When authentication times out that is one thing, but when it just fails like below Asterisk by default will not re-register until you the admin reload the sip or asterisk server:

voipserver*CLI> sip show registry
Host                           dnsmgr Username       Refresh State                Reg.Time                
remote.voipservice.com:5060          N      151113             105 No Authentication    Sat, 25 Apr 2020 11:20:08
1 SIP registrations.

Now reload and it will re-register

voipserver*CLI> sip reload
voipserver*CLI> sip show registry
Host                           dnsmgr Username       Refresh State                Reg.Time                
remote.voipservice.com:5060          N      151113             105 Registered           Sat, 25 Apr 2020 12:22:09
1 SIP registrations.
 

How do we fix this so it retries when authentication fails?

under /etc/asterisk/sip.conf where you have your trunk peer add this:

register_retry_403=yes
 

Then restart asterisk or reload it and the above setting should sort it out and make Asterisk keep retrying

Note that the setting registerattempts=0 (which is unlimited retries) does not fix the problem shown above, but only register_retry_403=yes fixes it.

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