How can a client-side user get an SSL key? - ssl

I have an IIS 7.5 web server with an SSL certificate setup as follows:
Select "Default Web Site" -> Bindings:
Type: https (all other types removed)
IP address: All Unassigned
Port: 443
SSL certificate: mycert.pfx
I have a C# client application that accesses the URL for the site above. If the user just tries to connect, the connection fails because they do not have the mycert.pfx certificate file installed.
When the clients were on Windows 7, we just told them to open the URL in Internet Explorer. This required them to "Proceed Anyway - Not Recommended". The URL bar would turn red, and the user could follow steps to download/install the certificate with Internet Explorer. After that, the application always worked.
In Windows 10, the default Internet Explorer does not offer a "Proceed Anyway - Not Recommended" link. If I keychain the mycert.pfx file to their machine and install, the client application connects to the server and everything works.
Finally, here's my question: How do people handle certificate file deployments in a large commercial environment? The .pfx certificate has to be renewed every year, so just adding it to the application installer is only a short term fix. Is there a typical way to install/update .pfx files for clients?

Randy
Your pfx files should never be shared with the client. the public key chain is shared with the client. PFX file contains the private key of the certificate which you have procured from a CA which must never be shared.
The client application will verify the certificate chain received from the server with the public root and intermediates which are pre installed in its certificate store.

Related

IIS SSL Certificate No longer visible from internet

Pulling my hair out here. Yesterday I set up an SSL Certificate in IIS10. This is the process I followed:
In IIS, under Server Certificates complete Create Certificate Request (generated server.csr & server.key)
Go to sslforfree.com and start "create certificate" process.
Enter Static IP in Domain box
In Validity, choose paste Existing CSR (paste in contents of server.csr)
Select free 90 day certificate
Choose HTTP file upload and add auth file to virtual share in IIS.
Verified OK.
Download certificate
Back in IIS, select "Complete Certificate Request"
Browse to and select "certificate.crt" file.
Give it a friendly name etc, and save.
Browse to website under sites in IIS, and select Bindings. Choose the IP of the server, the incoming Port, and the newly imported SSL certificate.
Back in sslforfree, check the installation.
Everything all good
So everything was working beautifully, could see the certificate in the browser etc, job done.
Now come to today, and the server is actively refusing requests. Go back to check the installation of my SSL on sslforfree, and it's no longer found. Tried removing and re-adding, but nothing I do seems to get the SSL to be visible.
It's not that the certificate is refused, the browser doesn't even think it's there. Why would IIS suddenly stop sharing the certificate? I am totally stumped.
EDIT
As per the advice below, I set up a DNS name with CloudFlare and pointed it at my server.
I Set up the bindings in IIS to link to the new hostname and removed the old certificate (one for port 443 and this one for port 4443 which the API runs on):
Ports 80, 443 and 4443 are all port-forwarded on the router to my server:
I then downloaded Win-ACME and successfully created the Let's Encrypt certificate, and the renewal task created in Task Scheduler.
SSL Cert now shows in Bindings:
SSL Certificate appears to be all good:
...but when I go to the site, using the new domain name. Same problem... no certificate:
So I'm not sure what the problem is here...
This issue may happens when the imported cert does not have a private key associated. solution would be to import the .CER file to your system(from where certificate is requested) personel store and export it with private key. Then copy the .pfx file to required server and import it from server certificate option under IIS.
And you can refer to this link: The Whole Story of "Server Certificate Disappears in IIS 7/7.5/8/8.5/10.0 After Installing It! Why!".
Thanks to Lex Li, I was able to dig around with Jexus Manager, and IIS Crypto to work out what was wrong.
Seems having TLS 1.2 an TLS 1.3 enabled on my machine at the same time was causing issues. Discovered this using Postman and disabling certain TLS Protocols, eventually getting it to work.
For those of you who may experience similar issues, using this application and setting it to "Best Practices" after disabling TLS 1.3 in my Registry, I finally have it working, with a certificate.

IIS SSL Certificate for Intranet website (Not Trusted)

