Verify remote services

SMTP server with telnet

C:\Windows\System32> telnet
Microsoft Telnet> set localecho
Microsoft Telnet> set logfile c:\TelnetTest.txt
Microsoft Telnet> OPEN mail1.fabrikam.com 25
220 mail1.fabrikam.com Microsoft ESMTP MAIL Service ready at Fri, 5 Aug 2016 16:24:41 -0700
EHLO contoso.com
250-mail1.fabrikam.com Hello [172.16.0.5]
250-SIZE 37748736
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-X-ANONYMOUSTLS
250-AUTH NTLM
250-X-EXPS GSSAPI NTLM
250-8BITMIME
250-BINARYMIME
250-CHUNKING
250 XRDST
MAIL FROM: <user@example.com>
250 2.1.0 Sender OK
RCPT TO: <user@example.com> NOTIFY=success,failure
250 2.1.5 Recipient OK
DATA
354 Start mail input; end with <CRLF>.<CRLF>
Subject: test

This is a test message.
.
250 2.6.0 <c89b4fcc-3ad1-4758-a1ab-1e820065d622@mail1.fabrikam.com> [InternalId=5111011082268, Hostname=mail1.fabrikam.com] Queued mail for delivery
QUIT
221 2.0.0 Service closing transmission channel

SMTP server with openssl

To connect using the TLS protocol on port 25, use:

openssl s_client -connect vsp2.example.local:25 -starttls smtp

To connect using the TLS protocol on port 587, use:

openssl s_client -starttls smtp -connect smtp.sendgrid.com:587

To use SSL on port 465:

openssl s_client -connect smtp.sendgrid.com:465