Problems using wildcard SSL certificate with 2008 TS Gateway

i had working in test environment. have 1 2008 terminal server , 1 2008 iis server running ts gateway. had self-signed certificate proper dns name (ts.domain.com) , working fine. purchased wildcard ssl certificate , assigned ts gateway , it's not retaining configuration. whenever try connect error message "this computer can't connect remote computer because no certificate configured use @ terminal services gateway server. contact network administrator assistance."

so here couple oddities can't make heads or tails of, may troubleshooting process:

1) have installed wildcard ssl certificate default website on ts gateway server. that's working properly.

2) in ts gateway manager -> <server> properties -> ssl certificate tab it's set "select existing certificate ssl encryption" yet nothing displayed. click on browse certificates , select wildcard certificate installed on server. reflected on screen , looks good. hit apply , ok. @ point try access remote desktop ts web access same error message before.

3) if restart "terminal services gateway" service, undoes configuration change made in #2 above. shows no ssl certificate selected.

4) found in system event log, apply changes in #2 above, following 2 events alternating 3-4 times:

warning - source: httpevent - event id 15300
ssl certificate settings deleted port : 192.168.100.140:443 .

warning - source: httpevent - event id 15301
ssl certificate settings created admin process port : 192.168.100.140:443 .


what going on here?

yes i've seen article , no of questions. there's nothing wrong the certificate. it's typical wildcard certificate purchased thawte.

i've solved own problem. after bit of testing able consistently reproduce , fix problem. boils down having multiple ip addresses on network adapter, , not using "all unassigned" in http/https bindings in iis. web server multiple websites, of course have multiple ip addresses on box. i have 3 ip addresses on server. default website bound specific ip address, , not "all unassigned". https binding configured same specific address. when configured way, reason when select certificate within ts gateway manager, doesn't work. if restart terminal services gateway service, blows away assigned certificate within tsgm.

to fix issue went iis, modified https binding default website pointing * (all unassigned) opposed specific ip address. once made change, went tsgm , selected same certificate. time worked. restarted service , rebooted server on safe side. everything's working properly.

sounds bug in ts gateway me.

thanks anyways.

Windows Server  >  Remote Desktop Services (Terminal Services)