Why not SSL enable Apache with own CA? - ssl

I purchased a domain name. I set up a website that is deployed on Apache, that is accessible at my domain, currently on http protocol "port 80". I now want to configure this Apache server for SSL. I'm evaluating the below 2 options.
Option #1: I create the "Certificate Signing Request" (CSR), then while acting as the CA, I create the certificate based on the CSR, I then configure Apache to be running on port 443, with the certificate I created.
Option #2: I create the CSR, I submit my CSR to a widely known CA like Symantec to get a certificate. I then configure Apache to be running on port 443, with the certificate provided by Symantec.
What are the downfalls to option #1?
From an end-user perspective "someone accessing my site", what indications would they have that I used option #1?
Is it correct to assume, with option #1, that I couldn't get end-users accessing my site to get a green bar menu?

With option 1 the end user has no confidence they are not being spoofed. Because you are acting as your own CA the end user has to make a decision about whether to trust you. If they do - they may well be trusting someone who has intercepted your request and used their own certificate.
With option 2 the user is trusting the CA that provided your certificate and can be more confident that no man-in-the-middle attack is taking place.
For some purposes your own self-signed cert can be fine. Not for any real ecommerce though.

Related

Using and then removing self-signed certificate localhost

Problem Background:
As part of the Computer Networking course assignment, I have been given task of implementing a Proxy Server ( using python socket and ssl module ) that handles https communications between the browser and the origin server (The real server that my browser wants to talk to).
What I have done so far:
I have implemented the above requirement using ssl sockets and also generated self-signed 'cert.pem' 'key.pem' files.
What I need to do:
Now I just need to tell my browser (chrome 89 on kubuntu 20.04) to accept this self-signed certificate and then test the working of my proxy server.
Reading from this stackoverflow question, I can see that I have to:
(1) become my own CA (2) then sign my SSL certificate as a CA. (3) Then import the CA certificate (not the SSL certificate, which goes onto my server) into Chrome.
My confusion/question:
So if I do this, when eventually I am done with this assignment, how do I reverse all these steps to get my browser in the previous state before I had made all these changes. Also, how to reverse the "become your own CA" and also delete the SSL certificates signed by my CA.
Basically, I want my system to return to the previous state it was before I would have made all these changes.
UPDATE:
I have done the previously outlined steps but now I get an error.
Here is a snippet of my code:
serv_socket = socket(AF_INET, SOCK_STREAM)
serv_socket.bind(('', serv_port))
serv_socket.setsockopt(SOL_SOCKET, SO_REUSEADDR, 1)
context = ssl.create_default_context(ssl.Purpose.CLIENT_AUTH)
context = context.load_cert_chain('cert.pem', 'key.pem')
context.set_ciphers('EECDH+AESGCM:EDH+AESGCM:AES256+EECDH:AES256+EDH')
serv_socket.listen(10)
socket_to_browser, addr = serv_socket.accept()
conn_socket_to_browser = context.wrap_socket(socket_to_browser, server_side=True)
At the last line conn_socket_to_browser = context.wrap_socket(socket_to_browser, server_side=True) an exception is thrown: [SSL: HTTPS_PROXY_REQUEST] https proxy request (_ssl.c:1123)
What am I doing wrong ?
As glamorous as "becoming your own CA" sounds, with openssl it basically comes down to creating a self-signed certificate, and then creating a directory where some CA-specific configuration will be stored (I don't fully remember the specifics, but I think it was just some files related to CNs and serial numbers) so basically reversing the "become your own CA" step is something as mundane as deleting this directory along with the private key and self-signed certificate you were using for the CA. That's it, the CA is no more.
And for chrome returning to the previous state, you would just go the the CA list where you added the CA certificate, select it and delete it. Chrome will stop accepting certificates signed by your CA.
Regarding your new problem... In my opinion, you have developed some kind of reverse proxy (meaning that you expect normal HTTPS requests that you then redirect to the real server) but you have configured Chrome to use it as a forward proxy. In this case, Chrome does not send it a normal HTTPS request, it sends a special non-encrypted CONNECT command and only after receiving the non-encrypted response, it negotiates the TLS connection. That's why openssl says "https proxy request" because it has detected a "https proxy request" (a CONNECT command) instead of the normal TLS negotiation.
You can take a look at How can a Python proxy server (using SSL socket) pretend to be an HTTPS server and specify my own keys to get decrypted data?
It's python, but I think that you'll get the idea

