Downside to using *.herokuapp.com domain? - ssl

I need to point thousands of TLDs to the same Rails app hosted in Heroku.
So far I have automated the process of adding domains to CloudFlare and Heroku, but SSL has proven to be a challenge.
Heroku has ACM on by default, which will fail when the CF orange cloud is on (which I need on).
I can't turn ACM off with Flexible SSL in CloudFlare because I need SSL from edge to origin.
I can't use an Origin CA because Heroku only supports 1 certificate per app (not per domain) and I'm going to be well over 100 domains. I also don't want to have to manage multiple certificates which contain multiple TLDs and re-generate the certificate with every single domain in it every time I add a new domain.
Question: Is there a downside to just pointing www and # to my-app.herokuapps.com?
So far it works perfectly from a DNS perspective with Full SSL in CloudFlare, even though it says in Heroku docs that the herokudns.com strategy is encouraged. I just wanted to ensure there aren't any deprecations or hidden limits that will suddenly make this stop working after I've committed to it.
I'm also open to any other solutions.

Related

Heroku Automated Certificate Management (ACM) for app with existing custom domains and certificates

I have an application on Heroku that currently does not use ACM.
Our customers provide us a domain, point their DNS to the provided CNAME, and then provide us a SSL certificate to upload manually.
We would like to cut out the SSL portion as it's a huge burden for people. It appears Heroku ACM can take care of this for us.
My concern is with existing domains / certificates.
What will happen to them if I enable ACM?
I'd imagine they get taken care of with a tiny bit of downtime, but don't want to get into a spot where we've broke their domain and no longer have the certificates they provided us.

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)

Multi-tenant SSL with Cloudflare and Heroku

Im currently building an application that will reside at app.mydomain.com which is running on Heroku. All users will have their own entry points, like app.mydomain.com/client1, app.mydomain.com/client2, etc. I want clients to be able to setup their own domain (www.clientdomain.com) and cname it to their entry point. I understand this is pretty straight forward up until now.
All my DNS is handled by Cloudflare and I believe I can configure Cloudlfare into Full (Strict) mode, all I need to do is install their Origin Cert onto my Heroku dyno. This will ensure that all direct connects to my domain will be secure (going to app.mydomain.com/client1).
Question is, how does a client go about getting an SSL'ed connection for their domain; do I need to get a multidomain cert and start adding domains to it as I get clients, or am i supposed to install their cert onto Heroku (I believe I can only install 1 so thats a no go) or is it supposed to live on Cloudflare somewhere, or are there additional options I'm not seeing (I hope there are!).
Im not wondering what to do for my own domains, but rather, how do clients setup an SSL connection with their domains that resolve onto my servers.
This is rather perplexing!
The flow would be (I think):
User Browser -> Clients DNS -> (cname to) My Cloudflare -> Heroku
Hmm, it looks like this might be a pretty solid solution to this issue...
https://blog.cloudflare.com/introducing-ssl-for-saas/
Edit - after clarification
I'm currently building an application that will reside at
app.mydomain.com which is running on Heroku. All users will have their
own entry points, like app.mydomain.com/client1,
app.mydomain.com/client2, etc. Question is, how does a client go about
getting an SSL'ed connection for their domain; do I need to get a
multidomain cert and start adding domains to it as I get clients?
If you are going to use the same Heroku app for all of your clients (I think this is a bad idea by the way, but you might be required to) - then yes - you should get a multi-domain certificate and keep adding domains to it as your list of clients expand.
Original answer - which explains SSL + Load Balancing on Heroku.
Im currently building an application that will reside at
app.mydomain.com which is running on Heroku. I was clients to be able
to setup their own domain www.clientdomain.com and cname it to mine.
You will need a wildcard certificate to cover your subdomain (for the app.mydomain.com). You'll have use that cert in heroku.
...all I need to do is install their Origin Cert onto my Heroku dyno.
You are correct - except it's not on your Heroku dyno, it's on your Heroku app endpoint. There's a good read here: https://serverfault.com/questions/68753/does-each-server-behind-a-load-balancer-need-their-own-ssl-certificate
If you do your load balancing on the TCP or IP layer (OSI layer 4/3,
a.k.a L4, L3), then yes, all HTTP servers will need to have the SSL
certificate installed.
If you load balance on the HTTPS layer (L7), then you'd commonly
install the certificate on the load balancer alone, and use plain
un-encrypted HTTP over the local network between the load balancer and
the webservers (for best performance on the web servers).
So you should install your SSL certificate to your Heroku endpoint and let Heroku handle the rest.
Question is, how does a client go about getting an SSL'ed connection;
do I need to get a multidomain cert and start adding domains to it as
I get clients, am i supposed to install their cert onto Heroku (I
believe I can only install 1 so thats a no go) or is it supposed to
live on Cloudflare somewhere?
If you're referring to adding servers to your service from heroku, all you need to do is increase the number of web-dynos. Heroku will handle the load balancing in between these dynos. Your SSL certificate should be resolved in the load balancer so your dynos will be serving requests for the same endpoint. You shouldn't need another SSL certificate for the endpoint you've defined - as long as you're serving traffic from multiple dynos attached to it.

