Certificate Authentication in Key Vault - security

I have some secrets that I would like to keep in Azure Key Vault. I know I can use a client id and certificate to authenticate with Key Vault instead of using a client and and secret following these steps:
Get or Create a Certificate
Associate the Certificate with an Azure AD application
Add code to your application to use the Certificate
Most examples use either makecert or New-SelfSignedCertificate to create the certificate. Is a self signed certificate problematic in this case for a production application? This is only for an application to authenticate with Azure Key Vault and it's not something a client will ever see in their browser.
If a self signed cert is still frowned upon in this case then is purchasing a cert from a trusted authority the same process as purchasing an SSL/TLS certificate? Is it even the same type of certificate?

There is (with some caveats) nothing inherently wrong with using a self-signed certificate. There is no difference from a pure crypto perspective between a purchased and a self-signed certificate. The sole difference is that a purchased certificate has been signed by one or more certificate authorities (CAs) who distribute their public keys with most browsers/operating systems/etc. This means that a user can have a much higher confidence that a purchased certificate is legitimate, while they must take a leap of faith to accept a self-signed certificate.
In your case, however, you seem to be able to control the client application, and actual users should never see this certificate. Therefore, you can use a self-signed certificate without worry, so long as you take precautions to prevent man-in-the-middle attacks (i.e. someone generating their own self-signed certificate and pretending to be you.). One of the most effective ways to do this is via certificate pinning. In essence, you ship the public key for your certificate with you client application, and your client application will only accept certificates that provide that public key. This makes it much more difficult for a malicious actor (who has not stolen your certificate) to preform a man-in-the-middle attack.
TL;DR: So long as you take steps to prevent man-in-the-middle attacks, and you keep your certificate secure, there is nothing wrong with using a self-signed and self-generated certificate to secure non-user-facing connections.

Related

Mutual authentication - setup, flow, verification

I am implementing mutual authentication between a single client hosted app (CLIENT) and my spring boot 2 application (SERVER). I understand the steps to be as follows:
The server generates a keystore and truststore. The keystore being used for storing the server's certificates and private key. The truststore used for storing other credentials (certificates from certificate authority (CA) or trusted client certificates).
A CSR is raised for the server which is then passed to a CA. The CA generates a signed certificate from the CSR. This is the installed in the server keystore.
The client (which has it's own keystore and truststore) provides their public key to the server. This is then installed in the server truststore.
When a https request is made from client to server:
The client makes a request to access a protected resource.
Server responds with their public certificate.
Client verifies that certificate (looks in truststore and checks if it signed by a trusted CA).
Client presents their public certificate to server.
Server then verifies certificate against their truststore.
Assuming verification success client is granted access to the protected resource.
So I have a few things which I'm a bit confused about...
Are the steps outlined above broadly correct?
How does the server verify the client certificate? (I think it looks at the truststore for that certificate but not sure what actually happens after that).
I've seen examples of the CA certificate being installed in the server truststore instead of the actual client's public certificate ~ is there a use case when this should or should not be done? For my use case I have been provided with a signed certificate from the client (third party). The CA who signed that is different from the CA who signed the server certificate.
Does this process actually authenticate the client i.e. this client can now have access to the servers protected resources but another client who might present a different certificate will not have access? (like a more secure method of providing a username and password)
Where does common name (CN) checking come into all of this? I note in Spring Boot X.509 you can derive a username from the CN and then use this to lookup the appropriate user details from the user details service.
If the client certificate gets compromised for whatever reasons is this managed by just removing it from the server's truststore?
Is there an advantage, in my scenario of using a trusted CA e.g. verisign to produce a client certificate over a self-signed one? i.e. the certificate is passed to me directly from the trusted third party, and then installed.
In respect to your first question, yes your outlined steps are correct! Here is the general mutualSSL flow with a graphical overview: (source)
A client requests access to a protected resource.
The server presents its certificate to the client.
The client verifies the server’s certificate.
If successful, the client sends its certificate to the server.
The server verifies the client’s credentials.
If successful, the server grants access to the protected resource requested by the client.
Your second question (How does the server verify the clients certificate?):
The server verifies the clients certificate with the help of the signature. The signature is usually a hash-value, build of the complete certificate. The hash-value is signed with the private key of a corresponding CA (certificate authority). The server verifies the signature of the client certificate with the help of the CA's public certificate.
Your third question (Servers truststore containing the clients public key/certificate or the corresponding CA certificate?):
If you use for example self-signed certificates, you probably have to import the clients public key/certificate directly into the servers truststore. If your client uses an CA signed certificate, it is appropriate for you server to store the CA public key/certificate only, because it is used to verify the clients certificate.
Your fourth question (Does this process actually authenticate the client): Yes! As you can see in the answer to your second question, the certificate is verified by checking the signature. The signature is a hash over the complete certificate. A standard X.509 contains information to identify the subject. By checking the signature the subject is authenticated. A standard X.509 certificate contains amongst other things e.g. this information:
Subject name, Subject Public Key Info, Public Key Algorithm, Issuer Unique Identifier (optional), ...
Your fifth question (Where comes CN checking?): The CN (common name) verification is executed during the certificate check. The CN identifies the valid hostname for the current certificate. It is limited to one entry. As an extension the SAN (subject alternative name) was introduced. A certificate can contain more than one SAN. The CN (and the SAN) entry is part of the certificate and is verified with the help of the certificates signature check.
Your sixth question (If the client certificate gets compromised for whatever reasons is this managed by just removing it from the server's truststore?): Therefore the CAs use so called revocation lists. If you are using for example self-signed certificates it would also be okay to just remove the compromised certificate entry from the servers truststore.
Your seventh question (Is there an advantage, in my scenario of using a trusted CA e.g. verisign to produce a client certificate over a self-signed one?): There exist a few advantages of using a CA signed certificate instead of self-signed ones.
The certificate and eventually the revocation is managed by the CA
The certificate is valid to every relying party of the public CA, e.g. Verisign
Most of the public CAs offer standardized ways of creating a certificate

