 24 OK Success
imap-thread.c:1062:imap status run - end 0
imap-thread.c:462:generic_cb
imap-thread.c:446:found imap 0x1d27f3a72d00
imap-thread.c:1102:imap status - end
imap.c:4874:exists 10, item->item.total_msgs 10
unseen 10, item->item.unread_msgs 10
uid_next 789, item->uid_next 789
uid_val 628018830, item->item.mtime 628018830
imap.c:539:unlocking session 0x1d283d816000
imap.c:4826:getting session...
imap.c:526:locking session 0x1d283d816000 (0)
imap.c:3790:using separator: /
imap-thread.c:1073:imap status - begin
imap-thread.c:446:found imap 0x1d27f3a72d00
imap-thread.c:446:found imap 0x1d27f3a72d00
[20:39:51] IMAP> 25 STATUS "[Gmail]/Starred" (MESSAGES UIDNEXT UIDVALIDITY UNSEE
[20:39:51] IMAP< * STATUS "[Gmail]/Starred" (MESSAGES 23 UIDNEXT 28 UIDVALIDITY
[20:39:51] IMAP< 25 OK Success
imap-thread.c:1062:imap status run - end 0
imap-thread.c:462:generic_cb
imap-thread.c:446:found imap 0x1d27f3a72d00
imap-thread.c:1102:imap status - end
imap.c:4874:exists 23, item->item.total_msgs 23
unseen 0, item->item.unread_msgs 0
uid_next 28, item->uid_next 28
uid_val 628018831, item->item.mtime 628018831

imap.c:526:locking session 0x1d283d816000 (0)
imap.c:3790:using separator: /
imap-thread.c:1073:imap status - begin
imap-thread.c:446:found imap 0x1d27f3a72d00
imap-thread.c:446:found imap 0x1d27f3a72d00
[20:39:51] IMAP> 26 STATUS "[Gmail]/Trash" (MESSAGES UIDNEXT UIDVALIDITY UNSEEN)
[20:39:51] IMAP< * STATUS "[Gmail]/Trash" (MESSAGES 0 UIDNEXT 120 UIDVALIDITY 628018829 UNSEEN 0)
[20:39:51] IMAP< 26 OK Success
imap-thread.c:1062:imap status run - end 0
imap-thread.c:462:generic_cb
imap-thread.c:446:found imap 0x1d27f3a72d00
imap-thread.c:1102:imap status - end
imap.c:4874:exists 0, item->item.total_msgs 0
unseen 0, item->item.unread_msgs 0
uid_next 120, item->uid_next 120
uid_val 628018829, item->item.mtime 628018829
imap.c:539:unlocking session 0x1d283d816000
folderview.c:1233:called inc_unlock (lock count 0)
inc.c:359:INC: checking account 4
folderview.c:1160:called inc_lock (lock count 1)
imap.c:4826:getting session...
** Message: 20:39:51.815: Account 'Live.com': Connecting to IMAP server: imap-mail.outlook.com:993...

imap-thread.c:446:found imap 0x1d2855a3c700
imap-thread.c:672:deleting old imap 0x1d2855a3c700
imap-thread.c:563:threaded delete imap posted
imap-thread.c:446:found imap 0x1d2807e51d00
imap-thread.c:462:generic_cb
imap-thread.c:446:found imap 0x1d2807e51d00
imap-thread.c:701:connect 43 with imap 0x1d2807e51d00

** (claws-mail:24024): WARNING **: 20:39:51.968: [20:39:51] SSL/TLS handshake failed

alertpanel.c:253:Creating alert panel dialog...
alertpanel.c:211:called inc_lock (lock count 2)
imap.c:526:locking session 0x1d283d816000 (0)
imap-thread.c:1149:imap noop - begin
imap-thread.c:446:found imap 0x1d27f3a72d00
imap-thread.c:446:found imap 0x1d27f3a72d00
[20:40:41] IMAP> 27 NOOP
imap-thread.c:1135:imap noop run - end 4
imap-thread.c:462:generic_cb
imap-thread.c:446:found imap 0x1d27f3a72d00
imap-thread.c:1176:imap noop - end [EXISTS 0 RECENT 0 EXPUNGE 0 UNSEEN 0 UIDNEXT 0 UIDVAL 0]

** (claws-mail:24024): WARNING **: 20:40:41.081: [20:40:41] IMAP error on imap.gmail.com: stream error


** (claws-mail:24024): WARNING **: 20:40:41.081: [20:40:41] IMAP connection broken

imap.c:4153:noop err 4
imap.c:539:unlocking session 0x1d283d816000

[Michael Rasmussen]

On Thu, 15 Nov 2018 20:48:50 -0600

Post by Ed Ahlsen-Girard
** (claws-mail:24024): WARNING **: 20:39:51.968: [20:39:51] SSL/TLS handshake failed

Above is your error. If you were able to get any meaningful back using
telnet which is plain text then it could indicate that the server does
not speak SSL over port 993 as one could expect.

