your-apache-tomcat-ip:

Michael,
Sorry I could not answer before.I read your note and I think this is mostly 
off-topic. I am not sure I understand what you want to do with stunnel in this 
configuration. But l will try an educated guess:
1. Keep in mind that Stunnel is mostly used for securing services that do not 
support TLS natively.I haven't worked with tomcat + ISS, but I have experience 
with tomcat + Apache httpd
2. It looks like you already have your IIS servers configured to serve web 
requests with TLS on port 443, and since you are trying to insert an stunnel 
client between IIS and tomcat AJP port (9009 or 8009), I guess you are trying 
to encrypt the AJP trafic. It doesn't make much sense to encrypt local traffic, 
so I assume your apache tomcat is running on different host than your IIS. Is 
this correct? 

3. If I am right on 2, you need to run an stunnel in your IIS host and another 
stunnel in your tomcat host. 

In your IIS host, you configure stunnel like this:
[client]accept = localhost:9009connect = your-apache-tomcat-ip:10009 (or 
another free port)client = yes
In your tomcat host, you configure stunnel like this:
[server]accept = your-apache-tomcat-ip:10009 (same port as connect in client)
connect = localhost:9009 (or another free port)client = no
Do you see the tunnel? Note that your isapi filter in IIS should also reference 
localhost and port 9009.

Hope this helps.
Regards,Jose

      From: J. Michael Drew <[email protected]>
 To: 'Jose Alf.' <[email protected]> 
Cc: [email protected]
 Sent: Monday, June 20, 2016 6:00 PM
 Subject: RE: [stunnel-users] FW: Stunnel with IIS8 on server 2012 64 bit
   
