I removed your pdf as it contains your credentials (base64 which may be easily decrypted !); but likely your file does not yet downloaded by somebody.
It seems office365 smtp expect ehlo command before auth command (see https://support.sugarcrm.com/Knowledge_Base/Email/Testing_Outbound_Email_Using_Command_Line/) and does not support plain login. so you have to sent password and login in a single command.
So first encrypt alone login and password
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/usr/bin/echo -n "yourlogin" | /usr/bin/openssl enc -base64 -A
/usr/bin/echo -n "yourpassword" | /usr/bin/openssl enc -base64 -A
Then run the openssl command
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openssl s_client -starttls smtp -connect smtp.office365.com:587
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ehlo
if you get "334 VXNlcm5hbWU6" you can send first your login (encrypted previously) and on the output "334 UGFzc3dvcmQ6" send your encrypted password.
So you should to be accepted (code 235). In all case I need to update the mail script... :whistle