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Stephanie SnakovskyStephanie Snakovsky 

Why do I have to login when going from SalesForce to Trailhead to Developers?

Josh SimnittJosh Simnitt

I agree, that's a constant annoyance.  

Maybe Salesforce is afraid you might be logged into different orgs and don't want to automatically determine which one you would like to be logged in under? 
Nilotpal RoyNilotpal Roy
Hi,
You can connect your Developer Edition to Trailhead. Chose your own org in trailhead challenge.
Thanks,
Nilotpal Roy