Understanding SSL Certificate Types - security

I'm building my first web app and I have two questions about security.
I'll send and receive very sensitive data with POST request to my
api which will be hosted on Azure or AWS. Can I send and receive
data in plaintext over SSL, is it secure? I can access my
azure web site over https, is it secure enough or should I buy another
SSL sertificate?
I've searched a little bit and there are different types of SSL
certificates, I read some certificates provide green padlock or green address bar but I don't need these kinds of things since my web app only
will be available to my mobile app and there will be no content to browse. Only one page with download links to my mobile app in case someone finds this site. So all certificates are secure on same level for my situation?
P.S. I won't add custom domain name, if that's relevant.

Answering your questions one at a time;
Modern implementations of SSL are generally considered to be pretty
rock-solid; its used by banks, healthcare institutions, and major
internet companies. Sending data in plaintext, over SSL, is
safe enough for those applications, and trying to replace SSL with
your own encryption scheme is almost certainly more trouble than its worth.
You should probably get your own SSL certificate; I don't know what restrictions Azure has on https access, if any, and its always bad practice to rely on a key you cannot control.
SSL relies on networks of trust; browsers (and other internet applications) validate the certificates sites send them against a
set of trusted authorities. If the certificate has been approved
(signed with the authority's private key), the browser accepts the
certificate as genuine and uses it to negotiate an SSL connection
with the site without further complaint. This is what that green
padlock/address bar means; that a site has provided a valid
certificate signed by an authority the browser trusts. This doesn't
mean that a signed certificate is inherently more secure than an
unsigned certificate, however. Both use the same cryptographic
algorithms, and (can) have the same length keys, and the SSL
connections each can set up are equally secure. The difference
between the two is that you can't verify the "authenticity" of an
unsigned/self-signed certificate; an attacker could intercept the
connection and replace an unsigned certificate with their own
certificate, and the browser would have no way of telling if it got
the right certificate or not. You can overcome this problem in your
application, however, with a technique called "certificate
pinning".
Essentially, you package the public key for your certificate with
your application, and your application only accepts the certificate
associated with that key when setting up a connection.
Ultimately, it depends on your attacker model. Are you protecting this data from criminals and casual wiretappers? Or are you trying to hide it from government surveillance and intelligence agencies? For the former, an SSL certificate signed and issued by a reputable authority is more than sufficient. For the latter, you have to consider where your certificate is coming from, and who can access the root CA that issued it; it might be better to generate your own, and devise some further scheme on top of SSL.

Related

Secure frontend connecting to backend with self signed certificates

Our frontend at domain.com uses an API located at api.domain.com.
For domain.com, we use SSL by LetsEncrypt. For the backend, however, it is much simpler to use self signed certificates.
Will users be presented with Red Warning Banner if they go to domain.com, which connects to https://api.domain.com with self signed certificates? Is this okay practice? Furthermore, can we replace https://api.domain.com with external IP instead?
That's not a good idea in general. The purpose of a certificate is to allow a client to verify that it is actually talking to the right server, and not for example to a man-in-the-middle attacker. The way it does that (somewhat simplified) is the certificate includes the public key of the server, and the domain name ("common name") of the server the client intended to communicate with. The certificate is then signed by another certificate of about the same type and contents and so on, until the chain reaches a certificate that does not need to be signed by another, because it is already trusted by the client (it is in the trusted roots list of your OS for example).
A self-signed certificate doesn't have this chain of signatures, it is called self-signed, because the certificate used to sign it is itself. There is no way for a client to verify the certificate (unless it explicitly has it listed as trusted of course). This means an attacker can spoof (impersonate) your API by self-signing a different certificate for the same domain name, but with a different keypair. This might allow stealing credentials or serving fake data. Note that the attacker might also relay the information entered by the user (all the requests made) to the real API, so responses (also received by the attacker first, but relayed to the victim) can easily look very real without much background information.
This could (in theory) be solved by certificate pinning, but in case of a Javascript client that's going to be difficult (if at all possible). HPKP would seem like a solution, but HPKP won't work with a self-signed (not verifiable) certificate. I'm not sure if Javascript has an appropriate level of access to the server certificate to implement pinning.
Even if you did implement pinning, a self-signed certificate also cannot be revoked. Think about what would happen if you discovered a compromise of the TLS key used for https in your api domain. You would have no way to revoke the key, so clients would still accept a MitM attacker serving the compromised key.
There goes a lot of effort, and you could implement something that is not standard, hard to get right and error-prone.
Or you could just use a free letsencrypt certificate for api.domain.com as well, for which all the necessary infrastructure and setup is already done on the main domain. :)

