I have the paid version of version 6. I have the settings detect new network automatically. Also under network rules make sure any program that needs to use your LAN/Internet has at least custom access.
There is no setting in outpost free that allows you to automatically connect to networks that I have been able to find.
Sorry couldn't help more. Hopefully someone with the free version will respond with more useful advice.
bamaman66, I would look elsewhere for a free firewall, as OP free has not been supported by the developer for quite some time. In fact, they are concentrating their efforts primarily on the newest version 6 (trial).
I agree with wat0114. The free Outpost gave my computer the BSOD when I tried it a few months back. There are a ton of good free firewalls that are offered all over. Don't waste your time with Outpost free. Just do a search for free firewalls or just check out this thread for what others are using- https://www.wilderssecurity.com/showthread.php?t=189927 You can see from the poll results that of the 92 votes, zero are using Outpost free.
You might want to look at this post from the Outpost forum: http://www.outpostfirewall.com/forum/showthread.php?t=15745
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