I have created a self-signed certificate on IIS and added it to Trusted Root Certificates using mmc.exe and when I launch my intranet using https://ipaddress shows secure. But when I go LAN and browse for the https://ipaddress shows me not trusted. I also used on IE, which I installed the certificate but still showing not trusted. Am I missing something, please help.
Self signed certificates are not trusted by browsers as the issuer (yourself) is not a trusted Certificate Authority. However, you can trust the self signed certificate if you want by adding the particular certificate to Trusted Root Certificate store. For IE, import the certificate to the Trusted Root Certificate Authorities folder in the client machine. Note that this has to be done on all client browsers/machines to trust your certificate.
Also, there could be other reasons for not trusting the certificate, please read the error description clearly.
If you use subdomain, i.e. subdomain.domain.com, the domain administrator (IT) should provide you with a wildcard certificate.
The domain administrator generates and assign the certificate to your subdomain server, also should allow port 80 and 443 firewall rules so that users can visit the site in the intranet.
The above answered methods can be used to generate the certificate, preferably sha256 certificate. Once the certificate is provided to you, install it on your server to “Personal”, “Trusted Root Certification Authorities” and “Web Hosting”. Open the certificate to validate it installed successfully, and you can use the thumbprint to sign files, such as rdp files. To do this, on your keyboard, START + R to open the run command and enter “certlm.msc” and once the window opens, navigate to “Trusted Root Certification Authorities” and there should be the certificate that was just being imported, i.e. *.domain.com, double click to open the certificate and click on Details tab. Drag the scroll bar until the Thumbprint is visible and then click on it to revel the code. Create an rdp file to your subdomain and save it to your desired location, such as desktop. Open CMD terminal and CD to the location and enter “rdpsign /sha256 thumbprint ‘./sumdomain.domain.com.rdp’”. Done, now when you open the connection, the compute should be trusted to connect to RDP, this process is not necessary, but it is nice to see the publisher is recognized.
The benefit of having the *.domain.com certificate generated for your organisation is that users should have this certificate already installed on their PCs and when they visit your website, users would automatically see the HTTPS secure padlock for SSL certificate. The certificate would usually be generated to allow all subdomains, i.e. *.domain.com.
IIS, When setting up the HTTPS binding on your IIS settings, check the "Require Server Name Indication" and continue to browse for the certificate and select and save the settings. Also turn off Directory Browsing while you’re there. Go to SSL Settings and check on Require SSL and hit Apply and go back. To control the flow of HTTP to HTTPS when users visit your site, you can use “URL Rewrite”, install it from Microsoft and you can do the configuration, please check on https://www.ssl.com/how-to/redirect-http-to-https-with-windows-iis-10/ for the appropriate settings. Even though, this answer is out of the scope for the question, it may be helpful for anyone who look forward to configuring their intranet site. Next to checkout is the security for who accesses your site, check on AppPoolIdentity, more help on IIS7 Permissions Overview - ApplicationPoolIdentity.

Biztalk send port cannot find certificate

Good afternoon,
I'm getting the following error trying to use a BizTalk send port to talk to a web service:
"System.InvalidOperationException: Cannot find the X.509 certificate using the following search criteria: StoreName 'My', StoreLocation 'CurrentUser', FindType 'FindByThumbprint'
The send port is configured as type 'WCF-WShttp', 'Transport' security mode, 'Certificate' credential type.
I have a self signed certificate that has the same thumbprint value as shown in the bizTalk configuration dialog. I've checked the file shows the correct thumbprint and it is not expired.
I've tried installing it in the all the following stores:
"Current User": Personal, Trusted Publishers, Trusted People, Trusted CA's
"Local Computer": Personal, Trusted Publishers, Trusted People, Trusted CA's.
When I go to the wcf send port configuration in the BizTalk management console it allows me to browse available certs. Our cert appears and lets me select it.
I made sure the service account for biztalk is added to the cert permissions.
Any suggestions?
Thanks!
The client certificate needs to be installed in BizTalk host user account certificate "Personal Store", also make sure any root certificate (if any) is in trusted store and then set it on adapter configuration.
Following these procedures should work. https://msdn.microsoft.com/en-us/library/gg634534(v=bts.70).aspx. Probably the most important thing to note is that you must be logged on to the server with the actual account that is running the adapter handler's host instance service. And for a self-signed certificate I think you just need to add it to the Trusted Root CAs for that account too.
Did you copy the thumbprint directly from the mmc to your BizTalk Send Port.
First try to copy it to notepad++ and check if you see any special characters.
If that's the case remove the special characters and then copy that thumbprint to your BizTalk Send Port.