What are some approaches to exchange data without using SSL/TLS

When creating any kind of application web,api etc; This days the best practices recommend to secure endpoints by using TLS, but what we can learn from the cloudbleed issue, is that it may not be enough.
Therefore I would like to know what could be done to keep a certain level of security even when TLS is compromised.
For web applications what I currently use is jsencrypt, basically encrypts all data on client browser side before it is sent, but in order to to this I need first to exchange a shared secret (token/cookie) between the server and client, but when dealing with API's that don't support javascript what could be used?
Regarding the exchange of tokens, by instinct it may be obvious to say use OAUTH, OpenID Connect, json tokens , but all of them require or delegate trust to TLS, and again when this is compromised it became useless.
If I am right OpenID could be used without SSL to share a "common secret" by doing Diffie–Hellman key exchange, is there something similar that could be implemented keeping in mind that if TLS gets compromised, easy measure could be taking like revoking tokens or changing "salts" ?
For now I think by following the gpg or rsa (private/public) keys is the way to go, in a way that probably everyone could have access to the public keys but will not be available to see the content of some data signed to a specific user.
But question remains in how to exchange that very first "known secret" between client and server avoiding a possible man in the middle attack considering TLS can't be trusted.
The problem of exchanging the first "known secret" is the same for all protocols, SSL or not. SSL is a public key infrastructure where the basic information that needs to be distributed is the public key of the root certificate of the certificate issuer. The public keys for all ssl certificate issuers are distributed with the browser installation.
Any protocol will depend on some information that is communicated between the server and client in a different channel from the channel where the communication is established. If you don't trust the SSL infrastructure, you will have to send this information by email, postal mail, sms, or by some other means.
However, your problem does not start with the keys neccesary for the encryption libraries you are using in you web application. Your very web application (the javascript files) are also sent from the server to the web browser over SSL. If your SSL communication is compromised by a man-in-the-middle, this man-in-the-middle is also probably able to change the web pages and javascript code that you send to the browser. He could just rewrite your application and remove all encryption code, add new fields and messages for the user, send the user to a different site and so on.
The SSL infrastructure is really a cornerstone in web security, and a neccessity for web applications. Without it, you would have to build a custom protocol for sending encrypted web pages and write a custom browser that would understand this protocol.
With all that said, it is of course possible to add a tiny layer of extra security on top of SSL. You may i.e. create a private/public keypair for each user, send a public key to the user and encrypt all messages from your server to the user with the private key. This could protect against a scenario where a main-in-the-middle is able to listen to the communication but not able to change your messages.

Are certificates useful for intranet SSL?

