certificate - Trust a self signed cert from IIS

Question

I have an externally hosted iis webserver where i run my website. I would like to add a self signed certificate to this website and trust it on my local client, to remove "Insecure Connection" from the browser.

What i have done so far is the following

1. Created a self signed certificate in IIS: Server Certificates -> Create self signed Certificate. The cert is issued to the servername e.g "ABCD01"
2. Created a website with a https binding using the self signed certificate.
3. Exported the self signed certificate from IIS using: Server Certificates -> Export. This resulted in an .pfx file
4. Imported the .pfx cert file on the local client: manage computer certificates -> Trusted Root certification authorities -> import
5. Added the hostname (ABCD01) and ip of the host to the hosts file: C:WindowsSystem32driversetchosts

When i try to open the website in firefox (using https://ABCD01), i still get the "Your connection is not secure". What am i missing?

Answer 1

There are multiple issues:

1. IIS certificate generator creates self-signed certificates with SHA1 signature algorithm which is obsolete in modern browsers. You have to use different tools to create test certificates. For example, use PowerShell New-SelfSignedCertificate cmdlet where you can specify signature algorithm. Look at this post to get an example: https://stackoverflow.com/a/45284368/3997611

New-SelfSignedCertificate `
    -DnsName "ABCD01" `
    -CertStoreLocation "cert:LocalMachineMy" `
    -FriendlyName "test dev cert" `
    -TextExtension "2.5.29.37={text}1.3.6.1.5.5.7.3.1" `
    -KeyUsage DigitalSignature,KeyEncipherment,DataEncipherment `
    -Provider "Microsoft RSA SChannel Cryptographic Provider" `
    -HashAlgorithm "SHA256"

2. IIS certificate generator cannot build certificate with SAN (Subject Alternative Names) certificate extension which is required in Google Chrome. You have to use different tools to create test certificates. Look at the example above for reference.

3. Google Chrome uses built-in Windows Certificate store to establish a trust, while FireFox uses its own certificate store. Therefore, after adding the certificate to Windows certificate store, you have to import your test certificate to FireFox manually.