Can I use a self-signed X.509 certificate on a different HTTPS server? - iis

I have created my SSL certificate using Selssl7.exe on server1 but used Cn as Server2 and hosted the certificate on server2. I started to get a certificate error when browsing from linux firefox saying:
This certificate is invalid, the certificate is not trusted and is self signed, the certificate is only valid for server1
But when I browse the URL from Windows IE I just get the regular error saying that it's not trusted and I can easily add it to exceptions.
Can we use self-signed certificates generated on server1 on a different servers?

You can and you may but you are pretty much undermining each and every aspect of authenticity by doing so.
A self-signed certificate is generally a problem because other users will not know this certificate in advance. So their browser dutifully issues a warning. That's why you have to pay for TLS certificates that will be recognized - they are issued by CAs whose certificates are contained in the default trust store of your browser. CAs had to pay to "be part of the club", but otherwise, anyone can create certificates. It's just the matter of being recognized by default settings.
But you open another hole by reusing a certificate that was issued for a dedicated server on a different server. TLS certificates' subject distinguished names must match the host name of the server they are deployed on. This is mandated by the TLS spec because this is the only effective measure to prevent man-in-the-middle attacks when using TLS. After you open a TLS connection to a server, your code will check whether the host name that you are connected to matches the subject DN of the server's certificate that was sent. Only if it does you can be sure to be talking to the right server.
So, in conclusion, if you reuse a server certificate on a different host, then you are severely impacting the security of TLS. It's still possible, sure, but if you cripple security to this extent, then you are probably better off using plain HTTP in the first place.

Related

PKI: web server certificate

I'm learning the process of authentication in PKi environement.
Imagine I have two web servers (example IIS) that are configured with same TLS certificate to bind websites.
Now, if I remove and add a new certificate on one of two servers. It's still have the same common name but generated with a different private key.
I wonder if having two certificate with the same common name (subject) with two different private keys will be a problem?
What information is used by the client to choose a specific public key to encrypt information?
I hope that my question is clear. Let me know if you need more information.
Many thanks for your help.
No matter how many certificates you installed to Windows certificate stores, IIS only uses the mappings in Windows HTTP API to determine the actual server certificate to use for a specific site,
https://docs.jexusmanager.com/tutorials/https-binding.html#background
If you are familiar with SSL/TLS handshake process, you can easily see in that way the browser always knows which public key to use.
Will it be a problem? The answer is maybe.
Assuming a modern browser, then the PKI works broadly like this:
the browser first uses DNS to resolve the FQDN into an address;
then the browser sends a TLS client hello to it, which contains an
SNI matching the FQDN;
the server receives the TLS client hello, checks whether the FQDN matches ones it owns, then responds with a TLS server hello containing the X.509 certificate;
the browser receives the TLS server hello, then checks that the certificate is valid;
that the SubjectAltName (SAN) field contains the FQDN (SAN has replaced
CN); and
that the certificate is signed by a CA that it trusts.
At this point the browser doesn't actually care whether you have multiple servers with multiple different certificates (which can be normal during a patch where they are being revoked and replaced).
The maybe comes afterwards, because there are a collection of HTTP extensions that can cause the browser to reject the certificate if it does not comply with what it is expecting, such as Expect-CT and HSTS.

