Check IMAP and POP with OpenSSL

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IMAP

Gmail

[1][2][3][4]Currently I have little understanding as to what I am looking at. More specifically I do not know what the "-crlf" in openssl does or

[5] The second incantation is typically used for Microsoft Exchange servers. Note the -crlf option, which tells s_client to send \r\n line endings. If the wrong line ending is used for a server, the symptom is that the server will not respond to any commands. It will only sit there and wait for further input, while you are staring at a blank responses or blank lines in your telnet session.

openssl s_client -connect imap.gmail.com:993 -crlf
a login <username> <password>
a select inbox
a FETCH 1 (FLAGS BODY[HEADER.FIELDS (subject)])
a store 1 +flags /deleted
a expunge
a close
a logout

Office365

openssl s_client -connect outlook.office365.com:993 -crlf
a login <username> <password>
a select inbox
a FETCH 1 (FLAGS BODY[HEADER.FIELDS (subject)])
a store 1 +flags /deleted
a expunge
a close
a logout
QUIT

POP3

Office365

[6]

openssl s_client -connect outlook.office365.com:995 -crlf 
USER user@yourdamin.com
PASS yourpassword
LIST
STAT
RETR message#
QUIT

SMTP

Office365

[7]

openssl s_client -starttls smtp -connect smtp.office365.com:587 -crlf
250 CHUNKING
ehlo
250-DM5PR04CA0045.outlook.office365.com Hello [64.191.109.50]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-AUTH LOGIN
250-8BITMIME
250-BINARYMIME
250 CHUNKING
auth login 
334 VXNlcm5hbWU6