How to diagnose connection timeouts when connecting to a WiFi hotspot
Don't have the solution but have interesting observation!!

My WiFi scan shows the SSID that I want to connect to



and in Terminal the Airport -s shows same SSID



I was monitoring the Console during the event.



The Associate event still shows the Correct SSID

&lt;airportd[535]&gt; associate: INFO: airportd associate: network=&lt;CWNetwork: 0x7fec12802ce0&gt; [ssid=Eurona900850808-81, bssid=02:0c:42:39:95:94, security=Open, rssi=-80, channel=&lt;CWChannel: 0x7fec12802cf0&gt; [channelNumber=7(2GHz), channelWidth={20MHz}], ibss=0], is8021X=0, remember=1


After few lines of other WiFi activity this comes up:

&lt;kernel&gt; Searching for networks with ssid Eurona900850808-8


WAIT: where did the last digit go, it supposed to be the Eurona900850808-81, but it shows Eurona900850808-8

Here is the rest from the Console:

Fri Sep 13 23:22:55.92  &lt;kernel&gt; Searching for networks with ssid Eurona900850808-8
Fri Sep 13 23:22:57.488 &lt;kernel&gt; No networks found. Please check if the network exists and is in range
Fri Sep 13 23:22:57.488 &lt;airportd[535]&gt; _WiFiMT_LogAssocTimeoutFail: MT** Assoc Timeout
Fri Sep 13 23:22:57.488 &lt;airportd[535]&gt; associate: Apple80211Associate2() failed with error -3905


Clearly the SSID lost the last digit somewhere in the process, and that leads to the Famous Timeout Error at least in my case.

While Apple provides great tools to analyze the WiFi, it is lacking bit more descriptive Error messages, like in my case saying there is no such network available since it clearly knows that in the Console report.