SSRS – Validating Smart Host – Using Mozilla Thunderbird

Background

A few posts ago, we provisioned a Smart Host.

Let us quickly test it out.

 

Lineage

Here are other posts in this multi-series:

  1. SSRS – Setting up Smart Host
    Link

Scenario

To make sure that we understand the specificity of Microsoft’s Office 365 SMTP service, we will install a free, durable email client; specifically Mozilla Thunderbird.

 

Wireshark

Filter

  1. tcp.port == 25 || tcp.port == 465 || tcp.port == 587

Mozilla Thunderbird

Download

Download Mozilla Thunderbird from here.

Installation

Installation is straightforward.

Configuration

Images

Session – 1

Configuration
SMTP Server Settings

 

Output
Netstat

WireShark

 

Session – 2

Configuration
SMTP Server Settings

Output
Netstat

WireShark

WireShark – SMTP ( Destination Port 587 ) – 01
WireShark – Explanation
  1. Connection to SMTP Host
WireShark – SMTP ( Destination Port 587 ) – 02

WireShark – Explanation
  1. Reply from SMTP Host

 

Session – 3

Configuration
SMTP Server Settings

WireShark

WireShark – Explanation
  1. We see a fuller conversation

 

Item Port :- 465 /
Connection :- SSL/TLS
Port :- 587 /
Connection Start :- SSL/TLS
Port :- 587 /
Connection Start :- STARTSSL
Server Name smtp.office365.com smtp.office365.com smtp.office365.com
Port 465 587 587
Connection Security SSL/TLS SSL/TLS STARTTLS
Authentication Password Normal Password Normal Password Normal Password
Results SYN/SENT  Truncated Conversation  Full Conversation

 

Network Ports

  1. Port :- 25
    • SMTP
      • Server to Server email
        • Message relay port
      • (-)
        • Not Authenticated
        • Blocked by a lot of firewall
  2. Port :- 465
    • SMTP
      • (-)
        • Not widely adopted
  3. Port 587
    • SMTP
      • Mail Submission Port
      •  (+)
        • Authenticated emails

 

References

  1. Microsoft
    • Office
      • Support
        • POP and IMAP settings for Outlook Office 365 for business
          Link
        • How to set up a multifunction device or application to send email using Office 365
          Link
    • technet
      • blogs.technet.com
        • Andrew Stobart – Useful Wireshark Filters for Mail Flow Troubleshooting
          Link
  2. Mozilla.Org
    • Mozilla Support
      • cannot send mail. Connected to smtp.office365.com but times out.
        Link
  3. Stanford University
    • Stanford | University IT
      • How to Configure Thunderbird for Office 365 Using IMAP
        Link
  4. StackOverflow
    • Network Ports
      • What is the difference between ports 465 and 587?
        Link
  5. JSCAPE
    • Managed File Transfer and Network Solutions
      • John Carl Villanueva
        • Still Confused With SMTP Ports? Read This
          Link
  6. FastMail
    • SSL vs TLS vs STARTTLS
      Link

 

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