What does ' self signed certificate' mean?

I want to understand what self signed certificate means.
any explanation is appreciated.
Self Signed Certificates are types of SSL certificates that are generated by an independent person (such as yourself), rather than generated by a Certificate Authority.
Many organizations are tempted to use self-signed SSL Certificates instead of those issued and verified by a trusted Certificate Authority mainly because of the price difference. Unlike CA issued certificates, self-signed certificates are free of charge. What most users are not aware of is that self-signed certificates can end up costing them more in the long run.
While self-signed SSL Certificates also encrypt customers' log in and other personal account credentials, they prompt most web servers to display a security alert because the certificate was not verified by a trusted Certificate Authority. Often the alerts advise the visitor to abort browsing the page for security reasons.
In cryptography and computer security, a self-signed certificate is an identity certificate that is signed by the same entity whose identity it certifies. This term has nothing to do with the identity of the person or organization that actually performed the signing procedure.
It means that the people who are providing the certificate are the same people the certificate is being issued to, usually done this way because it is free.
It is best to have a certificate provided by a trusted Certificate Authority however, It will cost money, but is more trustworthy.

Is it dangerous that both SSL Certificate and key got exposed to public?

Before transferring our site's registered SSL certificate pair, I want to be sure of what would happen if both the SSL certificate and key file were to get stolen. Would it be dangerous if some hacker were able to exploit our certificate with their own even though theirs won't be the same domain?
Yes. If your private key is compromised you must re-key and create new certificates. Otherwise the exploiter can impersonate you for legal purposes.
However the part of your question about 'exploit our certificate with their own' is meaningless.

How to recognize fake SSL certificates?

