I have an aging WinXP Embedded SP3 box (don't judge; We're in the process of deprecating it) which need to send email for status updates etc.
This used to use GMail but they're going to turn off support for insecure apps soon so we need a work around to resolve the issue in the short term. To that end, I've set up a ubuntu-linux-based postfix (v3.4.13) server and have tried to configure it to allow TLS v1.0 connections.
On newer (Windows 10 based machines) running the exact same client, they're able to successfully connect in and send email. For some reason though, the XP machine errors out.
Is there a setting I need to alter in postfix to allow these aged connections?
Failed connection example (postfix logs):
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: initializing the server-side TLS engine
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: connect from unknown[62.232.130.246]
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: setting up TLS connection from unknown[62.232.130.246]
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: unknown[62.232.130.246]: TLS cipher list "aNULL:-aNULL:HIGH:MEDIUM:+RC4:@STRENGTH"
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: SSL_accept:before SSL initialization
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: read from 558F3C6A5600 [558F3C6AC5A3] (5 bytes => -1 (0xFFFFFFFFFFFFFFFF))
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: read from 558F3C6A5600 [558F3C6AC5A3] (5 bytes => 5 (0x5))
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: 0000 16 03 01 00 41 ....A
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: read from 558F3C6A5600 [558F3C6AC5A8] (65 bytes => 65 (0x41))
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: 0000 01 00 00 3d 03 01 62 3c|93 7a a3 47 25 d5 46 cd ...=..b< .z.G%.F.
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: 0010 b6 ca 43 77 7c 91 23 47|60 f7 bb 1a 88 04 81 62 ..Cw|.#G `......b
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: 0020 07 e3 ac 35 20 1f 00 00|16 00 04 00 05 00 0a 00 ...5 ... ........
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: 0030 09 00 64 00 62 00 03 00|06 00 13 00 12 00 63 01 ..d.b... ......c.
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: 0040 - <SPACES/NULLS>
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: SSL_accept:before SSL initialization
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: write to 558F3C6A5600 [558F3C6B4750] (7 bytes => 7 (0x7))
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: 0000 15 03 01 00 02 02 28 ......(
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: SSL3 alert write:fatal:handshake failure
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: SSL_accept:error in error
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: SSL_accept error from unknown[62.232.130.246]: -1
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: warning: TLS library problem: error:1417A0C1:SSL routines:tls_post_process_client_hello:no shared cipher:../ssl/statem/statem_srvr.c:2283:
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: lost connection after STARTTLS from unknown[62.232.130.246]
Mar 24 15:51:22 smtp-relay postfix/smtpd[83942]: disconnect from unknown[62.232.130.246] ehlo=1 starttls=0/1 commands=1/2
Successful connection from a win-10 machine (binary sequences cut short for brevity):
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: initializing the server-side TLS engine
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: connect from unknown[62.232.130.246]
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: setting up TLS connection from unknown[62.232.130.246]
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: unknown[62.232.130.246]: TLS cipher list "aNULL:-aNULL:HIGH:MEDIUM:+RC4:@STRENGTH"
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: SSL_accept:before SSL initialization
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: read from 55CE58FD8490 [55CE590115A3] (5 bytes => -1 (0xFFFFFFFFFFFFFFFF))
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: read from 55CE58FD8490 [55CE590115A3] (5 bytes => 5 (0x5))
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0000 16 03 01 00 7a ....z
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: read from 55CE58FD8490 [55CE590115A8] (122 bytes => 122 (0x7A))
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0000 01 00 00 76 03 01 62 3c|92 0b e0 5b 1a 7f 9e 24 ...v..b< ...[...$
...
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0070 00 00 17 00 00 ff 01 00|01 ........ .
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0079 - <SPACES/NULLS>
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: SSL_accept:before SSL initialization
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: SSL_accept:SSLv3/TLS read client hello
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: SSL_accept:SSLv3/TLS write server hello
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: write to 55CE58FD8490 [55CE59019750] (4096 bytes => 4096 (0x1000))
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0000 16 03 01 00 41 02 00 00|3d 03 01 4d d2 77 f9 9c ....A... =..M.w..
