problems with connection of sendmail connection to microsoft exchange at Provider

[roland_br]

I use sendmail at a client for many years without problems. Now the provider has changed his mailserver to Microsoft Exchange
my sendmail:

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Version 8.13.8
 Compiled with: DNSMAP HESIOD HES_GETMAILHOST LDAPMAP LOG MAP_REGEX
                MATCHGECOS MILTER MIME7TO8 MIME8TO7 NAMED_BIND NETINET NETINET6
                NETUNIX NEWDB NIS PIPELINING SASLv2 SCANF SOCKETMAP STARTTLS
                TCPWRAPPERS USERDB USE_LDAP_INIT

I uses smtp 587 with the host smtp.office365.com.
I changed the configuration

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define(`SMART_HOST', `smtp.office365.com')dnl
define(`RELAY_MAILER_ARGS', `TCP $h 587')dnl
define(`ESMTP_MAILER_ARGS', `TCP $h 587')dnl
DAEMON_OPTIONS(`Port=smtp,Addr=127.0.0.1, Name=MTA')dnl
DAEMON_OPTIONS(`Port=submission, Name=MSA, M=Ea')dnl
TRUST_AUTH_MECH(`EXTERNAL DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl
define(`confAUTH_MECHANISMS', `EXTERNAL GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl
FEATURE(`authinfo',`hash -o /etc/mail/authinfo/smtp-oleane.db')dn

But as I send an email: mail -s "subject" myemailaddress </tmp/work
I get a logfile that looks like this

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Nov  2 12:41:20 myhostname sendmail[6574]: 3A2BfKRU006574: from=<tbred@myhostname >, size=494, class=0, nrcpts=1, msgid=<202311021141.3A2BfKgr006570@myhostname >, proto=ESMTP, daemon=MTA, relay=localhost.localdomain [127.0.0.1]
Nov  2 12:41:20 myhostname sendmail[6574]: 3A2BfKRU006574: --- 250 2.0.0 3A2BfKRU006574 Message accepted for delivery
Nov  2 12:41:20 myhostname sendmail[6570]: 3A2BfKgr006570: to=cat.roland.br@gmail.com, ctladdr=tbred (501/501), delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=30180, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (3A2BfKRU006574 Message accepted for delivery)
Nov  2 12:41:20 myhostname sendmail[6574]: 3A2BfKRV006574: <-- QUIT
Nov  2 12:41:20 myhostname sendmail[6574]: 3A2BfKRV006574: --- 221 2.0.0 myhostname  closing connection
Nov  2 12:41:20 myhostname sendmail[6576]: 3A2BfKRU006574: SMTP outgoing connect on [192.168.xxx.xxx]
Nov  2 12:41:20 myhostname sendmail[6576]: STARTTLS: ClientCertFile missing
Nov  2 12:41:20 myhostname sendmail[6576]: STARTTLS: ClientKeyFile missing
Nov  2 12:41:20 myhostname sendmail[6576]: STARTTLS: CACertPath missing
Nov  2 12:41:20 myhostname sendmail[6576]: STARTTLS: CACertFile missing
Nov  2 12:41:20 myhostname sendmail[6576]: STARTTLS: CRLFile missing
Nov  2 12:41:20 myhostname sendmail[6576]: STARTTLS=client, init=1
Nov  2 12:41:20 myhostname sendmail[6576]: STARTTLS=client, start=ok
Nov  2 12:41:20 myhostname sendmail[6576]: STARTTLS=client, info: fds=11/10, err=2
Nov  2 12:41:20 myhostname sendmail[6576]: STARTTLS=client, info: fds=11/10, err=2
Nov  2 12:41:20 myhostname sendmail[6576]: STARTTLS=client, get_verify: 20 get_peer: 0x8404558
Nov  2 12:41:20 myhostname sendmail[6576]: STARTTLS=client, relay=smtp.office365.com, version=TLSv1/SSLv3, verify=FAIL, cipher=AES256-SHA, bits=256/256
Nov  2 12:41:20 myhostname sendmail[6576]: STARTTLS=client, cert-subject=/C=US/ST=Washington/L=Redmond/O=Microsoft+20Corporation/CN=outlook.com, cert-issuer=/C=US/O=DigiCert+20Inc/CN=DigiCert+20Cloud+20Services+20CA-1, verifymsg=unable to get local issuer certificate
Nov  2 12:41:20 myhostname sendmail[6576]: STARTTLS=read, info: fds=11/10, err=2
Nov  2 12:41:20 myhostname last message repeated 3 times
Nov  2 12:41:20 myhostname sendmail[6576]: 3A2BfKRU006574: to=<cat.roland.br@gmail.com>, ctladdr=<tbred@myhostname > (501/501), delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=120494, relay=smtp.office365.com [52.98.228.18], dsn=4.0.0, stat=Deferred

As you can see I get in there a message : verifymsg=unable to get local issuer certificate
WHAT does this mean?

[TrevorH]

Nov 2 12:41:20 myhostname sendmail[6576]: 3A2BfKRU006574: SMTP outgoing connect on [192.168.xxx.xxx]
Nov 2 12:41:20 myhostname sendmail[6576]: STARTTLS: ClientCertFile missing
Nov 2 12:41:20 myhostname sendmail[6576]: STARTTLS: ClientKeyFile missing
Nov 2 12:41:20 myhostname sendmail[6576]: STARTTLS: CACertPath missing
Nov 2 12:41:20 myhostname sendmail[6576]: STARTTLS: CACertFile missing
Nov 2 12:41:20 myhostname sendmail[6576]: STARTTLS: CRLFile missing

Start by fixing those.