Slow ActiveSync?
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We just implemented a pfsense box serving 600-700 users with about 15 vlan interfaces configured on the pfsense box. We're using Squid and DansGuardian for content filtering, but only on port 80. We are doing some throttling via the limiter for each interface as well.
Everything is working well, but we've noticed that users with smartphones behind the pfsense box (Myself included) noticing extremely slow activesync push notifications of new messages. The Exchange box itself is hosted elsewhere on the internet, so it's not a local NAT reflection issue or anything.
Anyone ever run into a similar issue? We've checked all that we can and it just seems very intermittent from behind the pfsense box, but from nowhere else. Tossing myself in front of the pfsense box (Same internet connection) things run as expected with the smartphone.
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As I recall, Activesync runs off HTTP & HTTPS. You might want to add your Exchange server IP/ domain to the cache bypass list for Squid and try again. Adding to the whitelist should help too.