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5.7.57 smtp error when sending email from one software package only

We recently moved to a hybrid exchange/office 365. We had various copiers and software packages that sent emails out and were able to get all of them working using email relay EXCEPT for one package. We can't get this one package to consistently work no matter what we do. They have 3 options for mode: unauthenticated, authenticated (specific) and authenticated (windows). If I use the Windows option, emails work for one staff member only (the person whose email address and password were used) but won't work for anyone else. If I use any other options I get error 5.7.57. Port 587 is being used and there is an option to enable SSL and enable TLS. It only works for one user if the enable SSL is checked. I've tried using a generic login and password and that won't work either. I've tried every combination I could try and in general get the following error: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 SMTP; client was not authenticated to send anonymous mail during Mail from [YTXPR0101CA0006.canprd01.prod.outlook.com]. I don't under why relay works 4 copiers and 8 other packages and not this one. The vendor said it is an issue with email so it isn't their problem.

Any ideas?

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timgreen7077

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cindyfiller

ASKER

I've used that article or something similar. Option 1 doesn't work - that's the one I've worked with most. Option 2 doesn't apply because the emails go out to external customers. Right now option 3 can't be used because all of our DNS records point to Proofpoint, our external spam filter. I'm not sure if that is causing some of the issues... I'll read through it more closely tomorrow and see if there is anything that will help. Thanks for replying!

cindyfiller

ASKER

We never could get this to work and decided to replace the package instead. I'm giving Tim the credit because I do believe his solution would work for most of these issues.