Shipping SSL certificate in Mac OS X app - macos

I'm writing a utility Mac OS X app that basically acts as a web server accepting incoming HTTP requests (think of it as a mock REST API server). I want to be able to support HTTPS, but ideally I'd like to remove the requirement for my users to have to purchase their own SSL certificates.
I've been thinking a little on how I might achieve this. Let's say I register a domain called myapp.com. I then purchase an SSL cert for myserver.myapp.com that is signed by a registered CA. I ship my app with those SSL cert details embedded within it. All my users have to do is update their /etc/hosts file to point myserver.myapp.com to whatever IP address my app is installed and running on.
In fact, by far, the most common scenario would be my app running on the same machine as the client, so I'm considering updating the main DNS entry for myserver.myapp.com to point to 127.0.0.1, and most users wouldn't have to change anything.
So, that's the basic theory. What have I missed that would make this an unworkable plan? A couple of things that have crossed my mind:
I could use a self-signed cert. However, many SSL clients barf (or throw up warnings) if the cert doesn't have a valid CA chain. I'm happy to pay the money for a real cert to alleviate this inconvenience for my users.
I would be embedding the private key for my SSL cert into my app. In theory, someone could extract that and use it to impersonate my app. I guess my reaction is "so what?" My app is a small productivity app, it isn't an e-commerce site. It doesn't collect sensitive info. It literally just simulates web server responses so devs can test their apps.
Any advice/feedback would be greatly appreciated. Thanks.

This won't work - but for nontechnical reasons.
Distributing an SSL certificate to your users along with its associated key will violate the issuance terms of your SSL certificate provider, and they will revoke the certificate when they discover what you have done. (This happened, for example, when Pivotal tried to offer SSL service for developers through sslip.io.) This will, of course, cause your application to stop working.
If your users have administrative access to their machines, they can create and trust their own self-signed CA using Keychain Access. Once they have done so, they could create a certificate (again, using Keychain Access) and insert that into your application to enable SSL.

As said in the other answer you can't ship the same certificate for everybody. What you could do is generate different for everybody:
The application ask them the domain name they want to use (a domain they must own, like myapp.example.com)
The application use the ACME protocol to get automatically a trusted certificate from let's encrypt
Note: you can provide them subdomains of a domain you control (like [clientid].yourappname.yourdomain.com) ONLY of you can register yourappname.yourdomain.com in the public suffix list (because let's encrypt have rate limits)

Related

Guzzle disabling certificate verification to false, how insecure is it?

Recently I found myself working with Guzzle while making requests to another server to post and fetch some data, in some cases, tokens. But I was getting certificate invalid error and I even tried to get a new .pem certificate, but Guzzle was still not accepting and kept throwing that error. So finally, I did what the "Internet" said:
$guzzleClient = new Client([
'verify' => false
]);
Now although this solution works, I am not sure how insecure it can get. Do I need to worry? If yes, in what scenarios?
well this is a big problem if you are for example
having login system on the request you are sending using guzzle
having payment/checkout on the request
basically any sensitive data being passed to the other server
because when you pass data without SSL certificate then your requests might get caught by malicious programs like
BurbSuite / WireShark , cain and abel / EtterCap
as these programs are Sniffing programs and anyone can get a version from the internet as they are open sourced and every thing going without SSL can be intercepted by the hacker using the tools mentioned above and the hacker can look to the entire request in plaintext! so its highly recommended to use SSL connection when passing sensitive data
Worth Mentioning : now a days even SSL isn't very secure because hackers can remove it using SSLStrip tool but believe me SSL will make it much harder for them to get to your request because if they used it your website sometimes will make non-completed requests and it will notify the user that the network isn't secure this will make it very hard for the hacker to get the user's data,
TLS/SSL in common configurations is meant to give you three things:
confidentiality - no third party is able to read the messages sent and received,
integrity - no third party is able to modify the messages sent and received,
server authentication - you know who are you talking to.
What you do with setting verify to false is disabling the certificate verification. It immediately disables the server authentication feature and enables loosing confidentiality and integrity too when facing an active attacker that has access to your data stream.
How is that?
First of all TLS/SSL relieas on Public Key Infrastructure. Without going into too much details: you hold on your machine a set of certificates of so called Certification Authorities (CA) whom you trust. When you open a new communication to a service, you get the services certificates and in the process of verification you validate amongst other things if the certificate belongs to a CA you trust. If yes, then the communication may proceed. If no, then the communication channel is closed.
Attack patterns
Disabling certificate verification allows for Man-in-the-Middle (MitM) attacks than can easily be performed in your local network (e.g. via ARP poisoning attacks), in the local network of the service you are calling or in the network between. As we usually do not trust the network completely, we tend to verify.
Imagine me performing an attack on you. I have performed ARP poisoning, now I can see all your traffic. It's encrypted, isn't it? Well, not obviously. The TCP handshake and TLS handshake you believe you have performed with the target service - you have performed with me. I have presented you not the certificate of the target service, as I am unable to fake it, but my own. But you did not validate it to reject it. I have opened a connection between me and the target service on your behalf too so I can look into the decrypted traffic, modify if necessary and reply to you to make you believe everything is ok.
First of all - all your secrets are belong to me. Second of all - I am able to perform attacks on both you and the target service (which might have been secured by authentication mechanisms, but now is not).
How to fix this?
In XXI century there should be little reason to disable TLS verification anywhere. Configuring it to work properly might be a pain though, even more when you are doing it for the first time. From my experience the most common issues in the micro service world are:
the target certificate is self-signed,
you are missing a CA root certificate in your trust store,
the microservice does provide his certificate, but does not provide an intermediate CA certificate.
It's hard to guess what your issue is. We would need to dig deeper.
While the other answers points out some really good point about how important SSL/TLS is, your connection is still encrypted and the remote endpoint you're using has https:// in it as well. So you're not entirely disabling SSL when you set verify to false if I'm not mistken. It's just less secure since that you're not verifying the certificate of the remote server if they are signed by a Certificate Authority (CA) using the CA bundle.
Do you need to worry?
If this is something on your production, ideally you'd want things to be secure and configured correctly, so yes.
By not verifying the certificate, like Marek Puchalski mentioned, there's possibility of the server might not be the one you think it is and allows mitm (man in the middle) attack as well. More about mitm here, and peer verification here.
Why is it happening & how do you fix it?
Most common issue is misconfigured server, especially PHP configuration. You can fix your PHP configuration following this guide, where you'll be using adding the CA root certificates bundle to your configuration. Alternatively you can add this to Guzzle.
Another common issue is, the remote server is using a self-signed certificate. Even if you configured your CA bundle in your trustedstore, this certificate can't be trusted since it's not signed by a trusted CA. So the server needs to configure a SSL certificated signed by a CA. If that's not possible, you can manually trust this CA root, however this comes with some security concerns as well.
Hope this helped :)

