Self signed certificate for machine to machine https connection - ssl-certificate

I need to set up https communication between a Tomcat application server and a back end system. The web server hosts a public website, so is in a DMZ.
My question is if there any advantage in using official CA certificates, over using self signed certificates in this situation (machine to machine communication)?
I keep hearing self signed certificates should not be used on production systems, but I'm not sure I understand why (for machine to machine communication).

The risk lies in how effective the defenses protecting the hosts in question are, including the network connection between them. Given that weaknesses and exploits are being found all the time, it is reasonable to say there could be issues with self-signed certificates used in a production environment - which includes hosts in a DMZ.
Here's the reason: man-in-the-middle. In short, if either host - or the network between them - becomes compromised, then the traffic between them will still be encrypted, but because the certificate is self-signed, a man-in-the-middle (aka "MITM") would be able to introduce a transparent proxy using a self-signed cert, which will be trusted by both sides.
If instead your hosts use a public CA, then the MITM approach cannot work.
If the annual $15-50 investment per host is more costly than the information on and between them - including what could be on them (e.g., compromised, serving malware), then the choice is simple: don't worry about buying certs. Otherwise, it's important to look into them.
The comment by Adam Hupp on this webpage provides a good, simple scenario:
http://www.vedetta.com/self-signed-ssl-certificates-vs-commercial-ssl-certificates-how-mozilla-is-killing-self-signed-certificates
And here's a more fleshed out description of the risk:
http://blog.ivanristic.com/2008/07/vast-numbers-of.html
And finally a balanced look at the two scenarios, though this article only considers self-signed OK when there is a fully-functional, properly protected and implemented Certificate Authority server installed:
http://www.networkworld.com/news/tech/2012/021512-ssl-certificates-256189.html

I see no advantage in using official certificates for this task - besides the fact that your marketing dept. could claim your infrastructure is "100% certified by $CA". Encryption algorithm/strength and cert duration can be the same, depending on how you configure it.
The recommendations you hear probably focus on the far more common usage of HTTPS for communication with browsers, which nowadays complain about self signed certs. For data transfer between servers, I think it's good practice to encrypt traffic the way you plan on doing it!

Related

TLS Recommendations

I have a product I would like to sell. This product is broken into two physical devices and follows the client server architecture. One device is the server and the other is the client. I am looking to use TLS to secure connection between the server and client.
I would like to setup a server side TLS. I have done research on how to accomplish this with openssl. My strategy at the moment is as follows
create a CA cert
create a Server cert
sign the server cert with the CA
Here's where I struggle to find a solution. I need to support a solution where the two devices do not have access to the internet.
how do I share my CA with clients to complete TLS handshake? To my understanding TLS uses third party to authenticate the cert so you would need internet access if i signed my certs with a CA company
if I share CA with cleint device at production. This works for initial installs but what about once CA cert expires and I need to renew it. Do I just use an API call to get CA from the server. do I have to physically add to the machine every time. Is there any best practices.
lastly is it bad practice to regenerate the CA cert say every 90 days from a script running on the device running the server.
If you only have two devices, and control both, using some kind of shared secret (PSK) between the two devices is likely a lot more convenient and safer that half assing an ersatz PKI. Just make sure it's a different, random, PSK per device pair, and that the owner can actually change them. This is doable with TLS using a PSK suite (see RFC 5489 for TLS 1.2, RFC 7905 for TLS 1.3), but something like IPsec or Wireguard is also perfectly doable.

Automated ACME subdomain SSL certificate generation for resources on different IP addresses