This Connection is Untrusted issue

I get the following error message.
You have asked Firefox to connect securely to www.gstatic.com, but we can't confirm that your connection is secure.
Normally, when you try to connect securely, sites will present trusted identification to prove that you are going to the right place. However, this site's identity can't be verified.
What Should I Do?
If you usually connect to this site without problems, this error could mean that someone is trying to impersonate the site, and you shouldn't continue.
This site uses HTTP Strict Transport Security (HSTS) to specify that Firefox only connect to it securely. As a result, it is not possible to add an exception for this certificate.
www.gstatic.com uses an invalid security certificate.
The certificate is not trusted because the issuer certificate is unknown.
The server might not be sending the appropriate intermediate certificates.
An additional root certificate may need to be imported.
(Error code: sec_error_unknown_issuer)
Can someone please help me to solve this issue :'(
You're receiving this error message because the certificate for the site isn't valid. In order to communicate using SSL with a site, the site must provide a valid certificate. There are a number of things necessary for a valid certificate, but one factor is the certificate must be issued by a trusted certificate authority, or CA. Your browser is preconfigured with a set of trusted CAs, but for this particular site, the issuer is not part of that set of trusted authorities.
Furthermore, since the site is using HSTS (HTTP Strict Transport Security), an exception cannot be made for this certificate.
You'll need to view the certificate and see who issued the certificate (the CA) and whether that is a real CA. The certificate may be self-signed, which means the site issued their own certificate without a trusted CA. If you wish to continue, you'll have to install the issuer's certificate as a trusted CA in your browser. However, do not install the issuer's certificate if you cannot verify their identity as a trusted CA.
This article on your particular error may provide guidance on why you're seeing this message. Here's a general description on how SSL works and what roles certificates and CAs play.
With regard to the first solution, if you end up having to install a CA cert into your Firefox browser, click Edit Trust and check the "This certificate can identify websites" checkbox. If that checkbox is not checked, then Firefox will still not trust websites who issue certificates signed by that CA.

Are certificates useful for intranet SSL?

I've been tasked with development of an intranet interface for command line software, and now I'm researching security options. Our command line application is finished, but I haven't started writing the web interface. I don't know exactly what the security requirements are for potential customers, although I believe ssh is generally acceptable for the command line interface. With this in mind, I'm asking for help developing a menu of choices with their associated pros/cons. Some day, we may consider releasing our web interface to the internet, so I'm willing to consider more security than currently necessary if it's easy and/or free.
I've been doing a lot of reading, and my tentative conclusion is that SSL security with no certificate is the best approach, not because less security is unacceptable, but because SSL is the standard and because it doesn't appear to be difficult to set up. I, a security non-expert, wouldn't need to explain why less security is acceptable to security non-experts. I could upgrade my application to use a certificate in the future if necessary.
Here's a list of SSL related security choices, sorted by my perception of security level with my comments. What level of protection do I need?
No SSL. This might be acceptable if our customers aren't worried about their employees seeing/changing each others' data. Their employees might want to share results with each other anyway, and I could use IP based access control and/or passwords for security.
Do SSL with no certificate. This encrypts the communication, which at least protects the data from being read by unauthorized employees. Using a password, this is the same level of security as ssh on the command line, right? I don't need to worry about man-in-the-middle attacks in an intranet, right? A con for this approach would be if there were loads of browser warning messages.
Do SSL with a self-signed certificate. What does this give me that no certificate gives me? If the DNS can be changed inappropriately, then the customer then my application is the least of their concerns. Worded another way, if the DNS can change, then I think ssh would be vulnerable too.
Do SSL with a local Certificate Authority. OpenSSL lets me make my own Certificate Authority. What does this give me that a self-signed certificate does not? I'm assuming that on a LAN, it's less important for the server to be verified.
Do SSL with an external Certificate Authority. Is there ever a reason to go this route for an intranet? I found some "intranet certificates" for sale online -- but it's not clear what they're offering I can't do myself.
For reference, this page might be useful for comparing certificates:
http://httpd.apache.org/docs/trunk/ssl/ssl_faq.html#aboutcerts
[update]
Here's an article discussing the risks and rules of obtaining an internal certificate from a public CA.
Yes, certificates are still useful for Intranet SSL.
There's an important difference between SSH and SSL-without-a-certificate: when you first connect to a server with SSH, your SSH stores the server's fingerprint. If you then try to connect to what the SSH client believes to be the same machine but gets back a different fingerprint, it alerts you that there might be someone intercepting your communications.
SSL-without-a-certificate, on the other hand, does not store the server's fingerprint. Your communications will still be encrypted, but if someone somehow hijacks the DNS server as you mentioned, or, as Rushyo notes, does ARP poisoning or something similar, they would be able to perform a man-in-the-middle attack. SSH, as previously mentioned, would (supposing you had connected to the correct server some time in the past) notice that the fingerprint had changed and alert you.
A self-signed certificate would be comparable in security to SSH. A man in the middle could generate their own self-signed certificate, but as long as your applications are configured to only accept that self-signed certificate, you should get an alert similar to that that SSH will give you.
A local certificate authority gives you security similar to self-signed certificates, but may be more scalable. Should you have multiple servers, each can have their own certificate, but a client only needs the top-level one to trust all of them. If a server is compromised, you can revoke its certificate rather than having to change every server's certificate.
I don't believe an external certificate authority has any advantages, other than possibly less configuration if your machines already have the certificate authority trusted.
Lastly, I don't know enough about two-factor authentication to evaluate it, but for most applications, SSL should be sufficient.
Disclaimer: I am not a security expert.
Do SSL with an external Certificate Authority. Is there ever a reason to go this route for an intranet? I found some "intranet certificates" for sale online -- but it's not clear what they're offering I can't do myself.
The benefit is that you don't need to learn how to setup your own Certificate Authority if you need to manage a decent number of certificates and/or machines. Such a certificate would already be trusted by all browsers without you needing to install your own certificates into the trusted store.
However, this is actually less secure because somebody could purchase a certificate for a different intranet and use it on your network. For this reason, SSL vendors no longer offer this service. For more information, see: https://www.godaddy.com/help/phasing-out-intranet-names-and-ip-addresses-in-ssls-6935
If you only have a very small intranet, then I would recommend using a self-signed certificate, and then just add each self-signed certificate to each computer's trusted store.
However, it quickly becomes impractical to install a new certificate on every computer in your intranet whenever you want to add a new computer. At this point, you want to setup your own Certificate Authority so that you only need to install a single CA certificate in each computer's trusted store.

