WordPress Plugin Upgrade Timeout Issue

If you experiencing failure to update plugins bigger than 2mb i.e Jetpack, you may want to look at Core Control plugin

Core control plugin allows you to select and disable problematic HTTP transport control.
In our case, we prefer cURL method because its is more reliable than PHP Streams.  Here is how to configure.

Core Control

Then Select External HTTP  Access

Then you can try update your plugins again.