Fax Software

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Under normal setup, WinFax will only answer the call when it detects a RING signal from the modem. an outgoing call does not generate a RING message to the modem so WinFax should always ignore any outgoing call.
Do you see WinFax answering the fax with the WinFax answer dialog screen?
Which modem (of the two) is actually answering the outgoing call?

Some modems will answer automatically when they hear a signal on the line, this is not a function of WinFax but the modem itself. I am not familiar with any US Robotics model 5569, if it is a voice modem you may need to determine how to disable the call detection on the modem so it does not “listen” to the line for outgoing calls. If this is an external U.S. Robotics, then DIP switch 5 always overrides the software auto-answer settings, so it will always answer calls.

The preferred solution is not to share devices on the same telephone line.