Exporting the SSL certificate with the private Key on windows

I am in a process of generating an SSL cert for a domain name.
What I have done:
Went to the IIS management > Server Certificates and clicked on Create Request. This generated a *.com file with a hash inside it that I submitted to the GoDaddy.
From GoDaddy I got back a zip with two files: *.crt and *.p7b
I exported the certificate to a *.cer file and uploaded it to Azure, but when I try to deploy the cloud project I get an error:
Certificate with thumbprint associated with HTTPS input endpoint
does not contain private key
After reading similar issues on the Internet, I understand that my *.cer file doesnt contain the private key.
My problem is that no matter how I try to export it to a *.PFX, the PFX option is always disabled in the cert export wizard.
Also not sure if it is related, but when I Click on Complete Certificate Request in IIS and select the cert that I got from GoDaddy. I get an error:
Cannot find the certificate request that is associated with this
certificate file. A certificate request must be completed on the
computer where the request was created.
You will not have the option of exporting from IIS or exporting to PFX from Certificate Manager if you do not do the IIS "Create Certificate Request" and "Complete Certificate Request" from the same machine.
That was my problem. I did these two steps from two different machines.
I had to create a new request (in IIS), go to GoDaddy, rekey my certificate, download the new certificate, and then complete the request (in IIS).
This turned out to be something completely idiotic, as usual messed up by Microsoft.
The process of creating a cert for a domain is that you need to use [Create Certificate Request] in IIS.
Then send the created hash to the Authority and use the [Complete Certificate Request] in IIS where you provide the cert given to you by the Authority. This will install the cert into your local IIS
After the cert is installed you need to right click on it and do an export to a *.PFX file. The PFX file now can be uploaded to Azure or any other hosting...
The processes could have been very simple, if Microsoft didn't make sure to screw it up.
The thing is that when you click on [Complete Certificate Request], the file open dialog has a file type of *.CER, but this is wrong because you need to provide *.CRT!!! The solution is to change the file type select to All Files *.* and chose the *.CRT file provided by the Authority.

How to generate an SSL client certificate from a disconnected network?

I have a unique situation where I need to implement client certificate authentication over HTTPS between IE browser and IIS 6. The browser and IIS are separated by a firewall that only allows the browser to connect to IIS on the SSL port.
We have an internal certificate server on the same network as IIS. I've generated an SSL server cert for IIS and that is installed. I configured IIS to only allow SSL, require client certificates.
The limitation here is the browser machine is on a disconnected network, so I can't go to the CA's http://caserver/CertSrv URL and request a client cert like you normally would.
I figured if there were a way that I could generate a CSR against the Root CA's public key, I can copy it to the CA server to generate the client cert. But, there appears to be no provision in IE or the Certificates MMC to do this. The Certificates MMC seems to require a direct connection to the CA.
Has anyone solved this before?
FYI, All servers referenced run Windows Server 2003.
Update: Thanks to Jonas Oberschweiber and Mark Sutton for pointing out the CertReq.exe command line tool. Using this, I've generated a CSR, and consequently a client certificate that installs successfully. However, IE is apparently not sending this client cert when accessing the IIS server in question; it still generates a 403.7 "Forbidden: SSL client certificate is required." I suspect that the reason is that the Subject field of the client cert does not match the user id of the account running IE, thus perhaps not sending a mismatching client cert. The Subject matches that of the user I used to submit the CSR and generate the client cert on the other end of the firewall.
Does the Subject field matter? Is there something else I need to do to enable IE to send this cert?
Use the certreq command on your client as follows
certreq -new -f filein c:\certrequest.req
Here is and example of the filein
[Version]
Signature="$Windows NT$"
[NewRequest]
Subject="CN=dc1.extranet.frbrikam.com"
EncipherOnly = False
Exportable = False
KeyLength = 1024
KeySpec = 1
KeyUsage = 0xA0
MachineKeySet = True
ProviderName = "Microsoft RSA SChannel Cryptographic Provider"
ProviderType = 12
RequestType = CMC
[RequestAttributes]
CertificateTemplate=TLSServer
Replace the CertificateTemplate with the name of your certificate template
Once you have your request file you need to take it to the certificate authority on a usb stick and use the web enrolment interface as usual to process the request file.
Take the output certificate back to the client open it and click install.
You sound like you have already tried a couple of things so my guess is that you are already aware of these, but I'm going to post them anyway, just in case: Certificate Command Line Tools. I am not sure, however, if they do what you want.
Go the http://caserver/CertSrv site that you mentioned using a 3rd computer that can see the CA server. Select the 3rd option, download a CA cert, cert chai, or CRL. On the next page select 'Download CA Certificate Chain', which will download the p7b file. Using a flash drive (or email, etc) transfer this to the other computer which will allow you to import it into the trusted root servers in IE.
http://technet.microsoft.com/en-us/library/cc787796.aspx
Suggestiong for the update, just in case - what is the trusted cert list of in the server?
Subject DN being the same as Windows username has never been a problem for me - although I don't use IIS much. However, somewhere in IIS there is sure to be a trusted certificate list. This error sounds to me like the server's trusted certs list does not include the CA or Root CA that issued the client certificate.
This is particularly true if you never get a certificate selection popup window in IE when you hit the IIS server - even though you have a certificate configured in your IE cert store. That means that the client hit the server, the server gave a list of trusted certs and the client didn't have a cert that fit the list. So the SSL session went to the Forbidden error state.
If the certificate selection window popped up, and you selected and sent the cert, there may be other configuration problems on the server side..