Instead of telnet try openssl s_client to verify that SSL is infact
working.
--
Hilsen/Regards
Michael Rasmussen

Get my public GnuPG keys:
michael <at> rasmussen <dot> cc
http://pgp.mit.edu:11371/pks/lookup?op=get&search=0xD3C9A00E
mir <at> datanom <dot> net
http://pgp.mit.edu:11371/pks/lookup?op=get&search=0xE501F51C
mir <at> miras <dot> org
http://pgp.mit.edu:11371/pks/lookup?op=get&search=0xE3E80917
--------------------------------------------------------------
/usr/games/fortune -es says:
Let no guilty man escape.
-- U. S. Grant

[Ed Ahlsen-Girard]

Post by Michael Rasmussen
On Thu, 15 Nov 2018 20:48:50 -0600

Post by Ed Ahlsen-Girard
** (claws-mail:24024): WARNING **: 20:39:51.968: [20:39:51] SSL/TLS
handshake failed

Above is your error. If you were able to get any meaningful back using
telnet which is plain text then it could indicate that the server does
not speak SSL over port 993 as one could expect.
Instead of telnet try openssl s_client to verify that SSL is infact
working.
--
Hilsen/Regards
Michael Rasmussen
michael <at> rasmussen <dot> cc
http://pgp.mit.edu:11371/pks/lookup?op=get&search=0xD3C9A00E
mir <at> datanom <dot> net
http://pgp.mit.edu:11371/pks/lookup?op=get&search=0xE501F51C
mir <at> miras <dot> org
http://pgp.mit.edu:11371/pks/lookup?op=get&search=0xE3E80917
--------------------------------------------------------------
Let no guilty man escape.
-- U. S. Grant

Results of openssl s_client below signature. Appears to connect.
--
Edward Ahlsen-Girard
Ft Walton Beach, FL