I've been investigating the possibility of migrating to using Let's Encrypt to maintain the SSL certificates we have in place for the various resources we use for our operations. We have the following resources using SSL certificates:
Main website (www.example.com / example.com) - Hosted and maintained by a 3rd party who also maintains the SSL certificate
Client portal website (client.example.com) - IIS site hosted and maintained by us on a server located in a remote data center
FTP server (ftp.example.com) - WS_FTP Server hosted and maintained by us on a server located in a remote data center
Hardware firewall (firewall.example.com) - Local security appliance for our internal network
Remote Desktop Gateway (rd.example.com) - RDP server hosted and maintained by us on a server located locally
As indicated above, the SSL certificate for the main website (www) is maintained by the 3rd-party host, so I don't generally mess with that one. However, as you can tell, the DNS records for each of these endpoints point to a variety of different IP addresses. This is where my inexperience with the overall process of issuing and deploying SSL certificates has me a bit confused.
First of all, since I don't manage or maintain the main website, I'm currently manually generating the CSR's for each of the endpoints from the server/service that provides the endpoint - one from the IIS server, a different one from the RDP server, another from the WS_FTP server, and one from the hardware firewall. The manual process, while not excessively time-consuming, still requires me to go through several steps with different server systems requiring different processes.
I've considered using one of Let's Encrypt's free wildcard SSL certificates to cover all four of these endpoints (*.example.com), but I don't want to "interfere" with what our main website host is doing on that end. I realize the actual certificate itself is presented by the server to which the client is connecting, so it shouldn't matter (right?), but I'd probably still be more comfortable with individual SSL certificates for each of the subdomain endpoints.
So, I've been working on building an application using the Certes ACME client library in an attempt to automatically handle the entire SSL process from CSR to deployment. However, I've run into a few snags:
The firewall is secured against connections on port 80, so I wouldn't be able to serve up the HTTP-01 validation file for that subdomain (fw.example.com) on the device itself. The same is true for the FTP server's subdomain (ftp.example.com).
My DNS is hosted with a provider that does not currently offer an API (they say they're working on one), so I can't automate the process of the DNS-01 validation by writing the TXT record to the zone file.
I found the TLS-ALPN-01 validation method, but I'm not sure whether or not this is appropriate for the use case I'm trying to implement. According to the description of this method from Let's encrypt (emphasis mine):
This challenge is not suitable for most people. It is best suited to authors of TLS-terminating reverse proxies that want to perform host-based validation like HTTP-01, but want to do it entirely at the TLS layer in order to separate concerns. Right now that mainly means large hosting providers, but mainstream web servers like Apache and Nginx could someday implement this (and Caddy already does).
Pros:
It works if port 80 is unavailable to you.
It can be performed purely at the TLS layer.
Cons:
It’s not supported by Apache, Nginx, or Certbot, and probably won’t be soon.
Like HTTP-01, if you have multiple servers they need to all answer with the same content.
This method cannot be used to validate wildcard domains.
So, based on my research so far and my environment, my three biggest questions are these:
Would the TLS-ALPN-01 validation method be an effective - or even available - option for generating the individual SSL certificates for each subdomain? Since the firewall and FTP server cannot currently serve up the appropriate files on port 80, I don't see any way to use the HTTP-01 validation for these subdomains. Not being able to use an API to automate a DNS-01 validation would make that method generally more trouble than it's worth. While I could probably do the HTTP-01 validation for the client portal - and maybe the RDP server (I haven't gotten that far in my research yet) - I'd still be left with handling the other two subdomains manually.
Would I be better off trying to do a wildcard certificate for the subdomains? Other than "simplifying" the process by reducing the number of SSL certificates that need to be issued, is there any inherent benefit to going this route versus using individual certificates for each subdomain? Since the main site is hosted/managed by a 3rd-party and (again) I can't currently use an API to automate a DNS-01 validation, I suppose I would need to use an HTTP-01 validation. Based on my understanding, that means that I would need to get access/permission to create the response file, along with the appropriate directories on that server.
Just to be certain, is there any chance of causing some sort of "conflict" if I were to generate/deploy a wildcard certificate to the subdomains while the main website still used its own SSL certificate for the www? Again, I wouldn't think that to be the case, but I want to do my best to avoid introducing more complexity and/or problems into the situation.
I've responded to your related question on https://community.certifytheweb.com/t/tls-alpn-01-validation/1444/2 but the answer is to use DNS validation and my suggestion is to use Certify DNS (https://docs.certifytheweb.com/docs/dns/providers/certifydns), which is an alternative managed alternative cloud implementation of acme-dns (CNAME delegation of DNS challenge responses.
Certify DNS is compatible with most existing acme-dns clients so it can be used with acme-dns compatible clients as well as with Certify The Web (https://certifytheweb.com)

New SSL Certificate for each client deployment?

Context:
I have an application that is deployed to each client as a Virtual Machine. The latter is installed by the clients wherever they want (I don't necessarily know the final domain). The application comprises an JBoss Web Server that provides access to a configuration page, protected by SSL. Right now the server is using a self signed Certificate. However, I want the browsers to stop showing the warning messages associated to self signed certs. Moreover, I provide a free version of the application that has basic functionality.
Question:
For cases where the client is using a free version (and me wanting to reduce costs), what is the best approach when using a SSL cert, and not knowing the final domain (most of the time)?
It is acceptable to use a self-signing cert? If so, a different one
per client install?
Is it best to issue a new cert (maybe a free one) for each
deployment?
Is is acceptable to use the same cert, signed by a proper CA, on all
of the deployment VMs?
A completely different approach?
Thanks guys!
It is acceptable to use a self-signing cert? If so, a different one per client install?
Ask your clients. Will they put up with a browser warning? or not?
Is it best to issue a new cert (maybe a free one) for each deployment?
It is best for the client to acquire his own SSL certificate. You can't do that for him. Nobody can.
Is is acceptable to use the same cert, signed by a proper CA, on all of the deployment VMs?
No, it entirely defeats the purpose. The certificate and the private key it wraps are supposed to uniquely identify the holder.
A completely different approach?
Handball the whole megillah to the clients. Self-identification is their problem, not yours.