From self managed Let's Encrypt to AWS Certificate Manager

I have been managing Let's Encrypt's SSL certificates for a domain.
Now I am moving to Amazon API gateway. I will be using the AWS Certificate Manager to generate HTTPS certificates for the root domain and a bunch of subdomains.
If I make the transfer, what happens to my current HTTPS certificate which is associated with my domain. If browsers suddenly start seeing a new HTTPS certificate for a domain, for which they had been getting a different HTTPS certificate until now, would this be a problem?
Also, once I make the shift, what do I do with my current (manually managed) Let's Encrypt certificate? Is there a way to permanently void it?
Szabolcs Dombi says
You can have multiple valid certificates for the same domain at the
same time. Moving from one certificate issuer to another should not
cause a problem.
Toby Osbourn says
SSL certificates don’t last forever, most of them need to be renewed
on a yearly cycle and occasionally you will want to change the type of
the SSL certificate mid-cycle.
Since you are replacing certificates, I suggest you to back up the ones you have.
Once you have backed up the old certificates, just overwrite the .crt and .key files with your new ones. Then, reload your web server so it knows to look at these new certificates, and you should be good to go.
If it's within your interest to know more about how to Generate SSL certificate using Amazon Certificate Manager (ACM), I suggest Barguzar, A. (July 2018). Building Serverless Python Web Services with Zappa. where one can read a good step by step guide. See an excerpt of it below:
ACM is a service that manages and creates SSL/TSL certificates for
AWS-based services and applications. An ACM certificate works with
multiple domain names and subdomains. You can also use ACM to create a
wildcard SSL.
ACM is strictly linked with AWS Certificate Manager Private
Certificate Authority (ACM PCA). ACM PCA is responsible for validating
the domain authority and issuing the certificate.
You can have multiple valid certificates for the same domain at the same time. Moving from one certificate issuer to another should not cause a problem.
This also means that if you create a new certificate the old one still can be used unless it already expired.