openssl s_client -connect imap-mail.outlook.com:993
CONNECTED(00000003)
depth=2 C = US, O = DigiCert Inc, OU = www.digicert.com, CN = DigiCert
Global Root CA verify return:1
depth=1 C = US, O = DigiCert Inc, CN = DigiCert Cloud Services CA-1
verify return:1
depth=0 C = US, ST = Washington, L = Redmond, O = Microsoft
Corporation, CN = outlook.com verify return:1
20401814089808:error:04FFF08F:rsa routines:CRYPTO_internal:invalid
digest length:/usr/src/lib/libcrypto/rsa/rsa_sign.c:205:
20401814089808:error:1400907B:SSL routines:CONNECT_CR_KEY_EXCH:bad
signature:/usr/src/lib/libssl/ssl_clnt.c:1572: --- Certificate chain
0 s:/C=US/ST=Washington/L=Redmond/O=Microsoft
Corporation/CN=outlook.com i:/C=US/O=DigiCert Inc/CN=DigiCert Cloud
Services CA-1 1 s:/C=US/O=DigiCert Inc/CN=DigiCert Cloud Services CA-1
i:/C=US/O=DigiCert Inc/OU=www.digicert.com/CN=DigiCert Global Root CA
---
Server certificate
-----BEGIN CERTIFICATE-----
MIIIljCCB36gAwIBAgIQAwuxqX4xVa7w1UuyqyFJJDANBgkqhkiG9w0BAQsFADBL
MQswCQYDVQQGEwJVUzEVMBMGA1UEChMMRGlnaUNlcnQgSW5jMSUwIwYDVQQDExxE
aWdpQ2VydCBDbG91ZCBTZXJ2aWNlcyBDQS0xMB4XDTE4MDgwMTAwMDAwMFoXDTIw
MDgwMTEyMDAwMFowajELMAkGA1UEBhMCVVMxEzARBgNVBAgTCldhc2hpbmd0b24x
EDAOBgNVBAcTB1JlZG1vbmQxHjAcBgNVBAoTFU1pY3Jvc29mdCBDb3Jwb3JhdGlv
bjEUMBIGA1UEAxMLb3V0bG9vay5jb20wggEiMA0GCSqGSIb3DQEBAQUAA4IBDwAw
ggEKAoIBAQDVVNVGkEsBuKY/r/jSWBho6PbsBlIQQSbfncOwmJ/U7GkQtuRQmett
Pg1kysUTQHv03ik6AqSdc0S0ioNPbFDVdmjhU1ctHTapntg2U3xfXk1LG5jfS68n
J5r6yULKwrJqFt1FH9FQlPvo5AXxms27RZSKgj38M3bTd9ckCJYvY3/23Bs7PlBd
bRnz/TByQBTFMMXPVUcEvcQshqhSVF4+/bLQWnDlB2YNGAvYym2CdnQB46g436Ng
viz9Bj52yJnc2OllLN99Pc90ht6exUVg6PBPCr3I3seo9Jpt9xSPg4bNoT1BgZlo
IDscJxjVoFow76n7VazJj8plYpkp4uElAgMBAAGjggVVMIIFUTAfBgNVHSMEGDAW
gBTdUdCiMXOpc66PtAF+XYxXy5/w9zAdBgNVHQ4EFgQUe1dDrggQQeAPjM2DrGt5
5KCmE4owggH0BgNVHREEggHrMIIB54IWKi5jbG8uZm9vdHByaW50ZG5zLmNvbYIW
Ki5ucmIuZm9vdHByaW50ZG5zLmNvbYINKi5ob3RtYWlsLmNvbYIWKi5pbnRlcm5h
bC5vdXRsb29rLmNvbYIKKi5saXZlLmNvbYIMKi5vZmZpY2UuY29tgg8qLm9mZmlj
ZTM2NS5jb22CDSoub3V0bG9vay5jb22CFyoub3V0bG9vay5vZmZpY2UzNjUuY29t
ghthdHRhY2htZW50Lm91dGxvb2subGl2ZS5uZXSCHWF0dGFjaG1lbnQub3V0bG9v
ay5vZmZpY2UubmV0giBhdHRhY2htZW50Lm91dGxvb2sub2ZmaWNlcHBlLm5ldIId
Y2NzLmxvZ2luLm1pY3Jvc29mdG9ubGluZS5jb22CIWNjcy1zZGYubG9naW4ubWlj
cm9zb2Z0b25saW5lLmNvbYILaG90bWFpbC5jb22CFm1haWwuc2VydmljZXMubGl2
ZS5jb22CDW9mZmljZTM2NS5jb22CC291dGxvb2suY29tghJvdXRsb29rLm9mZmlj
ZS5jb22CFHN1YnN0cmF0ZS5vZmZpY2UuY29tghhzdWJzdHJhdGUtc2RmLm9mZmlj
ZS5jb22CFmF0dGFjaG1lbnRzLm9mZmljZS5uZXQwDgYDVR0PAQH/BAQDAgWgMB0G
A1UdJQQWMBQGCCsGAQUFBwMBBggrBgEFBQcDAjCBjQYDVR0fBIGFMIGCMD+gPaA7
hjlodHRwOi8vY3JsMy5kaWdpY2VydC5jb20vRGlnaUNlcnRDbG91ZFNlcnZpY2Vz
Q0EtMS1nMS5jcmwwP6A9oDuGOWh0dHA6Ly9jcmw0LmRpZ2ljZXJ0LmNvbS9EaWdp
Q2VydENsb3VkU2VydmljZXNDQS0xLWcxLmNybDBMBgNVHSAERTBDMDcGCWCGSAGG
/WwBATAqMCgGCCsGAQUFBwIBFhxodHRwczovL3d3dy5kaWdpY2VydC5jb20vQ1BT
MAgGBmeBDAECAjB8BggrBgEFBQcBAQRwMG4wJQYIKwYBBQUHMAGGGWh0dHA6Ly9v
Y3NweC5kaWdpY2VydC5jb20wRQYIKwYBBQUHMAKGOWh0dHA6Ly9jYWNlcnRzLmRp
Z2ljZXJ0LmNvbS9EaWdpQ2VydENsb3VkU2VydmljZXNDQS0xLmNydDAMBgNVHRMB
Af8EAjAAMIIBfAYKKwYBBAHWeQIEAgSCAWwEggFoAWYAdgDuS723dc5guuFCaR+r
4Z5mow9+X7By2IMAxHuJeqj9ywAAAWT01CimAAAEAwBHMEUCIGzave4h94qJi4oH
C3M3mzCavHzpdv1yozBuDSi5/UQFAiEAvvOL8HTp7osSrbr5uXJKElVOiSrzUIeD
kWETqGdprZwAdQCHdb/nWXz4jEOZX73zbv9WjUdWNv9KtWDBtOr/XqCDDwAAAWT0
1CkvAAAEAwBGMEQCIBv3K0OGpvt3aFDVSNOKWgOdN5PRyYhQz000Wf4DTCowAiBG
V/4B6D6sPMyhUmV9MWhnhpeXTuAFPW24OjwKQbyhQQB1ALvZ37wfinG1k5Qjl6qS
e0c4V5UKq1LoGpCWZDaOHtGFAAABZPTUKIQAAAQDAEYwRAIgNlw4dtqF1gJGVowy
MPlv62RUTFb91Yx+TL3buKhL+zkCICynpLMJLoGDlAZPIIixR8QTMW7a3IAdYP5k
5V8wsg3nMA0GCSqGSIb3DQEBCwUAA4IBAQAFcCP8qyQIwiZhOpmDS/kv1Hs0DJCg
t1N8BiBI6ndtq6XvP2GvErtKgrtIrCHi9xuwkrN4FnMUDGbtp0R0sbci6Q0O/viQ
eo4IVuKI/PqyzELvHdr8/MjWXeM1xSGNe4jzJaVAkxU6op9SzRtbAwJ46chSnbxO
QsTMZN/Pb5Hx4EQdgAeyWpsys0mxGAzrrJwMBl6tZgQfSWGpd72fR0yxQIdF5N+7
yyOMnqQRMqnTK9uXfPiYdeeonuMf6POUOOZ4l2e3OkrZ+aZEkikBpGYR+P0wiqK4
ZKfpAx5JRCjfqZbxFSMo250QPiW2ag5pf5d1nJr0TFYqBUM2jkJC4LRe
-----END CERTIFICATE-----
subject=/C=US/ST=Washington/L=Redmond/O=Microsoft \
Corporation/CN=outlook.com
issuer=/C=US/O=DigiCert Inc/CN=DigiCert Cloud Services CA-1
---
No client certificate CA names sent
Server Temp Key: ECDH, P-256, 256 bits
---
SSL handshake has read 3812 bytes and written 7 bytes
---
New, (NONE), Cipher is (NONE)
Server public key is 2048 bit
Secure Renegotiation IS supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
SSL-Session:
Protocol : TLSv1.2
Cipher : 0000
Session-ID:
7225000075F41B7FC00248144B76D4BA56EBF11B0FDD0C0D506A8854CCAFCE85
Session-ID-ctx:
Master-Key:
Start Time: 1542367461
Timeout : 7200 (sec)
Verify return code: 0 (ok)
---

