NSURLRequest Timing out without making connection to server - swift

Question

I have an application written in swift that communicated with my server using PHP. Throughout my testing the app has worked perfectly until I began testing on multiple devices simultaneously. When i try to load both devices at the same time it will sporadically (not 100%) create this timeout:
Error Domain=NSURLErrorDomain Code=-1001 "The request timed out." UserInfo=
{NSUnderlyingError=0x127ea9fb0 {Error Domain=kCFErrorDomainCFNetwork Code=-1001 "(null)" UserInfo={_kCFStreamErrorCodeKey=-2102, _kCFStreamErrorDomainKey=4}}, NSErrorFailingURLStringKey=https://myhttpsdomain/my_page.php, NSErrorFailingURLKey=https://myhttpsdomain/my_page.php, _kCFStreamErrorDomainKey=4, _kCFStreamErrorCodeKey=-2102, NSLocalizedDescription=The request timed out.}
Error with domain:https://myhttpsdomain/my_page.php
It creates this timer without ever making the connection to the server. Once the issue has been triggered all web requests from that device will create the error for a few minutes.
I am using a basic let task = session.dataTaskWithRequest to send post requests to my server.
To decide whether the server connection was made or not the first line in my php file is error_log("Page has been called"); And this line isn't even printing.

Answer 1

This is probably one of the following:
a DNS problem
a routing problem/network problem
a server configuration issue
First, check the server logs and see if the request suddenly appears in the logs whenever the client gives up on the connection. If so, you'll need a packet trace to know for sure, but chances are, your PHP script is wedging forever before it sends headers or the server is otherwise misconfigured in some way.
If not, then sniff the network and see if it is even sending out a request. And make sure that both devices can ping each other.