I am trying to use exim as a client with my school's email provider, microsoft, as the server. Setups very similar to what I'm using worked a few months ago.
My immediate question is whether the transcript at the bottom gives any clues about the problem. In particular, does the absence of a user account from the transcript mean it is not attempting to login as me? That would be consistent with the error message 530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM [BYAPR08CA0053.namprd08.prod.outlook.com] Comments/Theories 1. Despite my "user login not attempted" theory above, a subsequent session with -d+lookup shows the account name and password successfully looked up by the authenticator. 2. Campus has introduced two-factor authentication with Duo (after the usual login you have to give a one-time code, usually received on your cell). I had hoped that wouldn't affect the email over SMTP, but it may have. Since my exim server is not wired up to support this, that would cause a failure. Does the fact that there are apparently two separate transmissions of gibberish at authentication time indicate two different "passwords" are being required? I have a feeling the first one may just be an encoded version of my account name (see concern 1). 3. Toward the end: "cannot use sendfile for body: spoolfile not wireformat". I was trying to send a file saved from mutt. Perhaps it's not in the right format? In that case, the "anonymous mail" might reflect, e.g., a missing envelope sender. Against this a) the login authentication failure happened earlier and b) sending mail from mutt direct to my local exim failed in the same way (and that certainly should have been in the right format). 4. The list of authenticators does not include LOGIN. However, it does have PLAINTEXT, which I imagine is what's used (if that list is relevant at all when exim is the client). I'm running on Debian buster. Transcript, with a few edits for convenience and security: # date; exim -bm -d-all+auth+dns+rewrite+transport+timestamp -f [email protected] -t < ~ross/testmail Mon 08 Jul 2019 02:55:41 PM PDT 14:55:41 Exim version 4.92 uid=0 gid=0 pid=1218 D=2a000028 Support for: crypteq iconv() IPv6 GnuTLS move_frozen_messages DANE DKIM DNSSEC Event OCSP PRDR SOCKS TCP_Fast_Open Lookups (built-in): lsearch wildlsearch nwildlsearch iplsearch cdb dbm dbmjz dbmnz dnsdb dsearch nis nis0 passwd Authenticators: cram_md5 plaintext Routers: accept dnslookup ipliteral manualroute queryprogram redirect Transports: appendfile/maildir/mailstore autoreply lmtp pipe smtp Fixed never_users: 0 Configure owner: 0:0 Size of off_t: 8 Compiler: GCC [8.3.0] Library version: Glibc: Compile: 2.28 Runtime: 2.28 Library version: BDB: Compile: Berkeley DB 5.3.28: (September 9, 2013) Runtime: Berkeley DB 5.3.28: (September 9, 2013) Library version: GnuTLS: Compile: 3.6.7 Runtime: 3.6.7 Library version: PCRE: Compile: 8.39 Runtime: 8.39 2016-06-14 WHITELIST_D_MACROS: "OUTGOING" TRUSTED_CONFIG_LIST: "/etc/exim4/trusted_configs" 14:55:41 configuration file is /var/lib/exim4/config.autogenerated 14:55:41 log selectors = 0000cffc c6401022 00000001 14:55:41 cwd=/etc/exim4 6 args: exim -bm -d-all+auth+dns+rewrite+transport+timestamp -f [email protected] -t 14:55:41 trusted user 14:55:41 admin user 14:55:41 rewritten sender = [email protected] 14:55:41 rewrite_one_header: type=F: 14:55:41 From: Ross Boylan <[email protected]> 14:55:41 rewrite_one_header: type=T: 14:55:41 To: [email protected] 14:55:41 LOG: MAIN 14:55:41 <= [email protected] U=root P=local S=582 14:55:41 >>>>>>>>>>>>>>>> Exim pid=1218 (main) terminating with rc=0 >>>>>>>>>>>>>>>> 14:55:41 Exim version 4.92 uid=118 gid=124 pid=1219 D=2a000028 [config info repeated here] 14:55:41 admin user 14:55:41 R: smarthost for [email protected] 14:55:42 >>>>>>>>>>>>>>>> Remote deliveries >>>>>>>>>>>>>>>> 14:55:42 --------> [email protected] <-------- 14:55:42 T: remote_smtp_smarthost for [email protected] 14:55:42 remote_smtp_smarthost transport entered 14:55:42 [email protected] 14:55:42 hostlist: 14:55:42 'SJC-efz.ms-acdc.office.com' IP 52.96.3.178 port 587 14:55:42 'SJC-efz.ms-acdc.office.com' IP 40.97.220.34 port 587 14:55:42 'SJC-efz.ms-acdc.office.com' IP 52.96.36.82 port 587 14:55:42 'SJC-efz.ms-acdc.office.com' IP 52.96.36.114 port 587 14:55:42 checking status of SJC-efz.ms-acdc.office.com 14:55:42 no host retry record 14:55:42 no message retry record 14:55:42 SJC-efz.ms-acdc.office.com [52.96.3.178]:587 retry-status = usable 14:55:42 delivering 1hkbbp-0000Je-JW to SJC-efz.ms-acdc.office.com [52.96.3.178] ([email protected]) 14:55:42 Transport port=25 replaced by host-specific port=587 14:55:42 Connecting to SJC-efz.ms-acdc.office.com [52.96.3.178]:587 ... connected 14:55:43 read response data: size=110 14:55:43 SMTP<< 220 BYAPR04CA0001.outlook.office365.com Microsoft ESMTP MAIL Service ready at Mon, 8 Jul 2019 21:55:42 +0000 14:55:43 SMTP>> EHLO barley.betterworld.us 14:55:43 cmd buf flush 28 bytes 14:55:43 read response data: size=204 14:55:43 SMTP<< 250-BYAPR04CA0001.outlook.office365.com Hello [66.181.128.6] 14:55:43 250-SIZE 157286400 14:55:43 250-PIPELINING 14:55:43 250-DSN 14:55:43 250-ENHANCEDSTATUSCODES 14:55:43 250-STARTTLS 14:55:43 250-8BITMIME 14:55:43 250-BINARYMIME 14:55:43 250-CHUNKING 14:55:43 250 SMTPUTF8 14:55:43 SMTP>> STARTTLS 14:55:43 cmd buf flush 10 bytes 14:55:43 read response data: size=29 14:55:43 SMTP<< 220 2.0.0 SMTP server ready 14:55:44 SMTP>> EHLO barley.betterworld.us 14:55:44 cmd buf flush 28 bytes 14:55:44 read response data: size=214 14:55:44 SMTP<< 250-BYAPR04CA0001.outlook.office365.com Hello [66.181.128.6] 14:55:44 250-SIZE 157286400 14:55:44 250-PIPELINING 14:55:44 250-DSN 14:55:44 250-ENHANCEDSTATUSCODES 14:55:44 250-AUTH LOGIN XOAUTH2 14:55:44 250-8BITMIME 14:55:44 250-BINARYMIME 14:55:44 250-CHUNKING 14:55:44 250 SMTPUTF8 14:55:44 using PIPELINING 14:55:44 CHUNKING usable 14:55:44 using DSN 14:55:44 scanning authentication mechanisms 14:55:44 SMTP>> AUTH LOGIN 14:55:44 cmd buf flush 12 bytes 14:55:44 read response data: size=18 14:55:44 SMTP<< 334 [gibberish] 14:55:44 SMTP>> **************************** 14:55:44 cmd buf flush 30 bytes 14:55:44 read response data: size=18 14:55:44 SMTP<< 334 [different gibberish] 14:55:44 SMTP>> ************************ 14:55:44 cmd buf flush 26 bytes 14:55:50 read response