[Paul]

On Fri, 16 Nov 2018 05:31:47 -0600

Post by Ed Ahlsen-Girard
Results of openssl s_client below signature. Appears to connect.

gnutls-cli also produces no error. (claws-mail uses gnutls, openssl),
which suggests a configuration error in your account settings.

What settings are you using?

with regards

Paul

[Jerry]

Post by Michael Rasmussen
On Thu, 15 Nov 2018 20:48:50 -0600

Post by Ed Ahlsen-Girard
** (claws-mail:24024): WARNING **: 20:39:51.968: [20:39:51] SSL/TLS
handshake failed

Above is your error. If you were able to get any meaningful back using
telnet which is plain text then it could indicate that the server does
not speak SSL over port 993 as one could expect.
Instead of telnet try openssl s_client to verify that SSL is infact
working.

Check your settings against the ones recommended by outlook:

https://support.office.com/en-us/article/POP-and-IMAP-email-settings-for-Outlook-8361e398-8af4-4e97-b147-6c6c4ac95353

[Jerry]

Post by Ed Ahlsen-Girard

Post by Michael Rasmussen
On Thu, 15 Nov 2018 20:48:50 -0600

Post by Ed Ahlsen-Girard
** (claws-mail:24024): WARNING **: 20:39:51.968: [20:39:51] SSL/TLS
handshake failed

Above is your error. If you were able to get any meaningful back using
telnet which is plain text then it could indicate that the server does
not speak SSL over port 993 as one could expect.
Instead of telnet try openssl s_client to verify that SSL is infact
working.