I've read about SSL protocol and now, I know how it encrypts data. But there is something I couldn't understand. With SSL , you're sure you're sending data to and getting data from correct server. But how?
I mean if I create a fake certificate and send it for requests of special website, how do browsers ( or other programs) detect the fake certificate?
Edit: I didn't mean to create a self-signed certificate. I meant how can someone validate my certificate if I create a certificate that its issuer and subject ,etc are something to real certificate! (the only things that are not real is Public key & signature)
TL;DR summary:
Validity of a server certificate is established by:
Host name verification
Verifying the signatures of the entire certificate chain
Performing additional checks on meta data for each certificate
Checking the revocation status of each of the certificates involved
Checking whether the self-signed root certificate of the chain is among the certificates that one trusts by default
Explanation
Let's assume you want to connect to https://mail.google.com (you can try this out in your browser!).
The (real) server will respond with a certificate that is issued to mail.google.com, i.e. in the 'Subject' field of the certificate you will find the Common Name (CN) 'mail.google.com' - cf. RFC 5280 for details on the fields of certificates. The fact that the subject is linked to the site URL is very important for the security of the whole model, and it is actively checked by your TLS implementation ("host name verification"), because otherwise there would be room for Man-In-The-Middle attacks. I.e. somebody could acquire an otherwise valid certificate and impersonate mail.google.com without you taking any notice of it.
In addition to the host name verification, your TLS implementation will also check the "validity" of the certificate. The whole procedure is rather complex and does include checking the trustworthiness of the certificate, but additionally a lot of other things will be checked, more on that in a minute.
If you view Google Mail's certificate in your browser, you will notice that there are actually three certificates shown:
mail.google.com
Thawte SGC CA
Class 3 Public Primary Certification Authority (VeriSign)
The model is that there are a few (well, unfortunately not so few anymore) trusted root certificate authorities ("root CAs") that either you could choose on your own or (more likely) that come preconfigued with your software (e.g. browser) that are blindly trusted. These trusted authorities form the anchors of the entire trust model of "PKI" (Public Key Infrastructure). The basic idea is that the trusted entities may issue certificates to other authorities and grant them permission to again issue certificates (these authorities are called intermediate certificate authorities). The intermediate CAs may again recursively apply this procedure up to a certain point, the number of intermediate CAs between an actual end entity certificate and a root CA certificate is generally limited.
At one point, an intermediate CA will issue certificates to an "end entity" ("mail.google.com" in our example). Now the process of issuing a certificate actually means that the party requesting a certificate will create a public/private key pair first, and use them to authenticate a certificate request that is sent to the certificate authority. The issuing authority creates a certificate for the subordinate entity (either intermediate CA or end entity) by "signing" that certificate using its own private key using an asymmetric algorithm such as RSA and by additionally including the public key of the requesting party within the newly generated certificate. The root CA possesses a so called self-signed certificate, i.e. the root CA is the only authority that may sign their own certificate and include their own public key. The private key remains hidden at all times, of course.
The recursive nature of the certificate issuing process implies that for each end entity certificate there is a unique way of establishing a "chain" of certificates that leads up to a root certificate authority. Now when you are presented with an end entity certificate while trying to connect to a TLS-secured site, the following procedure will be applied recursively until you end up with a root CA certificate:
Find the certificate of the authority that issued the certificate to be validated (see RFC 5280 for details). If none is found: exit with error.
Take the public key of the issuing certificate and verify the signature of the to-be-validated certificate using this public key.
Check a lot of additional things such as whether the certificate has neither expired nor is it not valid yet, "policy constraints", "key usages", "extended key usages"... (again, the gory details are in the RFC).
Certificate revocation status (more on that later)
If all checks were positive, you will ultimately end up with a certificate being self-signed, i.e. where the subject is also the issuer (such as the VeriSign certificate in our example). Now the last thing you have to verify is whether this certificate is among those that you blindly trust: if it is, all is well and the connection will succeed, if it is not, the connection attempt will be rejected.
As if this were not complicated enough already, the checks described so far do not handle cases where once valid certificates suddenly become rogue, examples being cases where a certificate is stolen or private keys are compromised (think of Comodo and DigiNotar). In these cases, the normal procedure is to "revoke" those certificates gone bad, that is you want to mark them as being invalid starting from a distinct point in time (they will expire at some point anyway, but for the remainder of that period they shall already be marked as invalid). For these cases, CAs have the possibility to issue CRLs (a catalog of certificates declared as invalid) or OCSP responses (information for one or in rare cases a set of certificates) that provides clients with information whether a given certificate has been marked as invalid or not. The revocation status needs to be checked for all certificates in a chain, should one of them be marked as invalid then the end entity certificate cannot be trusted and the connection must be rejected as well.
SSL certificates are signed by a certificate authority (CA), which is someone the user already trusts (or more likely, the people who designed their operating system trusts).
The CA digitally signs the certificate using public key encryption. The basic explanation is that the CA has a "private key", and a "public key" that everyone knows. Via some math I don't understand, the CA can create a signature using its private key which can easily be verified with its public key (but the public key can't be used to create a new signature).
When you get an SSL certificate from a server, you get the server's public key, and a signature from a CA saying that it's valid (along with some other info). If you know and trust that CA, you can check the signature and determine if it's valid. You can also use a certificate revocation list to make sure it wasn't revoked.
So basically, you can recognize a bad SSL certificate because it isn't signed by a certificate authority that you trust.
Any fake certificate you create will be a self-signed certificate.
The browser will display big scary warnings when connecting to a site with a self-signed certificate which the user will promptly ignore.
In order to avoid warnings, you need a certificate signed by a certificate authority that the browser trusts, such as VeriSign.
These companies will hopefully make sure that you actually own the domain for the certificate they're signing.
Re: Edit: You can only create a non-self-signed certificate if you get it signed from a trusted CA.
They will refuse to sign a certificate for a different subject.
Process from my understanding:
server sends servers public key
server sends certificate (all information encrypted by trusted CA with their private key)
Your PC decrypts certificate with public key (built into OS from trusted CA)
Your PC hashes (with sha1 and sha256) the servers public key
Your PC compares the hashes of servers public key with certificate stored hash, if not same browser will block site
Your PC compares allowed domains from certificate and the domain, if not allowed, if not same browser will block site
Your PC compares valid date from certificate and your date, if not valid browser will block site.
To fake this you would either need to:
obtain a CA private key (extremely hard to get),
be a CA,
be part of the 5 eyes (Government intelligence agency alliance) and ask a CA for their private key
So if you see a padlock in the address bar you are almost always safe.
Certificates work because they follow a chain of trust. Certificates have a chain of one or more issuers that are trusted; this chain is the backbone of why it works at all. Browsers and nearly all SSL certificate libraries do this chain check, or at least provide the option to.
Self-signed certificates (or those issued by chains that end in a self-signed certificate) would fail this check.