Run same site with two different ssl ports on iis

I have my website https://www.MyWebSite.com running on port 433. But I also have a admin login that only are available from the office local network http://MyServer:9999/Login.aspx. Both addresses points to the same site but different bindings.
Is it possible to get the one on port 9999 to use https? I tried creating a self signed certificate in IIS but my browser still complained, even though I exported the certificate and stored it in my CA Trusted root.
So just to sum everything:
My regular site: https://MyWebSite.com <-- working fine
My admin login, only accessible via local network: http://MyServer:9999/Login.aspx works fine.
When adding a selfsigned certificate issued to "MyServer" (not MyWebSite) and add the new binding on port 9999 I though to the website but Chrome is giving me a warning NET::ERR_CERT_COMMON_NAME_INVALID, even though the cert is Issued To MyServer and are trusted
Is it possible to get the one on port 9999 to use https?
yes it is possible to setup another port with selfsigned
certificate.
Normally Selfsigned certificate will have fully qualified machine name
e.g. machinename.subdomain.domain so you have to browse using https://machinename.subdomain.domain:9999/
Please double check what error you are running into ,In chrome
Your connection is not private
Attackers might be trying to steal your information from in08706523d (for example, passwords, messages, or credit cards). NET::ERR_CERT_COMMON_NAME_INVALID
in IE,you may get
There is a problem with this website’s security certificate.
The security certificate presented by this website was issued for a different website's address.
Security certificate problems may indicate an attempt to fool you or intercept any data you send to the server.
In that case,assuming you have given hostname as * in IIS binding, and also installed the selfsigned certificate installed your "Root Certification Authorities " You should be able to browse to
https://machinename.subdomain.domain:9999/ without any issues

SSL: where is the certificate hosted? when does the verification occurs?

I am quite confused here:
I use DNSMadeeasy to manage my DNS. I have two apps.
One is Heroku hosted, and has https on https://example.com - Heroku has many great tutorials to setup the certificate, it hasn't been a problem.
The other one is a wordpress, hosted in 1and1 (though it shouldn't matter here), and is reachable at http://subdomain.example.com and we want it to be available at https://subdomain.example.com
1and1 does sell SSL certificate, but their automated setup works only when one uses their services for DNS also, as they say. Their support says it should be DNSMadeEasy which should be hosting our SSL certificate. I have the feeling it is not true, because for https://example.com, DNSMadeEasy was never involved.
Questions:
When does certificate querying occurs? Before, After, or in parallel of DNS resolution?
Who is hosting a certificate? The DNS provider? The server (accessible like a sitemap.xml at the root for instance)? A third party?
To enlarge the case, in general if I have a personal server with a fix IP, how can I communicate through https with a valid certificate?
In my case, how can I get my way out of it to make https://subdomain.example.com work?
You are right for not believing the 1and1 suggestion.
To answer your questions:
When does certificate querying occurs? Before, After, or in parallel
of DNS resolution?
A client resolves domain name to an IP address first. So DNS resolution happens first.
Who is hosting a certificate?
The server (in simplistic terms) hosts the certificate.
When a client wants to connect to your site (via HTTPS) it will first establish a secure connection with that IP address on port 443 (this is why usually (without SNI) you can only have one SSL certificate per IP address). As part of this process (which is called handshake) a client can also specify a server name (so-called server name extension) - this is a domain name of your site. This is useful if you have an SSL certificate that is valid for multiple domains.
A good/detailed explanation how it works can be found here
http://www.moserware.com/2009/06/first-few-milliseconds-of-https.html
if I have a personal server with a fix IP, how can I communicate
through https with a valid certificate?
Your server will need to be able to respond on port 443 and have/host an SSL certificate for a domain that resolves to that IP address.
In my case, how can I get my way out of it to make
https://subdomain.example.com work?
You need to purchase a certificate for subdomain.example.com and install it on the wordpress server.
Usually in hosted solution like yours you have 2 options:
Buy the SSL certificate via the provider (1and1 in your case) - a simpler option, they will configure everything for you.
Buy the SSL certificate yourself. Here you will most likely need to login to your 1and1/Wordpress management interface and generate a CSR (essentially a certificate request). Then you purchase the SSL certificate using this CSR and then you can install it via the same management interface.
The process will look similar to this:
http://wpengine.com/support/add-ssl-site/

