Public Folder Migration – 451 4.4.0 Primary target IP address responded with: “530 5.7.0 Must issue a STARTTLS command first”

Issue –

Migrating Public Folder from Windows Small Business Server 2003 to Windows Small Business Server 2008 fails – Error 451 4.4.0 Primary target IP address responded with: “530 5.7.0 Must issue a STARTTLS command first”

Cause –

TLS authentication is enabled with a certificate on SMTP Virtual Server on the Source Server (SBS 2003)

Steps to Resolve the Issue –

– Open Queue viewer on SBS 2008 Server , you may see all the email related to Public Folders are stuck.
– Open Exchange System Manager on the source server (SBS 2003)
– Open the Properties of Default SMTP Virtual Server
– Click Delivery Tab
– Click on Outbound Security and uncheck TLS encryption and click OK
– After that Click on Access Tab, Under Secure Communication click on Communication and clear   Require Secure Channel and click OK
– Click on Certificate, Click Next button, slect Remove the current certificate and finish the wizard
– Apply the changes and restart SMTP Service from Services Console
– This should fix the issue

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