Does updating SNI config affect SSL Certificates and Validation

I'm developing an app for a non-tech client that has outsourced the backend to another developer. We'll be launching the app under 7 different branded app, over a series of weeks. Each app is exactly the same, sans for the domain the API end points are on (IIS hosted).
As part of our security, we validate the SSL certificate when we connect to the API, and ensure the key returned by the API server matches our hardcoded version of it, as to prevent man-in-the-middle attacks to sniff our REST calls. We have this functioning now for the current server (1 of 7 to be rolled out).
We've asked the backend guys to provide the certificates for the remaining 6 sites, so we can deploy the apps with the expected keys. However, they claim that as they will be rolling out the sites individually over the coming weeks, each time they bring a new a new site online, they said they are "updating the SSL certificate" which is required as they are "using SNI on the server, so each time a new site is added, the certificate will change, and the hardcoded validation for the existing sites will break".
Now whilst I'm no dummy, I'm also not a server admin, and only 99.9% sure that the SNI configuration to support another cert on the server, will not have any affect on the current certs already hosted for the existing domains. As a result, I wanted to explicitly confirm that the cert key we're validating as part of the SSL auth, is not going to change with each revision of the SNI config. The backend devs have essentially shut us down claiming we're paranoid, and going "beyond what is required" and to not expect "the same security a the major players offer" (as I mentioned that any decent commercial app validates its connection).
Is anyone able to confirm (or correct) my understanding of SNI as it relates to the certs, primarily that as they bring new sites online, that changes to the SNI have 0 impact on the existing certs for the current sites?
Edit: Whilst the use of multi-domain certs would regenerate the key, we can assume that they could generate/re-issue a multi-domain cert now in advance of the domains coming online. The question of if it's affected by the SNI config remains.
"updating the SSL certificate" which is required as they are "using SNI on the server, so each time a new site is added, the certificate will change, and the hardcoded validation for the existing sites will break".
This is a weird argument. The point of SNI is that they can have multiple sites (domains) on the same IP address where each has its own certificate. If they add a new site only a new certificate for the new domain need to be created and all the other certificates will continue to work: a client using SNI will tell which site it wants to visit and the server then can pick the appropriate certificate. If they instead could not rely on SNI then they would have to use certificates which cover all sites on the same IP address.
So while it can be that they have some process which requires this kind of reissuing certificates it is not a requirement because of use of SNI, but only because they designed their process this way.

Securing communication on a portable intranet (changing IP addresses)

I have the following scenario:
A network will be set up on a Windows infrastructure
A website will be put on that network - It is not given a domain name and is not available on the internet. It will be addressed only via an internally recognised IP address.
A piece of software within that network will communicate with the website
(we want to avoid the 'Could not establish trust relationship issue' found with self-signed certificates without reducing security as, I believe, the accepted answer does).
The website will also be viewed on tablets and PCs.
After a few days, the service will be be put on a different network (with different IPs).
It will installed on many PCs/Networks.
I want to secure this via SSL, but it seems tricky following the 2015 update that disallowed IP addresses to have certificates.
This post suggests going via a public IP, but the solution may be completely offline in an area without internet access.
I've spent hours researching, but seem to be missing something.
How should this be done please?
I would setup a DNS server with an app.local domain that gets issued the certificate.
Even if you serve up the intermediate certificates in the TLS handshake (which you should ALWAYS do and not rely on AIA), verifying the chain becomes problematic without Internet access as browsers won't be able to reach the CRL URL (Certificate Revocation List). That is, of course, unless we're talking about your own CA (living in the same network) that issues the site certificate.
If everything you describe runs in a well guarded sandbox then you probably don't need the TLS layer at all, ask yourself WHO is the attacker and WHAT are you protecting.

Using the ruby SDK, how can I get an SSL certificate signed for my AWS EC2 instance?

I have created a pem and crt file to use with my EC2 instance on AWS. I have 2 questions here:
1) The configuration instructions say: "Normally, at this stage you would submit your CSR to a Certificate Authority (CA) to apply for a digital server certificate." To whom do I send the certificate and how do I do it? Sorry, first time for me.
2) I am horribly confused about the uploading process to AWS. I have seen articles on uploading to a load balancer and uploading to IAM. I am using an EC2 instance and not, as far as I know a "load balancer" and I do not use IAM security. So how should I upload and what do I need to do?
Yours very confused seeking help ...
To get an SSL certificate signed you need to submit it to a trusted company, known as a Certificate Authority (CA). Think of your CSR like a blank cheque, nobody will trust it until it's signed by someone trustworthy.
There are commercial CAs which vary greatly in price, alternatively there are free CAs such as CACert (which I haven't used). The general process is: upload your CSR to the CA's site & the CA will provide a signed certificate.
If you want more information on what a CA's role is wikipedia is a great place to start, excerpt below:
In cryptography, a certificate authority or certification authority (CA) is an entity that issues digital certificates. A digital certificate certifies the ownership of a public key by the named subject of the certificate. This allows others (relying parties) to rely upon signatures or on assertions made by the private key that corresponds to the certified public key. In this model of trust relationships, a CA is a trusted third party – trusted both by the subject (owner) of the certificate and by the party relying upon the certificate. Many[quantify] public-key infrastructure (PKI) schemes feature CAs.
For serving SSL traffic you have two options:
A common web pattern is to "Terminate SSL at the load balancer", which just means the load balancer will host and serve the SSL certificate, then simply sends traffic to the web server (your EC2 instance) via http. This is generally considered safe as the last hop is within your infrastructure.
If you want to go without a load balancer you'll need something on the EC2 instance to serve the SSL certificate. Here again there are plenty of options but generally installing Nginx or Apache on your instance to sit in front of your app works well.
Example configuration for Apache & Nginx are plenty & you should be able to find specific instructions for what-ever language & framework you're using but they're all fairly similar.
The play framework doco has examples for both Apache & Nginx sitting in front of a web app running on the same (EC2) server on port 9000 which should work for pretty much anything running on that port.
Plenty of reading to get you on your way, hope it helps!

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