Can I use a company's timestamping server with self-signed certificates? - certificate

I'm interested in signing my Silverlight XAP with a self-signed certificate, so it can auto-update. I haven't tried yet, but figure I can create a certificate easily with this question/answer I found on StackOverflow.
But it's not clear to me what the timestamp server does and can I use a timestamp server from a company (for example, the one from Comodo), even if I didn't buy a certificate from them, but self-signed my certificate?

Putting bits and pieces together I found the following answer by BruceCran:
Any timestamp server can be used: I recently switched from my issuer's
timestamp server to Verisign since I found that GlobalSign's server
was unreliable. Furthermore, Thawte don't run their own timestamp
server but recommend people to use Verisign's.
So, yes I assume I can use any timestamp server.
As for what a timestamp server does, it is explained by Comodo:
Since key pairs are based on mathematical relationships that can be
cracked with a great deal of time and effort, it is a well-established
security principle that a digital certificate should expire. Your
Digital ID will expire one year after it is issued. However, most
software is intended to have a lifetime of longer than one year. To
avoid having to resign software every time your certificate expires,
companies have introduced time stamping services. When you sign code,
a hash of your code will be sent to Certification Authority to be time
stamped. Once your software has been time stamped, you will not need
to worry about resigning code when your Digital ID expires. Microsoft
Authenticode allows you to time stamp your signed code so that
signatures will not expire when your certificate does.
So your certificate expires, but your code doesn't.

Related

Managing rollover with Saml 2 metadata

We are trying to implement a smooth rollover for our saml 2 service provider signing certificates.
We have created new certificates with a notBefore at the date of the rollover in the future. Those certificates are exposed on our metadata endpoint, along the certificates currently used to sign saml messages. They are not yet valid since the notBefore property is in the future. Our service provider will start using them when they become valid.
However some partners are having issues with their identity providers complaining that the new certificate is not yet valid.
So my question is the following: are we allowed to expose future certificates that are not yet valid? If not, how are we supposed to manage the signing certificate rollover in saml 2?
Unfortunately the SAML specification doesn't address how certificate roll over should be handled. Therefore, there's no consistent approach.
What you're doing seems reasonable but then I can also understand why some partners would complain about a certificate that isn't (yet) valid.
Some providers simply update their published SAML metadata at the time of certificate roll over. In other words, the metadata contains the current certificate only rather than any past or future certificates. This then places the onus on the partners to ensure they monitor the metadata and switch the certificate immediately.
Of course, this isn't always practicable. In my experience, it's usually best to communicate with the partners that the certificate will roll over on a certain date and provide them with the new certificate and/or metadata prior to that date. Partners should handle signatures generated by either the new or old certificate for an interval of time around the roll over date to ensure a smooth transition. On the roll over date, you'd also publish the new metadata.
You'd probably want an overlap between the old certificate's NotAfter and the new certificate's NotBefore.

How to sign data with certificate on web page

The Stage
I'm working on a web application to enable trade of assets between different parties.
The different parties are known to me, and are not too many.
I record each transaction of an asset from one party to another in a database (sql server). I've stripped down database access as much as I can, and parties have to identify themselves by usernames and passwords to initiate transactions. Communication from web to api will of course be secure (https).
The Problem
These measures leaves me pretty confident that the stored transactions are authentic, but of course the parties of the transactions does not necessarily trust that I (or anyone else with sa password) haven't tampered with the data or created fake transactions.
My thinking
So I figure I need something to be able to prove the authenticity of such a transaction.
Maybe a signature from the party who is giving away their asset? A signature that I can store along with the signed transaction? In that case, the signer needs a private key and I think certificates is a way do this, right? I don't know of any way to access certificates installed on a computer from a web page though so the web page would have to launch a locally installed application to do the actual signing, because the locally installed application could access the certificate, and the signing party have trust in this application to sign the actual untampered-with transaction.
Is this a feasible solution?
How should certificates be distributed? I guess they should be issued from a CA that both I and the party trust?

Whats the impact of server ssl certificate expiration on client application?