SSL certificate for intranet web servers

I'm interested to purchase a wild card SSL certificate for my public domain (say example.com), so that we can run intranet web servers using a universally recognized CA (e.g., GoDaddy). I do plan to publish the DNS names publicly (e.g. internal.example.com), but their IP addresses are actually LAN addresses (e.g., 192...*). We want to use public DNS, because these web servers may actually be development laptops which travel around, and thus we will use Dynamic DNS to update. It's our intention that these web servers will only be available on the LAN each one is currently running on.
Will that work universally with all clients, e.g., TLS v1.2 ?
Thanks.
As long as the clients can route their traffic to these IP addresses, it will work (otherwise you won't get the connection, of course).
Certificate verification relies on two points:
Verifying that the certificate is genuine, trusted and valid in time.
Verifying that the identity of the certificate matches what you were looking for (host name verification).
This does not depend on how the DNS resolution mechanism. These mechanisms are also orthogonal to the SSL/TLS specifications (although they do recommend to verify the remote party's identity).
I've seen this sort of setup used on various clients and platforms (IE, Chrome, FF, Java clients on Windows/Linux/Mac) and it worked fine.
Of course, whether all implementations do this well is hard to guarantee. There might be some implementation that thinks it's a good idea to perform a reverse DNS lookup, for example.

Can I reuse SSL certificate on a local machine with the same (locally configured) URL?

Here's a possible scenario.
Let's say I have a website "https://www.mywebsite.com" and there is a valid SSL certificate purchased for this domain.
I want to "mimick" this website on my LOCAL machine for a testing purpose.
So let's say I set up a locally-configured "https://www.mywebsite.com" (which is in essence https://localhost/mywebsite or something similar).
Would I be able to re-use the SSL certificate on my local testing website?
You can re-use your SSL certificate if you configure your DNS so that your test machine is the same domain name as server, which is probably a bad idea.
You can also re-use it on your test machine if you don't mind clicking the box "accept this whacked out ssl cert"... So I suppose that the answer is technically yes, although I wouldn't personally do it.
It depends what you are trying to test and why you need a certificate for testing.
If you use the certificate, it will correctly encrypt connections using SSL, but any client will get a certificate mis-match error. If you use a self-signed certificate instead, most clients will give you a warning about that, so it might be just as annoying or not.
If you are testing, for instance, a deployment script to make sure everything gets installed in the right place, it will work. If you are testing to make sure your code correctly redirects a non-secure connection to a secure one, it will work.
If you want to test the your website for functionality, usability, bugs, etc. then your testers will likely complain about the certificate warnings or errors, and you're probably better off doing something else.
I am not sure since the SSL certificate is bound by the domain name that was registered with the certificate. But you may be able to dupe the certificate by editing your hosts file to change localhost 127.0.0.1 to be mysite.com 127.0.0.1, ...in theory at least...if not this is a question for serverfault.com.
Hope this helps,
Best regards,
Tom.
You can't use it since the SSL cert is tied to the domain www.mywebsite.com unless you do a bit of trickery.
You can put an entry in your hosts file saying that domain is at 127.0.0.1, but that's not ideal as you could no longer reach the website.
If you just need a valid cert to test with, then a better alternative is to self-sign using the IIS Resource Kit.
I'm no expert on DNS, but this would introduce a pretty major vulnerability.
Basically if this was allowed, DNS poisoning could be used defeat the whole purpose of third party trust.
Think about it:
I infect your computer so that when you go to www.amazon.com it resolves www.amazon.com to a different domain. That domain uses amazon's ssl cert to fool you into thinking it's legit, so you send me your credit card information.
So, the answer to your question is, no you can't do this. You will still get errors, My guess is that somewhere on the verfication chain, it compares the domain that initiated the request with what its internal dns resolves the domain, to verify there is a match.
As others have said, you can test SSL with a Self Signed Cert, you just have to instruct your testers to import the cert, or go through the trouble of building your own trusted CA, and have testers add that CA as a trusted CA.
There is no point in stealing another sites SSL Cert.
Of course you could use the vulnerability in MD5 to create your own valid SSL cert.
http://www.digicert.com/news/2009-01-05-md5-ssl.htm