I've filed a bug report at bugs.php.net[1] and linked to this bug
report.

I'll ask for more details about this specific server. I tried a bunch of
other sites with a similar setup but can't reproduce it elsewhere yet.
Maybe there is a firewall rule that is blocking packets? Seems strange
that it would work for php 5.2.10 but not 5.3 though. Hopefully the php
folks can provide some insight as to what changed between those
versions. Nothing obvious (to me at least) jumps out on the
changelog[2]:

Fixed bug #50832 (HTTP fopen wrapper does not support passwordless HTTP 
authentication). (Jani)
Fixed bug #50791 (Compile failure: Bad logic in defining fopencookie 
emulation). (Jani)
Fixed bug #48637 ("file" fopen wrapper is overwritten when using 
--with-curlwrappers). (Jani)
Fixed bug #43510 (stream_get_meta_data() does not return same mode as used in 
fopen). (Jani)
Optimized require_once() and include_once() by eliminating fopen(3) on second 
usage. (Dmitry)
Added 'n' flag to fopen to allow passing O_NONBLOCK to the underlying open(2) 
system call. (Mikko)
Added "ignore_errors" option to http fopen wrapper. (David Zulke, Sara)

Scott
--------
[1] http://bugs.php.net/bug.php?id=52106
[2] http://php.net/ChangeLog-5.php

** Bug watch added: bugs.php.net/ #52106
   http://bugs.php.net/bug.php?id=52106

-- 
fopen fails on some SSL urls
https://bugs.launchpad.net/bugs/592442
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