I'm consuming a soap service from a server that uses ssl certificate. Although I don't have any dependency on the server certificate in my code, but what if the server certificate gets expired? Will the communication between the server and my client be OK?
In general: no, the communication will not be OK.
A certificate is an endorsement, by the issuer, that the requester has met the identity (and other) requirements that the issuer has put in place; and that the public key in the certificate really is associated with the subject.
The expiration date for the certificate exists because the longer ago the verification process was, the more likely it won't hold up anymore. Imagine you bought awesomesauce.example.com, and got a TLS server certificate for it, and the cert had no expiration. After a year you forget to pay your registrar and lose the name. Someone else comes along, buys it, and has a popular website there. You realize that you have a certificate that identifies you as that site, so you sell it for a million BTC to some hacker group who uses it to do various identity theft tricks and ...
This is similar to an expiration on a driver's license. Maybe your eyesight has dropped below the acceptable thresholds and you shouldn't drive. Maybe you moved and the address on the card should no longer be trusted. Slap an expiration date on there and you now have to reaffirm the facts therein.
You can get an idea of how your client will handle expiration by making a request to https://expired.badssl.com/. If it works, you're trusting outdated claims. If it doesn't: be happy about your client doing the right thing.

x509 certificate for only one application - which OIDs to choose

I'm creating application that will create certificates for users. I want to mark somehow those certificates so that later I can search them in windows user certificate store by following categories:
application GUID (or name - I want to know that this cert is for my application)
certificate role (administrative certificate or user certificate)
user email
I know that for the last one I should use "E = J.Doe#mail.com" or OID number "1.2.840.113549.1.9.1 = J.Doe#mail.com"
But I don't know which OIDs to choose for application GUID and certificate role.
Or maybe I should use "Key Usage" field?
I don't know if it's important, but certificates will be used to authenticate to my application and to decrypt data in database.
Are there any standard ways to do it ?
Hmm... so what I'm thinking is that you plan to issue certificates to each user and you plan to make a different certificate for each application. So if you had 10 users using 3 applications each, you'd be making 30 certificates.
And then the certificate also describes the user's role within the application, and the users's email.
To tell you the truth, I wouldn't put all this information in a certificate. PKI is hard to provision - users generally have difficulties setting up certificates, and reissuing certificates is a pain. Generally, PKI deployment strategies try to minimize the number of certificates that must be issued, balancing that with risk.
The most typical scenario I've seen is that a user is given a single certificate which he uses to identify himself. The certificate includes the user's name, and his email. But it doesn't usually include the user's role or the specific application. Instead, this information is managed on an access control server, that is queried when the user accesses the system. That way, the roles and applications available to the user can be changed without having to reissue the certificate. Products like Active Directory, or Select Access do this sort of thing.
The reason to separate into a separate cetificate per usage is to specifically control some type of risk. For example, if a single user where doing a high-risk operation on one machin and a low risk operation on another, more potentially risky machine, there would be a case to have two certificates (one for each machine) so you could revoke the low-risk certificate without disabling the high risk functions. If you plan to store all the certificates on the same machine, it would be easier to only distribute one certificate per user.
That said - if you still see a need to issue 1 cert per user per application per role, I'd recommend finding a way to jam the application GUID, role and email into the Distinguished name.
You won't get much mileage out of Key Usage or Extended Key Usage - these have very specific value and I doubt that they will convey the information you want to describe. Also, they are used in particular ways by various other applications, so if you need to integrate with other things, that could get tricky.
OK, after few hours I came with something like this.
All Certificates will be recognized by Subject field.
For Administrator certificate it will look like this:
CN=<My application Name> Administrator,OU=Administrator,OU=<My application Name>,O=<My company Name>
and for users
E=<User email>,CN=<User email>,OU=User,OU=<My application Name>,O=<My company Name>
If someone has better idea, I'm open for suggestions :-)
Your task is a quite complex task. To solve it the best way is to put on work a little internal certification authority with openssl. Keep in mind that PKI assigned to the entities you referred the following rule:
Distinguished name: it is used to identify the user or entity to witch the certificate is issued. It's no properly correct to use it for identify two different entity within a single certificate: your user and the application. The two entities shuold be identify in two distinct place.
Key Usage is a bit field with 8 digit that defines the usage of the key. Every bit has its predefinited meaning and cannot be used for other purpose.
I suggest to you to:
Put the application GUID as x509 extension. You can assign and personal OIDs to that exension and query for it. If you OIDs is use internally you can utilize whatever value you want. If you plan to distribuite your certificat eyou can obtain your own OID from IANA
Put the mail in the fields subject alternative mail, as suggested by PKI.
For the aministrative or user you can add a second x509 extension or create a tree of certificate. The main CA certificate, the admin CA certificate and the user CA certificate. Every certificate for admin will be signed by the admin CA, every user certificate by the user CA.