...
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0ff0 e9 ec e3 86 00 de 9d 10|e3 38 fa a4 7d b1 d8 e8 ........ .8..}...
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: SSL_accept:SSLv3/TLS write certificate
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: SSL_accept:SSLv3/TLS write key exchange
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: write to 55CE58FD8490 [55CE59019750] (330 bytes => 330 (0x14A))
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0000 49 82 84 06 9b 2b e8 6b|4f 01 0c 38 77 2e f9 dd I....+.k O..8w...
...
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0130 bb bf c2 b5 eb 25 5e 18|74 6e ca ad 10 ee 91 51 .....%^. tn.....Q
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0140 2f 16 03 01 00 04 0e /......
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0147 - <SPACES/NULLS>
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: SSL_accept:SSLv3/TLS write server done
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: read from 55CE58FD8490 [55CE590115A3] (5 bytes => -1 (0xFFFFFFFFFFFFFFFF))
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: read from 55CE58FD8490 [55CE590115A3] (5 bytes => 5 (0x5))
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0000 16 03 01 00 25 ....%
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: read from 55CE58FD8490 [55CE590115A8] (37 bytes => 37 (0x25))
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0000 10 00 00 21 20 01 8c 9c|11 84 58 2d d6 b3 77 7c ...! ... ..X-..w|
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0010 5c d0 87 bd 98 e7 0e a1|dd 10 51 c8 27 98 e9 3e \....... ..Q.'..>
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0020 cb 64 24 7a 0a .d$z.
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: SSL_accept:SSLv3/TLS write server done
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: read from 55CE58FD8490 [55CE590115A3] (5 bytes => 5 (0x5))
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0000 14 03 01 00 01 .....
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: read from 55CE58FD8490 [55CE590115A8] (1 bytes => 1 (0x1))
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0000 01 .
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: SSL_accept:SSLv3/TLS read client key exchange
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: read from 55CE58FD8490 [55CE590115A3] (5 bytes => 5 (0x5))
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0000 16 03 01 00 30 ....0
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: read from 55CE58FD8490 [55CE590115A8] (48 bytes => 48 (0x30))
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0000 a4 a1 7c 35 01 99 6f 54|16 81 3a 80 00 a4 2e 99 ..|5..oT ..:.....
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0010 b1 2a 95 89 f3 37 0e 96|21 25 06 cc c8 8b 57 4e .*...7.. !%....WN
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0020 16 46 5f 54 0f 77 14 59|47 30 00 9e a5 6a b9 5f .F_T.w.Y G0...j._
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: SSL_accept:SSLv3/TLS read change cipher spec
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: SSL_accept:SSLv3/TLS read finished
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: unknown[62.232.130.246]: Issuing session ticket, key expiration: 1648138531
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: SSL_accept:SSLv3/TLS write session ticket
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: SSL_accept:SSLv3/TLS write change cipher spec
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: write to 55CE58FD8490 [55CE59019750] (250 bytes => 250 (0xFA))
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 0000 16 03 01 00 ba 04 00 00|b6 00 00 1c 20 00 b0 b0 ........ .... ...
...
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: 00f0 db fc 56 30 de fc cf b4|70 68 ..V0.... ph
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: SSL_accept:SSLv3/TLS write finished
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: Anonymous TLS connection established from unknown[62.232.130.246]: TLSv1 with cipher ECDHE-RSA-AES256-SHA (256/256 bits)
Mar 24 15:45:32 smtp-relay postfix/smtpd[83924]: read from 55CE58FD8490 [55CE590115A3] (5 bytes => -1 (0xFFFFFFFFFFFFFFFF))
Mar 24 15:45:33 smtp-relay postfix/smtpd[83924]: read from 55CE58FD8490 [55CE590115A3] (5 bytes => 0 (0x0))
Mar 24 15:45:33 smtp-relay postfix/smtpd[83924]: lost connection after STARTTLS from unknown[62.232.130.246]
Mar 24 15:45:33 smtp-relay postfix/smtpd[83924]: disconnect from unknown[62.232.130.246] ehlo=1 starttls=1 commands=2
