How are you sending the emails exactly? All going through the same mail server or sending to different mail servers?
wwIPStuff only worked with a few protocols. wwSmtp (which is the later version with the same interface) supports a much wider variety of protocols including support for SSL connections for servers like gmail, outlook.com etc.
The error looks like the server send some command that the client doesn't understand and subsequently hangs. If you use wwSmtp especially in .NET mode this is very likely to go away.
http://west-wind.com/webconnection/docs/_s9001zxj2.htm+++ Rick ---
>>Any chance this is an 'AOL' account. In the past (I still think it's true today) wwipstuff seem to have trouble with connecting to AOL. We actually did NOT fix it and the trouble has sort of gone away because all the customers moved off AOL.
>>
>>Johnf
>
>No, not an AOL account. Just some company's email server whatever it is.