Issuing auto signed certificate - IIS 7.5

I issued a self signed certificate on IIS 7.5, and it is working correctly if i access my website through my computer.
However, if i access the website from another computer, i get an warning saying the certificate was issued to another address.
Is this because the certificate was issued to localhost instead of the actual IP?
Or this doesn't make any sense?
Regards,
The error message you are getting is normal, assuming you do not have anything in your certificate aside from 'localhost' to identify the owner.
Your browser is performing a name check, and looking to validate the certificate that is presented with the URL you typed in. Typically, the common name of a certificate matches the hostname/DNS name of the machine. Alternatively, there can be information inside of the Subject Alt Name (SAN) extension of your certificate. There, you could specify multiple DNS names or IPAddress fields that identify your server in addition to the CN.
If you are simply performing internal testing, I would not be terribly worried about the warning you are receiving. Just keep all of this in mind when you move to production. Also, having your CA being self-signed, you may also receive trust warnings, unless you manually import your self-signed CA certificate into the trust store of the browser you are using.
Maybe this helps you: Self signed certificates on IIS 7. At the end of the article, in the section named "Adding the Certificate to Trusted Root Certificate Authorities", an alternative solution is shown, but it implies importing the certificate in the client machine, so that could be a huge disadvantage. However, it is a solution if you can't register the certificate on a Certificate Authority, an you have access to the client machine.

How does SSL actually work?