Cannot perform HTTPS local tunnel fith Fiddler2 - Problems with certificates

I am trying to create an HTTPS-tunnel on my machine. My intention is having all requests to https://localhost:8888/<something> (the port where Fiddler is listening to) be directed to https://myserver.net/<something>. I am using the following script as per Fiddler doc:
static function OnBeforeRequest(oSession: Session) {
// <Fiddler 2 preexisting code>
// HTTPS redirect -----------------------
if (oSession.HTTPMethodIs("CONNECT") &&
(oSession.PathAndQuery == "localhost:8888"))
{
oSession.PathAndQuery = "myserver.net:443";
}
if (oSession.HostnameIs("localhost"))
oSession.hostname = "myserver.net";
// --------------------------------------
// <Fiddler 2 preexisting code>
}
Also in Fiddler settings I checked the decryption check and installed certificates as you can see in the image below:
I restart Fiddler, it prompts me to install its fake certificates, I agree. I can see the certificate in my Windows Certificate System Repository when using certmgr. It is a self-signed certificate.
So What I do is opening a browser and type: https://localhost:8888/mypage.html, and what I get is an error. Internet Explorer reports this:
Error: Mismatched Address. The security certificate presented by this
website was issued for a different website's address. This problem
might indicate an attempt to fool you or intercept any data...
When I get certificate info (basically the certificate presented by the contacted host is being rejected, the same certificate can be displayed), I can see that the rejected certificate was issued by Fiddler and the subject is myserver.net.
So the certificate is ok because it is certifying myserver.net, I see that the problem is that probably my browser was expecting a certificate whose subject is localhost. Is it true?
How to handle this situation?
Assumption
I can understand that the problem is a certificate being issued for a website which I did not ask for. So the solution would be using a certificate certifying localhost:8888?
A certificate is valid if it is directly or indirectly (via intermediate certificates) signed by a trusted CA and if the hostname matches the certificate. If the last condition would not be enforced anybody with a valid certificate from a trusted CA could incorporate any other site.
To make use of fiddler and not run into this problem you should configure your browser to use fiddler as a web proxy and then use the real URL inside the browser instead of ip:port of fiddler.

Is it possible to automatically select correct client side certificate?

I have configured an Apache httpd website with SSL client side certificates so that only users who have installed the correct certificate in their web browsers can access the website.
If there is only one client side certificate installed the web browser will automatically select it (it is not the default, but it can be configured somewhere in the settings dialog). But if a user has more than one certificate installed, the web browser presents a list of certificates and the user has to pick the right one to continue.
The question is: Is there a way to configure httpd to send a hint so that the web browser can automatically select the required certificate?
The SSL (TLS) protocol only allows the server to specify two constraints on the client certificate:
The type of certificate (RSA, DSA, etc.)
The trusted certificate authorities (CAs) that signed the client certificate
You can use "openssl s_client" to see which CAs your Apache server trusts for client certs. I do not know how to configure Apache to change that list (sorry), but I bet there is a way. So if you can limit the list to (say) your own organization's CA alone, then you will have done all you can to allow a Web browser to select the client cert automatically.
As Eugene said, whether the browser actually does so is up to the particular browser.
I'd say that as selection of the certificate is a client-side task, there's no definite way to force the client use this or that certificate from the server side.
In addition to what #Nemo and #Eugene said, by default, Apache Httpd will send the list of CAs it gets from its SSLCACertificateFile or SSLCACertificatePath configuration directives.
However, you can force it to send a different list in certificate_authorities using the SSLCADNRequestFile or SSLCADNRequestPath directives and pointing them to another set of certificates. Only the Subject DN of these certificates is used (and send in the list). If you want to force certain names, you can even self-sign these certificates with whichever name you want. I've tried this (in conjunction with SSLVerifyClient optional_no_ca, and you can get clients to send certificates for CA certificates that the server doesn't actually have. (This isn't necessarily useful, but it works.)