How to securely communicate with server?

I'm building a solution consisting of an app and a server. Server provides some methods (json) and the app uses them. My aim is to make those API methods inaccessible to other clients. What is the best way to do so?
Should I take a look at certificates (to sign every outgoing request)? If yes, where do I start and what is the performance impact of doing so?
What are alternatives?
Put another way, you need a way to distinguish a valid client's request from an invalid client's request. That means the client needs to present credentials that demonstrate the request comes from a valid source.
SSL certificates are an excellent way to assert identity that can be validated. The validity of an SSL certificate can be confirmed if the certificate contains a valid signature created by another certificate known to be secure, a root cert. As noted in other answers an embedded certificate won't do the job because that certificate can be compromised by dissecting the app. Once it is compromised, you can't accept any requests presenting it, locking out all your users.
Instead of one embedded app cert, you need to issue a separate certificate to each valid user. To do that, you need to set up (or outsource to) a Certificate Authority and issue individual, signed certificates to valid clients. Some of these certificate will be compromised by the user -- either because they were hacked, careless or intentionally trying to defraud your service. You'll need to watch for these stolen certificates, place them on a certificate revocation list (CRL) and refuse service to these compromised certificates. Any web server is able to refuse a connection based on a CRL.
This doesn't solve the security issues, it just moves them out of the app. It is still possible for someone to create what appears to be a valid certificate through social engineering or by stealing your root certificate and manufacturing new signed certificates. (These are problems all PKI providers face.)
There will be a performance hit. How much of a hit depends on the number of requests from the app. The iPhone NSURLConnection class provides support for SSL client certificates and client certificates can be installed in the phone from an e-mail or authenticated web request. Managing the infrastructure to support the client certs will require more effort than coding it into the app.
Incidentally, voting down any answer you don't like creates a chilling effect in the community. You're not nearly as likely to get advice -- good or bad -- if you're going to take a whack at everyone's reputation score.
I will now freely admit that it's an interesting question, but I have no idea how it could be done.
Original answer:
Interesting question. Assuming people can't reverse-engineer the iPhone app, the only solution that comes to mind would be to sign requests with a public key, or some other secret known only to the application. By that, I mean adding an extra argument to every API call that is a hash of the destination URL and other arguments combined with a secret known only to your server and application.
To expand upon this: suppose your API call has arguments foo, bar and qux. I would add a signature argument, the value of which could be something as simple as sorting the other arguments by name, concatenating them with their values, adding a secret, and hashing the lot. Then on the server side, I would do the same thing (excepting the signature argument) and check that the hash matches the one we were given in the request.
Consider authenticated HTTP.
For a cheaper alternative, there's shared secret/hash scheme. The client and the server have a shared secret string of text. Upon request, the client hashes together (using MD5, or SHA1, or SHA something else - you choose) the request fields and the secret. The hash value is attached to the request - say, as another POST field.
The server does the same operation with the request and with its copy of the secret, then compares the hash values. If they don't match - service denied.
For added security, you may encrypt the hash with a RSA public key. The client has the public key, the server keeps the private key. The server decrypts the hash with the private key, then the same. I did that with a C++ WinMobile client and a PHP-based service - works like a charm. No experience with crypto on iPhone, though.
UPDATE: now that I think of it, if we assume that the attacker has complete control over the client (ahem jailbroken iPhone and a debugger), the problem, as formulated above, is not solvable in theory. After all, the attacker might use your bits to access the service. Reverse-engineer the executable, find the relevant functions and call them with desired data. Build some global state, if necessary. Alternatively, they can automate your UI, screen scraper style. Such is the sad state of affairs.