data: size=81 14:55:50 SMTP<< 535 5.7.3 Authentication unsuccessful [BYAPR04CA0001.namprd04.prod.outlook.com] 14:55:50 login authenticator yielded 2 14:55:50 LOG: MAIN 14:55:50 login authenticator failed H=SJC-efz.ms-acdc.office.com [52.96.3.178] 535 5.7.3 Authentication unsuccessful [BYAPR04CA0001.namprd04.prod.outlook.com] 14:55:50 SMTP>> MAIL FROM:<[email protected]> SIZE=1623 14:55:50 SMTP>> RCPT TO:<[email protected]> 14:55:50 will write message using CHUNKING 14:55:50 rewrite_one_header: type=F: 14:55:50 From: Ross Boylan <[email protected]> 14:55:50 LOG: address_rewrite MAIN 14:55:50 "[email protected]" from from: rewritten as "[email protected]" by rule 1 14:55:50 newlen=41 newtype=F newtext: 14:55:50 From: Ross Boylan <[email protected]> 14:55:50 remainder: 14:55:50 rewrite_one_header: type=T: 14:55:50 To: [email protected] 14:55:50 LOG: address_rewrite MAIN 14:55:50 "[email protected]" from to: rewritten as "[email protected]" by rule 1 14:55:50 newlen=25 newtype=T newtext: 14:55:50 To: [email protected] 14:55:50 remainder: 14:55:50 SMTP>> BDAT 585 LAST 14:55:50 cmd buf flush 100 bytes (more expected) 14:55:50 cannot use sendfile for body: spoolfile not wireformat 14:55:50 writing data block fd=6 size=585 timeout=300 14:55:50 sync_responses expect mail 14:55:55 read response data: size=129 14:55:55 SMTP<< 530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM [BYAPR04CA0001.namprd04.prod.outlook.com] 14:55:55 bad response for MAIL 14:55:55 LOG: MAIN 14:55:55 H=SJC-efz.ms-acdc.office.com [52.96.3.178] TLS error on connection (recv): The TLS connection was non-properly terminated. 14:55:55 SMTP(No such file or directory)<< 14:55:55 ok=0 send_quit=1 send_rset=1 continue_more=0 yield=0 first_address is NULL 14:55:55 SMTP>> QUIT 14:55:55 cmd buf flush 6 bytes 14:55:55 LOG: MAIN 14:55:55 H=SJC-efz.ms-acdc.office.com [52.96.3.178] TLS error on connection (send): The specified session has been invalidated for some reason. 14:55:55 send failed: No such file or directory 14:55:55 SMTP(close)>> 14:55:55 Leaving remote_smtp_smarthost transport 14:55:55 LOG: MAIN 14:55:55 ** [email protected] R=smarthost T=remote_smtp_smarthost H=SJC-efz.ms-acdc.office.com [52.96.3.178] X=TLS1.2:ECDHE_RSA_AES_256_GCM_SHA384:256 CV=no DN="C=US,ST=Washington,L=Redmond,O=Microsoft Corporation,CN=outlook.com": SMTP error from remote mail server after pipelined end of data: 530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM [BYAPR04CA0001.namprd04.prod.outlook.com] 14:55:55 cannot use sendfile for body: spoolfile not wireformat 14:55:55 writing data block fd=8 size=624 timeout=0 14:55:55 Exim version 4.92 uid=118 gid=124 pid=1225 D=2a000028 Support for: crypteq iconv() IPv6 GnuTLS move_frozen_messages DANE DKIM DNSSEC Event OCSP PRDR SOCKS TCP_Fast_Open Lookups (built-in): lsearch wildlsearch nwildlsearch iplsearch cdb dbm dbmjz dbmnz dnsdb dsearch nis nis0 passwd Authenticators: cram_md5 plaintext Routers: accept dnslookup ipliteral manualroute queryprogram redirect -- ## List details at https://lists.exim.org/mailman/listinfo/exim-users ## Exim details at http://www.exim.org/ ## Please use the Wiki with this list - http://wiki.exim.org/
