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Published 20 hours ago • verified publisher icon mogaal

Sendemail TLS Problem with Exchange 2019

Open Manuel1948 opened this issue 4 years ago • 2 comments 

C:\scripts>sendemail.exe -t [email protected] -f [email protected] -u test -m test -s xxx.xx:587 -xu xxx -xp ppp -v -v -o tls=yes
Jun 09 23:19:14 i5-3470s sendemail.exe[23352]: DEBUG => Connecting to xxx.xx:587
Jun 09 23:19:14 i5-3470s sendemail.exe[23352]: DEBUG => My IP address is: 192.168.138.48
Jun 09 23:19:14 i5-3470s sendemail.exe[23352]: DEBUG => evalSMTPresponse() - Found SMTP success code: 220
Jun 09 23:19:14 i5-3470s sendemail.exe[23352]: SUCCESS => Received:     220 xxx.xx Microsoft ESMTP MAIL Service ready at Tue, 9 Jun 2020 23:19:12 +0200
Jun 09 23:19:14 i5-3470s sendemail.exe[23352]: INFO => Sending:         EHLO i5-3470s
Jun 09 23:19:14 i5-3470s sendemail.exe[23352]: DEBUG => evalSMTPresponse() - Found SMTP success code: 250
Jun 09 23:19:14 i5-3470s sendemail.exe[23352]: SUCCESS => Received:     250-xxx.xx Hello [IP-hidden], 250-SIZE 37748736, 250-PIPELINING, 250-DSN, 250-ENHANCEDSTATUSCODES, 250-STARTTLS, 250-AUTH GSSAPI NTLM, 250-8BITMIME, 250-BINARYMIME, 250-CHUNKING, 250 SMTPUTF8
Jun 09 23:19:14 i5-3470s sendemail.exe[23352]: DEBUG => The remote SMTP server supports TLS :)
Jun 09 23:19:14 i5-3470s sendemail.exe[23352]: DEBUG => Starting TLS
Jun 09 23:19:14 i5-3470s sendemail.exe[23352]: INFO => Sending:         STARTTLS
Jun 09 23:19:14 i5-3470s sendemail.exe[23352]: DEBUG => evalSMTPresponse() - Found SMTP success code: 220
Jun 09 23:19:14 i5-3470s sendemail.exe[23352]: SUCCESS => Received:     220 2.0.0 SMTP server ready
Jun 09 23:19:15 i5-3470s sendemail.exe[23352]: ERROR => **TLS setup failed: SSL connect attempt failed because of handshake problemserror:00000000:lib(0):func(0):reason(0)**

Everytime excatly this error with sendemail, why and what is the error trying to say?

Manuel1948 avatar Jun 09 '20 21:06 Manuel1948

Any solution you got for thiis

panguluriravikanth avatar Oct 29 '21 03:10 panguluriravikanth

Check out this unmerged Pull Request: https://github.com/mogaal/sendemail/pull/22/commits/dd0ec96aed8af3ff9c069cec222551f9b5d8f601

I did the Change for myself in my code, and it worked for me.

levi-jcbs avatar Oct 29 '21 11:10 levi-jcbs

This worked for me

  1. uninstall sendemail
  2. apt install apt-transport-https libio-socket-inet6-perl -y
  3. curl 'http://ftp.cn.debian.org/debian/pool/main/s/sendemail/sendemail_1.56-5.2~bpo12+1_all.deb' -O
  4. dpkg -i sendemail_1.56-5.2~bpo12+1_all.deb

abhi-io avatar Jun 12 '24 08:06 abhi-io

This worked for me

  1. uninstall sendemail
  2. apt install apt-transport-https libio-socket-inet6-perl -y
  3. curl 'http://ftp.cn.debian.org/debian/pool/main/s/sendemail/sendemail_1.56-5.2~bpo12+1_all.deb' -O
  4. dpkg -i sendemail_1.56-5.2~bpo12+1_all.deb

not only that the solution is coming 4 years too late, it is also not helpful for a Windows machine, which you can see clearly in the log from the path and executable 🤣

thank you for trying 😅

Manuel1948 avatar Jun 12 '24 09:06 Manuel1948