.Jose,  I appreciate your patience.   Internet -  Clients : 443 ->  : 
https://website.company.com/website/  ________Firewall___________  
Web\Presentation Layer  2 Win 2012 Webservers (443) not currently connected to 
the production LB, application needs to work before connecting to LB. This 
configuration is first time on 64 bit OS… Win 2012.IIS 8 running Jakarta ISAPI 
Filter\Stunnel to redirect 9001 to 9009:  _________Firewall\App 
Layer________Port 9009  Connects to App server running Apache      Application 
is working as expected as long as I am logged in to the IIS 8 server. I can 
telnet to the APP layer over 9009 and I can reach these websites externally as 
expected. Firewalls are good.  Please let me know any other information you 
need.  Thank you again,  Michael         From: Jose Alf. 
[mailto:[email protected]] 
Sent: Monday, June 20, 2016 4:32 PM
To: J. Michael Drew
Subject: Re: [stunnel-users] FW: Stunnel with IIS8 on server 2012 64 bit  
Michael,  Please take this in constructive way. I am trying to help, but it 
looks like you need to do some reading and homework. Please check 
http://catb.org/~esr/faqs/smart-questions.html  I suggest you draw a picture of 
your environment and explain well what you're trying to achieve.  Show your 
client, your backend server, your stunnel server, include the IPs and ports 
they're listening to and everything should be easier. Don't forget any 
firewalls thay may be in the way.  Regards,Jose.  From: J. Michael Drew 
<[email protected]>
To: 'Jose Alf.' <[email protected]> 
Sent: Monday, June 20, 2016 1:00 PM
Subject: RE: [stunnel-users] FW: Stunnel with IIS8 on server 2012 64 bit  Hi 
Jose, I made the changes you suggested, but I am still getting the same 
behavior. My external address is: https://website.company.com/website I am not 
adding any ports to the address. Thanks so much for your help! Michael From: 
Jose Alf. [mailto:[email protected]] 
Sent: Monday, June 20, 2016 12:10 PM
To: J. Michael Drew; [email protected]
Subject: Re: [stunnel-users] FW: Stunnel with IIS8 on server 2012 64 bit 
Michael,  I guess what you want to do is to be able to connect to your internal 
Webserver via your Win2012 stunnel proxy using a URL like:  
https://yourwin2012dnsname:9001/  if that is correct, I suggest to adjust your 
configuration as follows:  1. Your stunnel mode must be server, not client. So 
adjust your service stanza as follows:  
[CLI9F529A0A]accept=9001connect=10.xxx.xxx.xxx:9009client=no 2. In your current 
configuration stunnel is listening only in the localhost ipv4 address 
(127.0.0.1). Therefore, you can only connect when you are logged on the server, 
you can't connect from a remote client.  Hope this helps you clarify what's 
going on.  Regards,Jose From: J. Michael Drew [mailto:[email protected]] 
Sent: Monday, June 20, 2016 9:54 AM
To: 'Josealf.rm'
Subject: RE: [stunnel-users] Stunnel with IIS8 on server 2012 64 bit Jose, Once 
logged in to the server I can open a browser on the server and connect through 
https://localhost/website and I can log in to the site externally as expected. 
Here are the log files from IIS and stunnel where stunnel is running as a 
service on the Windows 2012 server: When I am not logged in to the server it 
fails: #Software: Microsoft Internet Information Services 8.5#Version: 
1.0#Date: 2016-06-20 00:30:21#Fields: date time s-ip cs-method cs-uri-stem 
cs-uri-query s-port cs-username c-ip cs(User-Agent) cs(Referer) sc-status 
sc-substatus sc-win32-status time-taken2016-06-20 00:30:21 159.xxx.xxx.xxx HEAD 
/ - 443 - 190.xxx.xxx.xxx - - 200 0 0 1218#Software: Microsoft Internet 
Information Services 8.5#Version: 1.0#Date: 2016-06-20 05:41:01#Fields: date 
time s-ip cs-method cs-uri-stem cs-uri-query s-port cs-username c-ip 
cs(User-Agent) cs(Referer) sc-status sc-substatus sc-win32-status 
time-taken2016-06-20 05:41:01 10.xxx.xxx.xxx OPTIONS 
/C$/windows/system32/NTDLL.DLL - 80 - 159.xxx.xxx.xxx 
Microsoft-WebDAV-MiniRedir/6.1.7601 - 200 0 0 5002016-06-20 05:41:01 
10.xxx.xxx.xxx PROPFIND /C$/windows/system32/NTDLL.DLL - 80 - 159.xxx.xxx.xxx 
Microsoft-WebDAV-MiniRedir/6.1.7601 - 404 0 2 462016-06-20 05:41:01 
10.xxx.xxx.xxx PROPFIND /C$/windows/system32 - 80 - 159.xxx.xxx.xxx 
Microsoft-WebDAV-MiniRedir/6.1.7601 - 404 0 2 2182016-06-20 05:41:16 
10.xxx.xxx.xxx PROPFIND 
/patch-{682810b5-36dc-4e5d-81dd-6c02cd8f445b}-patchtoolsd.exe - 80 - 
159.82.156.241 Microsoft-WebDAV-MiniRedir/6.1.7601 - 404 0 64 622016-06-20 
05:41:27 10.xxx.xxx.xxx PROPFIND /N$cl64.exe - 80 - 159.xxx.xxx.xxx 1 
Microsoft-WebDAV-MiniRedir/6.1.7601 - 404 0 2 622016-06-20 05:41:27 
10.xxx.xxx.xxx PROPFIND /C$rome.dll - 80 - 159.xxx.xxx.xxx 
Microsoft-WebDAV-MiniRedir/6.1.7601 - 404 0 2 296 Stunell.conf: cert = 
extwebsvr_ver.pem ; Some performance tuningsocket = l:TCP_NODELAY=1socket = 
r:TCP_NODELAY=1 ; Peer Authenticationverify = 2CAfile = extwebsvr_root.pem ; 
Debug mode - useful for troubleshootingdebug = 7output = stunnel.log  ; Client 
modeclient = yes ; Setup tunnels to each EMS node 
[CLIxxxxxxxx)]accept=127.0.0.1:9001connect=10.xxx.xxx.xxx:9009 Stunnel.log: 
2016.06.20 09:17:39 LOG7[main]: No limit detected for the number of 
clients2016.06.20 09:17:39 LOG5[main]: stunnel 5.27 on x86-pc-msvc-1500 
platform2016.06.20 09:17:39 LOG5[main]: Compiled/running with OpenSSL 
1.0.2e-fips 3 Dec 20152016.06.20 09:17:39 LOG5[main]: Threading:WIN32 
Sockets:SELECT,IPv6 TLS:ENGINE,FIPS,OCSP,PSK,SNI2016.06.20 09:17:39 LOG7[main]: 
errno: (*_errno())2016.06.20 09:17:39 LOG5[main]: Reading configuration from 
file stunnel.conf2016.06.20 09:17:39 LOG7[ui]: GUI message loop 
initialized2016.06.20 09:17:39 LOG7[cron]: Cron thread initialized2016.06.20 
09:17:39 LOG5[main]: UTF-8 byte order mark detected2016.06.20 09:17:39 
LOG6[main]: Initializing service [CLI9F529A0A]2016.06.20 09:17:39 LOG6[main]: 
Loading certificate from file: extwebsvr_ver.pem2016.06.20 09:17:39 LOG6[main]: 
Certificate loaded from file: extwebsvr_ver.pem2016.06.20 09:17:39 LOG6[main]: 
Loading private key from file: extwebsvr_ver.pem2016.06.20 09:17:39 LOG6[main]: 
Private key loaded from file: extwebsvr_ver.pem2016.06.20 09:17:39 LOG7[main]: 
Private key check succeeded2016.06.20 09:17:39 LOG4[main]: Service 
[CLIxxxxxxxx] uses "verify = 2" without subject checks2016.06.20 09:17:39 
LOG4[main]: Use "checkHost" or "checkIP" to restrict trusted 
certificates2016.06.20 09:17:39 LOG7[main]: SSL options: 0x03000004 
(+0x03000000, -0x00000000)2016.06.20 09:17:39 LOG5[main]: Configuration 
successful Thanks for your help, Michael    From: Josealf.rm 
[mailto:[email protected]] 
Sent: Monday, June 20, 2016 8:01 AM
To: J. Michael Drew
Cc: [email protected]
Subject: Re: [stunnel-users] Stunnel with IIS8 on server 2012 64 bit Michael, 
Is your stunnel running as a service?Please post sanitized logs and 
configuration for a better diagnostic ...

Regards Jose
El 20 jun 2016, a las 6:39, J. Michael Drew <[email protected]> escribió:
Hi, I have a website on IIS8 and am using stunnel to forward requests over 9009 
inside to my application server.  When I log in to the IIS server and stay 
logged in everything works as expected. When I log off the IIS 8 web server my 
site is unreachable with a “service is unavailable”. Can someone help me? 
Sincere thanks, Michael

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