I've been tasked with development of an intranet interface for command line software, and now I'm researching security options. Our command line application is finished, but I haven't started writing the web interface. I don't know exactly what the security requirements are for potential customers, although I believe ssh is generally acceptable for the command line interface. With this in mind, I'm asking for help developing a menu of choices with their associated pros/cons. Some day, we may consider releasing our web interface to the internet, so I'm willing to consider more security than currently necessary if it's easy and/or free.
I've been doing a lot of reading, and my tentative conclusion is that SSL security with no certificate is the best approach, not because less security is unacceptable, but because SSL is the standard and because it doesn't appear to be difficult to set up. I, a security non-expert, wouldn't need to explain why less security is acceptable to security non-experts. I could upgrade my application to use a certificate in the future if necessary.
Here's a list of SSL related security choices, sorted by my perception of security level with my comments. What level of protection do I need?
No SSL. This might be acceptable if our customers aren't worried about their employees seeing/changing each others' data. Their employees might want to share results with each other anyway, and I could use IP based access control and/or passwords for security.
Do SSL with no certificate. This encrypts the communication, which at least protects the data from being read by unauthorized employees. Using a password, this is the same level of security as ssh on the command line, right? I don't need to worry about man-in-the-middle attacks in an intranet, right? A con for this approach would be if there were loads of browser warning messages.
Do SSL with a self-signed certificate. What does this give me that no certificate gives me? If the DNS can be changed inappropriately, then the customer then my application is the least of their concerns. Worded another way, if the DNS can change, then I think ssh would be vulnerable too.
Do SSL with a local Certificate Authority. OpenSSL lets me make my own Certificate Authority. What does this give me that a self-signed certificate does not? I'm assuming that on a LAN, it's less important for the server to be verified.
Do SSL with an external Certificate Authority. Is there ever a reason to go this route for an intranet? I found some "intranet certificates" for sale online -- but it's not clear what they're offering I can't do myself.
For reference, this page might be useful for comparing certificates:
http://httpd.apache.org/docs/trunk/ssl/ssl_faq.html#aboutcerts
[update]
Here's an article discussing the risks and rules of obtaining an internal certificate from a public CA.
Yes, certificates are still useful for Intranet SSL.
There's an important difference between SSH and SSL-without-a-certificate: when you first connect to a server with SSH, your SSH stores the server's fingerprint. If you then try to connect to what the SSH client believes to be the same machine but gets back a different fingerprint, it alerts you that there might be someone intercepting your communications.
SSL-without-a-certificate, on the other hand, does not store the server's fingerprint. Your communications will still be encrypted, but if someone somehow hijacks the DNS server as you mentioned, or, as Rushyo notes, does ARP poisoning or something similar, they would be able to perform a man-in-the-middle attack. SSH, as previously mentioned, would (supposing you had connected to the correct server some time in the past) notice that the fingerprint had changed and alert you.
A self-signed certificate would be comparable in security to SSH. A man in the middle could generate their own self-signed certificate, but as long as your applications are configured to only accept that self-signed certificate, you should get an alert similar to that that SSH will give you.
A local certificate authority gives you security similar to self-signed certificates, but may be more scalable. Should you have multiple servers, each can have their own certificate, but a client only needs the top-level one to trust all of them. If a server is compromised, you can revoke its certificate rather than having to change every server's certificate.
I don't believe an external certificate authority has any advantages, other than possibly less configuration if your machines already have the certificate authority trusted.
Lastly, I don't know enough about two-factor authentication to evaluate it, but for most applications, SSL should be sufficient.
Disclaimer: I am not a security expert.
Do SSL with an external Certificate Authority. Is there ever a reason to go this route for an intranet? I found some "intranet certificates" for sale online -- but it's not clear what they're offering I can't do myself.
The benefit is that you don't need to learn how to setup your own Certificate Authority if you need to manage a decent number of certificates and/or machines. Such a certificate would already be trusted by all browsers without you needing to install your own certificates into the trusted store.
However, this is actually less secure because somebody could purchase a certificate for a different intranet and use it on your network. For this reason, SSL vendors no longer offer this service. For more information, see: https://www.godaddy.com/help/phasing-out-intranet-names-and-ip-addresses-in-ssls-6935
If you only have a very small intranet, then I would recommend using a self-signed certificate, and then just add each self-signed certificate to each computer's trusted store.
However, it quickly becomes impractical to install a new certificate on every computer in your intranet whenever you want to add a new computer. At this point, you want to setup your own Certificate Authority so that you only need to install a single CA certificate in each computer's trusted store.

Can I use a self-signed SSL certificate for commercial purposes?

