DirtCreature

Ok, so I’m not sure that helped, but I did the following:

Added this to my theme and set it to 10 seconds:
add_filter(‘cron_request’, ‘my_increase_cron_request_timeout’);
function my_increase_cron_request_timeout($args) {
$args[‘args’][‘timeout’] = 10; // Seconds. Increase as needed.
return $args;
}

Crontrol reported:
There was a problem spawning a call to the WP-Cron system on your site. This means WP-Cron jobs on your site may not work. The problem was:
Operation timed out after 1100 milliseconds (down from 3100)

I then googled that string and found a reference to someone changing their domain name and having the same issue.

After poking around I realized it might be a DNS issue, so I added local lookups for domain (with and without www) to my hosts file and voila, it worked!

I tried to reproduce it by commenting out the hosts file localhost entries, but it continued to work. Since hosts is not cached it’s interesting that it worked.

Anyway, maybe you can add this to your help docs. Some specs:

Windows 2008 R2 / IIS 7.5
WP (latest)
PHP 5.6