from the netlog snippet in the doc, it looks like
1. UrlRequest does an http transaction, which fails with HTTP/1.1 401 Unauthorized.
2. UrlRequest does another http transaction with "Authorization: Negotiate ..." 
which fails with 
+HTTP_TRANSACTION_READ_HEADERS [dt=11]
t=38 [st=38] HTTP_STREAM_PARSER_READ_HEADERS [dt=11]
--> net_error = -103 (ERR_CONNECTION_ABORTED)
t=49 [st=49] HTTP_TRANSACTION_RESTART_AFTER_ERROR
--> net_error = -103 (ERR_CONNECTION_ABORTED)
t=49 [st=49] -HTTP_TRANSACTION_READ_HEADERS
t=49 [st=49] +HTTP_STREAM_REQUEST [dt=15]
t=49 [st=49] HTTP_STREAM_JOB_CONTROLLER_BOUND
--> source_dependency = 14531 (HTTP_STREAM_JOB_CONTROLLER)
t=64 [st=64] HTTP_STREAM_REQUEST_BOUND_TO_JOB

--> source_dependency = 14532 (HTTP_STREAM_JOB)
t=64 [st=64] -HTTP_STREAM_REQUEST
t=64 [st=64] AUTH_SERVER [dt=0]
t=64 [st=64] -URL_REQUEST_START_JOB
--> net_error = -9 (ERR_UNEXPECTED)
t=64 [st=64] URL_REQUEST_DELEGATE_RESPONSE_STARTED [dt=0]
t=65 [st=65] -REQUEST_ALIVE
--> net_error = -9 (ERR_UNEXPECTED)


So it seems like the server is aborting the 2nd connection which is trying to do http auth. That sounds like a server side problem.

I don't know why that ends up with the UrlRequest failing with ERR_UNEXPECTED though.

clarification: When I said "2nd connection" above, I should have said "2nd request". It may have been over the same connection (not entirely clear to me just from the snippet).

manesh.manickam@ Thanks for the issue.

This issue seems to be out of scope of triaging at TE end. 
Hence adding 'TE-NeedsTriageHelp' label and requesting 'Internals>Network>Auth' team to look into the issue and help in further triaging.

Thanks..

Looks like a state machine issue.