How can I get Letsencrypt certificates before adding the server to production

I am trying to lunch new servers automatically when needed but I am having some difficulty getting the certificate before making the server live. What I want to do is run a setup script which gets all the packages, websites and certificates ready and after that add the server to production. However, Letsencrypt wants me to verify that the server requesting the certificate is actually the website which replies to requests. How can I get the Letsencrypt certificate before adding the server to production? I don't want requests to the real website to be routed to the new server until it is fully setup and has the certificates.
One solution I thought of is to save the certificates on an AWS S3 bucket and synchronize them whenever a renewal is needed. Then when I setup a new server I just get the latest certificate from my AWS S3 bucket and I don't have to worry about getting the certificate from the CA until after the server is added to production.But this solution doesn't seem "clean" and would require me to have an S3 bucket just for my Letsencrypt certificate which also adds another weakness where a certificate could be stolen from.
Is there a more simple solution which I haven't thought of yet?
In a load-balanced (LB) scenario, you should consider having exactly one entity responsible for performing LE certificate acquisition. Things get complicated with multiple entities doing this asynchronously - you'd need to be able to guarantee that the ACME challenges get routed to the relevant server(s), and your LB doesn't have that information (without additional complexity).
So I'd suggest either:
Terminating HTTPS at your load-balancer. Then none of your servers need to care about HTTPS or certificates.
Having one "special" server that's responsible for interacting with LE, and then distributing the cert to the other servers. The details of how you do that is implementation-dependent, because it depends on how you're managing server/service configuration.

ssl on custom domain for heroku app

I want to connect a custom domain to an app built on Heroku. Can someone confirm that I actually need to buy a certificate and in addition buy the SSL addon on Heroku?
Do I need both or is one of them enough? What is the point of the addon?
/Knut
If you are already using paid dynos (e.g. Hobby dynos) then you can save some costs by using Heroku SSL for free in your app, instead of paying for the SSL Endpoint add on.
This is assuming your app doesn't need to support really old browsers (see Minimum supported browser versions.
These add ons basically provide the protocol support your app needs for SSL with your private domain.
However, regardless of which of the above 2 you choose, you will still need to acquire in addition an SSL certificate. There are all kinds of different offerings for the actual certificate, including free certificates e.g. from Let's Encrypt.
See here for instructions on using a free Let's Encrypt certificate on Heroku with Heroku SSL.
Bottom line: If you are already using paid dynos, it should be possible for you to add full SSL support for your custom Heroku domain for free.
If however you find the above too bewildering, you might want to pay a few bucks for a service such as Expedited SSL, which gives you a certificate (for a monthly fee) and takes care of the whole issue of installing it and keeping it updated on Heroku.
Heroku has made it even easier to use SSL for custom domains now assuming you're not on the free tier plan (if you pay for at least one dyno you're good to go).
https://blog.heroku.com/announcing-automated-certificate-management
Basically, once you have a paid plan for your app., Heroku will generate the certs for you and any custom domains you have added. Then you need to check that you have the right forwarding setup by your domain provider etc.
To add ssl to an existing app you can run:
$ heroku certs:auto:enable -a <app name>
Then run the following command and make sure your custom domains are returned:
$heroku domains