Whenever I see it being talked about, it sounds like one simply 'turns on' SSL and then all requests/responses to/from an online server are magically secure.
Is that right? Is SSL just about code - can I write two apps and make them communicate via SSL, or do you have to somehow register/certificate them externally?
Secure web pages are requested on port 443 instead of the normal port 80. The SSL protocol (plenty complicated in and of itself) is responsible for securing communication, and using the certificate information on both the SERVER and the BROWSER to authenticate the server as being who they say they are.
Generating an SSL certificate is easy. Generating one that is based on the information embedded in 99% of web browsers costs money. But the technical aspects are not different.
You see, there are organizations (Verisign, Globalsign, etc...) that have had their certificate authority information INCLUDED with browsers for many years. That way, when you visit a site that has a certificate that they produced (signed), your browser says:
"well, if Verisign trusts XYZ.com, and I trust Verisign, then I trust XYZ.com"
The process is easy:
Go to a competent SSL vendor, such as GlobalSign. Create a KEY and Certificate Request on the webserver. Use them (and your credit card) to buy a certificate. Install it on the server. Point the web-browser to HTTPS (port 443). The rest is done for you.
SSL is a protocol for encrypted communications over a TCP connection (or some other reliable scheme). The encryption uses public key encryption using X.509 certificates. SSL handles both privacy and trust. These are related: if you don't trust the server, you don't believe that the server hasn't handed out its private key to everyone in North America.
Thus, the client has to trust the server's certificate. For public sites, this is arranged via a hierarchy of certificate authorities, with the root authorities trusted, automatically, by browsers and things like the JRE's socket implementation.
Anyone can generate a self-signed certificate for a server, but then the client has to be manually configured to trust it.
SSL is not, in itself, a magic bullet that makes everything secure. Security has no such things.
SSL is, however, an already-designed, ready-to-use system for solving a common problem: secure stream communication over a network connection.
There are two things you need to do to secure your application with SSL:
Modify the application's code to use SSL.
Determine the certificate trust model (and deploy and configure the application respectively).
Other answers and documentation provide better answers to how to do each of these things than I could provide.
I'll throw caution to the wind and attempt to condense an enormous subject.
SSL attempts to solve two problems:
1) Authentication and hence trust i.e can the client trust the server and vice versa
2) Communication without eavesdropping
1) Is handled by means of an intermediary i.e a trusted 3rd party - these are called 'Root Certificate Authorities' ( or Root CAs ) examples include Verisign, RSA etc
If a company wants to authenticate users and more importantly if a user wants to authenticate the company's website it's connecting to i.e your bank then the Root CA issues the company a certificate which effectively says 'I the trusted Root CA verify that I trust that Company X are who they say they are and am issuing a certificate accordingly'. So you get a chain of trust i.e I trust the certificate from ACME Co because Root CA Verisign created and issued it.
2) Once the two parties have authenticated then the certificate ( typically X590 ) is used to form a secure connection using public/private key encryption.
Hopelessly simple and incomplete but hope that gives a rough idea
Yes and no. You should self-sign a certificate and test the site with SSL internally before deploying it with SSL, first of all. To make the public site secure under SSL, you will need to purchase a certificate from one of any number of certificate providers. Then you will have a certificate signed by a trusted third party, tied to your domain name, so that users' browsers won't complain that the certificate is invalid, etc. Turning SSL on is pretty much just flipping a switch, otherwise.
For the most part you need to buy and register a certificate externally.
You need to have your server certificate signed by a Certificate Authority (CA), for which they will charge you. The client needs to trust that CA and have a copy of the relevant CA public key. The client can then check that you are who you claim to be (including domain name (from DNS) and display name for https).
This is a good tutorial on how to create self signed certificates for Apache.
If you want to know how SSL works on either the Server or the Client, then I suggest Googling it. As you suspected, it is a ridiculesly complex procedure, with lots of communication between the client and server, a lot of very peculiar math, and tons of processing. There is also a lot of theory involved, several protocols and many different algorithms and encryption standards. It's quite incredible how changing http:// to https:// is so simple to the user, but results in so much work for both sides, and is so secure. To really understand it you need to take a security course (multiple courses to fully understand it), as the entire history of encryption goes into making your login to Gmail secure.
Turning on TLS (colloquially "SSL") does not make your site magically secure. You may still be vulnerable to application-level vulnerabilities like stack overflows, SQL injection, XSS, and CSRF.
As other answers have explained, TLS only protects against a man in the middle. Traffic between a client and a properly-configured TLS server cannot be intercepted or modified, and the client can reliably confirm the identity of the server by validating the X.509 certificate. This prevents an attacker from impersonating your TLS server.
SSL actually does two things:
Encrypts the communication so that an observer seeing the data stream will not be able to read the conversation.
Guarantees that you are talking to who you think you are talking to.
It is only for #2 that you need to get official certificates. If you only care to encrypt the communication without setting up a trust relationship, you can use self-signed certificates or you can use an algorithm that does not require certificates (i.e. Diffie-Hellman).

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