Validate digital signature with a self-signed certificate

I have a question regarding validation of digital signatures using a self-signed certificate:
The following tutorial works for me:
http://www.oracle.com/technetwork/articles/javase/dig-signature-api-140772.html
However, when a X.509 certificate is self-signed, how can a receiver trust certificate data attached to an XML message? Any one can generate a self-signed cert and claim to be the same sender. The validation in the above tutorial always returns true. Sender’s cert must be loaded to receiver’s truststore, so receiver can use whatever in the truststore to validate signed doc. I cannot find any reference for such a scenario.
Your understanding is correct - with self-signed certificates anyone can create a certificate and signature validation will be ok. The reason is that signature validation performs first of all cryptographic operation, which is completed successfully. The second step is to validate the certificate itself AND also it's origins. When the CA-signed certificate is used, the certificate is validated using CA certificate(s) up to trusted CA (or known root CA). With self-signed certificate validation is not possible. In the above tutorial the procedure of certificate validation was skipped for simplicity as it's quite complex and beyond the scope of tutorial.
The problem you're describing is usually addressed by Public Key Infrastructures (PKI).
This is the traditional model for verifying certificates for HTTPS sites, for example. It starts with a set of trusted Certification Authorities (CAs) from which you import the CA certificates as "trusted". The entity certificates that you get are then verified against this set of trusted anchors by building a certification path between the certificate to verify and a CA certificate you know (linking the certificate to a trusted issuer, perhaps via intermediate CA certificates).
The various rules to do this are described in RFC 5280. The PKI system doesn't apply only to web servers, but to any entity (there are additional rules for web servers to verify that they're the one you want to talk to, on top of having a valid certificate).
(In particular because the choice of which CA certificates to trust is often done on behalf of the user, at least by default, by the OS or browser vendor, this model isn't perfect, but it's the most common in use.)
Alternatively, there's nothing wrong with establishing a list of self-signed certificates you would trust in advance.
Either way, you need to pre-set what you trust by mechanisms out of bands (e.g. by meeting someone you trust and using the certificate they give you in person).
This PKI model goes hand-in-hand with the X.509 format thanks to the notion of Issuer DN and Subject DN. You could have other models, for example relying on PGP certificates, where you would build a web of trust; you would still need an initial set of trusted anchors.
For XML-DSig in Java, you should implement a X509KeySelector that only returns a key that you trust. In a simple scenario, where you have a pre-defined set of self-signed certificates you trust, you can iterate over a keystore containing those trusted certificates. Otherwise, use the Java PKI Programmer Guide (as linked from the tutorial you've used).

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