I had an issue today. My Outlook does not want to connect to office 365 when I setup IE to use SQUID for the proxy. Apparently some of the O365 URLs are resolving up to 25 IP Addresses and depending on the location, some of the connection might get rejected.
By default SQUID only tries the first 10 connections. To change this, edit the squid.conf and add:
forward_max_tries 25
save, restart SQUID instance. Enjoy
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