I have two end users that often email Purchase Orders Internationally...both to China.  On occasion both end users are unable to send their email, they get the long/cryptic Paperless Office error that ends with:

Failed to read beginning of SSL/TLS record.

Failed to read incoming handshake messages (1)

Client handshake failed.

Failed to establish TLS connection.

--SMTP_Connect

Failed to connect to SMTP server.

Failed.

In both cases, if they wait a couple of minutes and try again it tends to work.  Anyone else run into this and anyone have any tips?

Both clients are currently running Sage 100 2018 and both run their email through outlook.office365.com.

Thanks!