Results of openssl s_client below signature. Appears to connect.

//truncated//

I got a slightly different output, but I did request more info.

openssl s_client -connect imap-mail.outlook.com:993 -tls1_2 -showcerts

CONNECTED(00000003)
---
Certificate chain
0 s:/C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/CN=outlook.com
i:/C=US/O=DigiCert Inc/CN=DigiCert Cloud Services CA-1
-----BEGIN CERTIFICATE-----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viz9Bj52yJnc2OllLN99Pc90ht6exUVg6PBPCr3I3seo9Jpt9xSPg4bNoT1BgZlo
IDscJxjVoFow76n7VazJj8plYpkp4uElAgMBAAGjggVVMIIFUTAfBgNVHSMEGDAW
gBTdUdCiMXOpc66PtAF+XYxXy5/w9zAdBgNVHQ4EFgQUe1dDrggQQeAPjM2DrGt5
5KCmE4owggH0BgNVHREEggHrMIIB54IWKi5jbG8uZm9vdHByaW50ZG5zLmNvbYIW
Ki5ucmIuZm9vdHByaW50ZG5zLmNvbYINKi5ob3RtYWlsLmNvbYIWKi5pbnRlcm5h
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-----END CERTIFICATE-----
1 s:/C=US/O=DigiCert Inc/CN=DigiCert Cloud Services CA-1
i:/C=US/O=DigiCert Inc/OU=www.digicert.com/CN=DigiCert Global Root CA
-----BEGIN CERTIFICATE-----
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-----END CERTIFICATE-----
---
Server certificate
subject=/C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/CN=outlook.com
issuer=/C=US/O=DigiCert Inc/CN=DigiCert Cloud Services CA-1
---
No client certificate CA names sent
Peer signing digest: SHA1
Server Temp Key: ECDH, P-256, 256 bits
---
SSL handshake has read 3863 bytes and written 433 bytes
---
New, TLSv1/SSLv3, Cipher is ECDHE-RSA-AES256-GCM-SHA384
Server public key is 2048 bit
Secure Renegotiation IS supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
SSL-Session:
Protocol : TLSv1.2
Cipher : ECDHE-RSA-AES256-GCM-SHA384
Session-ID: 78450000358A06D84EE8AAAAC631BBF14D44672E152C9709D43086E984847EC9
Session-ID-ctx:
Master-Key: D4EE066B6F9087FFFB6CFD2D36EEC9AA165C95CD3E86268E9A9D032B95B5D46F67B7DA22C0218321C45E9399EFE823A3
Key-Arg : None
PSK identity: None
PSK identity hint: None
SRP username: None
Start Time: 1542378556
Timeout : 7200 (sec)
Verify return code: 0 (ok)
---
* OK The Microsoft Exchange IMAP4 service is ready. [QgBOADcAUABSADEAMABDAEEAMAAwADEAOAAuAG4AYQBtAHAAcgBkADEAMAAuAHAAcgBvAGQALgBvAHUAdABsAG8AbwBrAC4AYwBvAG0A]

[Ed Ahlsen-Girard]

Jerry jerry at seibercom.net
Fri Nov 16 15:34:27 CET 2018
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Post by Ed Ahlsen-Girard

Post by Michael Rasmussen
On Thu, 15 Nov 2018 20:48:50 -0600

Post by Ed Ahlsen-Girard
** (claws-mail:24024): WARNING **: 20:39:51.968: [20:39:51]
SSL/TLS handshake failed

Above is your error. If you were able to get any meaningful back
using telnet which is plain text then it could indicate that the
server does not speak SSL over port 993 as one could expect.
Instead of telnet try openssl s_client to verify that SSL is infact
working.

Results of openssl s_client below signature. Appears to connect.

//truncated//
I got a slightly different output, but I did request more info.
openssl s_client -connect imap-mail.outlook.com:993 -tls1_2 -showcerts
CONNECTED(00000003)
---
Certificate chain
0 s:/C=US/ST=Washington/L=Redmond/O=Microsoft

------------------>% (snip)

The problem may have been with the OpenBSD package last week. I've
updated snapshots and all is well. Thanks to all.