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How to troubleshoot network issue with Cisco ASA, Router, Wireless AP, and Switch

Posted on 2013-12-09
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Last Modified: 2013-12-21
Hello experts - I recently assumed additional responsibilities at work which include all switching and routing.  I'm not an expert (yet) so could use some help in getting started troubleshooting a particular issue.  I am attempting to setup a private wireless network that will connect Apple devices to my LAN for access to email and RDP.  Its 90% there, the only remaining issue is that users on the wireless network can't access https sites which run on it.  Going out to the internet works fine with https, its just internally where the sites won't load.  The configuration is setup where the wireless access points are connected to a 2504 controller.  This is attached to a 4510 switch as is the 2811 router (gateway) and 5510 ASA (firewall).  In this case I believe the problem is on the router or switch since requests for internal sites shouldn't be routed to the ASA.  

That is where I'm stuck.  I am not certain how best to troubleshoot access issues like this between devices.  I would appreciate any tips or advice to get me going, thanks!
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Question by:First Last
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by:Henk van Achterberg
ID: 39706721
the problem is that you try to visit the external IP addresses that reside on the outside interface of the ASA.

You can do two things:

1. configure the DNS server to return the inside IP adresses of the server instead of the external IP's
2. NAT the external IP addresses FROM the inside TO the inside (and change the source IP address to the interface).
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by:First Last
ID: 39706732
Hi henkva - perhaps I am misunderstanding your reply but I don't think it applies in this case.  I am already on the inside LAN connected to the wireless network.  I can ping, RDP, an access internal sites using HTTP but not HTTPS.  Everything out to the internet works fine as well.  So in my case these sites don't exist outside the LAN, they are only accessible internally.
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by:atrevido
ID: 39708889
can you post a network drawing so we can see how things are connected, it can be hand drawn and scanned if you don't have time to do a traditional Visio.  

Also, post a show run from your router, scrub the public ip addresses though
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by:First Last
ID: 39708928
Ok, that will take a little time, I'll work on it today.
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First Last earned 0 total points
ID: 39721487
I wound up working with Cisco on this and determined its not a Cisco issue but a problem with VMware networking.
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by:First Last
ID: 39733388
Found own answer
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