Can anyone explain why I can only initiate the VPN from one side?

I am creating a site to site VPN between two Cisco ASA's. The problem I
am running into, and can't answer, is that if I ping from the remote
site, back to the central site, the ping fails (I mean that it fails over the VPN, as the IPSec tunnel doesn't even try phase1). The second I start a
ping from the central site towards the remote site, the VPN fires up and
everything works perfectly. I can ping to and from either side. On a high level overview, what could cause this weird symptom? I am runnning it between a 5550, and a 5585. The only other time I've seen this problem is on a dodgey version of code.

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