Let’s Encrypt & IIS as reverse proxy with Certify the Web

After I have been running Teamcity and Octopus Deploy behind a Microsoft IIS without a certificate for some years I decided to give it a go again.

The reason it's behind using a reverse proxy:

  • Teamcity is hosted on a Tomcat HTTP Server and Octopus Deploy is self hosted. Both running on a custom port.
  • Limited in the number of external IP's ... the Teamcity and Octopus Server is running on a different host(could be run on the same host since they are running on different post).

Octopus Deploy does Have built-in support for Let's Encrypt but that forces me to run it on post 80, which of the above reasons is not possible.


  1. Install Certify
  2. Edit web.config
  3. Run Certify for the selected sites.

Step 1

Go to Certify The Web and download the latest release. You can find the src for the project on GitHub Certify The Web - SSL Manager

Step 2

Edit the Web.config with the following changes:

<?xml version="1.0" encoding="UTF-8"?>
			  <clientCache cacheControlMode="UseMaxAge" cacheControlMaxAge="1.00:00:00" />
                <rule name="LetsEncrypt" enabled="true" stopProcessing="true">
                    <match url="\.well-known/acme-challenge/*" />
                    <conditions logicalGrouping="MatchAll" trackAllCaptures="false" />
                    <action type="None" />
                <rule name="Https redirect" enabled="true" stopProcessing="true">
                    <match url="(.*)" />
                    <action type="Redirect" url="https://{HTTP_HOST}/{R:1}" redirectType="Permanent" />
                        <add input="{HTTP_HOST}" matchType="Pattern" pattern="^domain.tld$" ignoreCase="true" negate="false" />
                        <add input="{HTTPS}" pattern="^OFF$" />
                <rule name="ReverseProxyInboundRule1" enabled="true" stopProcessing="true">
                    <match url="(.*)" />
                    <conditions logicalGrouping="MatchAll" trackAllCaptures="false">
                        <add input="{HTTP_HOST}" matchType="Pattern" pattern="^domain.tld$" ignoreCase="true" negate="false" />
                    <action type="Rewrite" url="{R:1}" />

Explanation of the three rules

  • LetsEncrypt
    • This is to allow renewal of the certificate. This is set before the redirect of requests to HTTPS.
  • Https redirect
    • Force https requests of all request that does not math the above rule.
  • ReverseProxyInboundRule1
    • Rewrite the inbound request to the http webserver which in my environment is hosted on a different server. But might also just be localhost.

Step 3

Start Certify the Web where you will be asked to create a new primary contact.

Fill in the form and click "Regsiter Contact". This information is used when requesting certficates from Let's Encrypt.

Click the "New Certificate".


Select the IIS site you want to create a certicate for.

It will then show the hostname on that site. You can then selected what sites you want to create a Certicate for. Remember this hostname needs to be accessible from the outsite. Hence my name here: 'racing.localtest.me' will work not.

You can also select the primary domain for the certicate if there is more than one.

On the Advanced tab there is diffent options, which I havent used yet. But the web hook option would nice if you want to noticed either when a Success or Error eccours when requesting a new certificate.

If everything goes well you will now have a site running https with a valid and FREE certificate.

Windows Server 2008 R2 takes forever to start up–60 minutes or so

So a few weeks ago I disabled Ipv6 from the Local Area Connection on my Windows Server 2008 R2. I was changing the gateway and I thought, I’m not going to use it, so I could just as well disable it.

The server is running:

  • Active Directory
  • Exchange 2010
  • TFS 2010
  • DNS
  • IIS


Today I decided to install some windows updates. There were about 16 of them, and one for Microsoft Exchange 2010 SP1 Rollup2 ( I think the name was ).

It took forever to install … but finally after 1 hour is was done and I reboot the machine. It took forever to boot up ( Applying computer settings ) … again 1 hour … login took about ½ hour.

I could see it answered on the IP address … so it was not frozen or anything like that. Did a little googling and found a post mentioning NOT to disable ipv6 because some part of Windows Server 2008 R2 can’t function with out it, unless you also do some register editing. Ohh My Freaking God.

Microsoft … I’m sending Sons of Anarchy over to do some payback. Smile

Adding users to a TFS Project from the server

I have a few servers running, but they are all external to me, as they are placed in a data center, so my own computer aren't joined to the domain.

  • SS-Exchange: DC, Exchange

This haven't been a problem before at all. So the other day one of my friends asked if I could host a TFS Project for him on my server. No problem, so I created the user in the DC, created the project and the last thing to do was just to add him to the project so he would have access to it, and then the problems started. As my own computer was not part of the domain, I could only add local users, from my own computer. I hadn't been a problem before as my user was “TFS Administrator” so I had access to all projects.

So I started binging/goggling the net, but to no avail. I was puling my hair out … ARGHH.

Then I decided to ask a question on serverfault with the title TFS 2010 - Adding users to a Team Project. Is was slow with comments in the start, but there come a few, buy they did not really help me much.

So I thought it was not possible at all, and a BIG #FAIL by Microsoft.

Then a Anthony come with an interesting comment you can read here.

So I started looking around again as I could not make his suggestion work, probably because I did something wrong since it worked for him. But when jumping around in the “Team Foundation Server Administration Console” I found what I had been looking for all the time. Not the first place to look … but here are the details needed.

Follow the numbers on the above picture.

Again, click the number in the order.

Follow the numbers as before.

The rest for here should be like a walk in the part. God darn this is a well hidden feature that its done from the “Valid Users” properties on the group. But is was here.