I'm making a server-client to use ssl for sign up and login process.
(and this is for iphone if it matters)
I just started looking at what ssl is and how to use it, and
saw there is a certificate in the process which can be bought or self-signed.
If I use self-signed certificate in web server, web browser would alert that cert is self-signed, that I understand.
But what would happen if I use self-signed certificate in regular application with tcp(not http), specifically iphone.
I just want to make the signup/login
info(their password) to be secure,
and hoping that using self-signed
certificate would be ok for this
purpose. But I also need to make
sure this won't cause "not trusted
certificate - alert" type of
interruption when used in application
other than a web browser.
Edit
I understand that "not trusted certificate alert" is saying client shouldn't trust this server.
But in my situation, client doesn't need to authenticate with the server.
The server just needs to get client's password in a secure way.
To answer your question: You can, but you shouldn't!
First, using SSL only for authentication isn't secure at all. The authentication process probably produces some kind of session (e.g. cookie) which is then transfered without encryption. Therefore, the session can be stolen (see Session hijacking).
Second, using a self-signed certificate allows man-in-the-middle attacks. So, someone can steal the user's password and he probably won't even notice it. The user doesn't know the difference between the alert that pops up when the client receives your self-signed certificat and the pop up that shows when the attackers self-signed certificate is used.
My advice: Don't use self-signed certificates. When an attack happens it's bad for you and your customers.
When you use an SSL connection to encrypt a login dialogue with a password the server sends the client a public key (in the form of a certificate), and the client generates a one-off session key, encrypts it using the server's public key, and sends it to the server. The server can then decrypt the session key because it has the private key.
The user then encrypts his password using the session key and sends that to the server, which can decrypt it because it knows the session key.
Now, without PKI if an attacker wanted to learn your password he could spoof the server. He'd send you his public key and you'd generate a session key, etc., in the usual way and send him your password which he would be able to decrypt because you'd be using his key without knowing whether you can trust it.
PKI protects you against this kind of attack by requiring that public keys are distributed as certificates. If you trust the CA that signed the certificate you can tell that the public key really does belong to the server and that it's safe to use it to encrypt your password. If you don't use a certificate -- or if you use an untrusted certificate -- you generally have no idea who you are sending your password to.
You don't give enough information about your own particular use case to say for certain whether you can use a self-signed certificate ... For example: It may be that you have one fixed certificate that is distributed in advance by some trusted channel and that you can check that the correct certificate is being used when you begin your SSL conversation. If that's the case then your client already knows that it has the correct public key and doesn't need to be able to check a signature. In general, though, you need a proper certificate signed by a trusted CA or else you have no security.
That's the entire point of trusted signing authorities - anything signed by someone else is supposed to give a security alert. So, no, there's no useful way to override this (unless you have control over the client computers - e.g. a self-signed certificate used for company-internal sites, when you can add your own CA into the clients' list), either for web browsers or anything else.
With a self-signed certificate, how can a user know whether the certificate is yours or an attacker's? He can't.
If you completely control both ends of the process (server and client), you can of course instruct the client to always trust "certificate from Eugene with a fingerprint of A01AABB546AC", for example, but then you need to build your own certificate infrastructure (expiration/revocation).
You will add no theoretical security by using a self-signed certificate, because of the possibility of man in the middle. The counterparts (your client and your server) in this communication will have no additional information about who is talking or listening, whereas the point of this kind of encryption is to make sure that there are only two participants in the communication and that the identity of at least one of them is known.
In your case, the password will not be transferred to you securely, because you don't know if it has passed through a third party on the way. Likewise, the user won't know who he sends the password to.
In practice, a man in the middle attack will be a bit of work to set up, and maybe that obstacle is some kind of security, but contrast that to the annoyance of forcing your users to accept a security warning with unclear consequences, and indeed the risk of "false sense of security".
There are companies that offer free certificates with the lowest form of validation (they will only check that you "own" the e-mail address hostmaster#domain). That way you won't have to do with the warning, either.
Unless there is a way for you to package your certificate or its fingerprint with the app, as Piskvor said.
Moved to answer - for this type of thing you should be fine. The only thing the users won't get is a way to confirm the trust level of the cert (like you could do with a signed cert in a browser for example) but as per your comment to #Piskvor that doesn't sound like an issue: you aren't using it for that.

How does SSL actually work?

Whenever I see it being talked about, it sounds like one simply 'turns on' SSL and then all requests/responses to/from an online server are magically secure.
Is that right? Is SSL just about code - can I write two apps and make them communicate via SSL, or do you have to somehow register/certificate them externally?
Secure web pages are requested on port 443 instead of the normal port 80. The SSL protocol (plenty complicated in and of itself) is responsible for securing communication, and using the certificate information on both the SERVER and the BROWSER to authenticate the server as being who they say they are.
Generating an SSL certificate is easy. Generating one that is based on the information embedded in 99% of web browsers costs money. But the technical aspects are not different.
You see, there are organizations (Verisign, Globalsign, etc...) that have had their certificate authority information INCLUDED with browsers for many years. That way, when you visit a site that has a certificate that they produced (signed), your browser says:
"well, if Verisign trusts XYZ.com, and I trust Verisign, then I trust XYZ.com"
The process is easy:
Go to a competent SSL vendor, such as GlobalSign. Create a KEY and Certificate Request on the webserver. Use them (and your credit card) to buy a certificate. Install it on the server. Point the web-browser to HTTPS (port 443). The rest is done for you.
SSL is a protocol for encrypted communications over a TCP connection (or some other reliable scheme). The encryption uses public key encryption using X.509 certificates. SSL handles both privacy and trust. These are related: if you don't trust the server, you don't believe that the server hasn't handed out its private key to everyone in North America.
Thus, the client has to trust the server's certificate. For public sites, this is arranged via a hierarchy of certificate authorities, with the root authorities trusted, automatically, by browsers and things like the JRE's socket implementation.
Anyone can generate a self-signed certificate for a server, but then the client has to be manually configured to trust it.
SSL is not, in itself, a magic bullet that makes everything secure. Security has no such things.
SSL is, however, an already-designed, ready-to-use system for solving a common problem: secure stream communication over a network connection.
There are two things you need to do to secure your application with SSL:
Modify the application's code to use SSL.
Determine the certificate trust model (and deploy and configure the application respectively).
Other answers and documentation provide better answers to how to do each of these things than I could provide.
I'll throw caution to the wind and attempt to condense an enormous subject.
SSL attempts to solve two problems:
1) Authentication and hence trust i.e can the client trust the server and vice versa
2) Communication without eavesdropping
1) Is handled by means of an intermediary i.e a trusted 3rd party - these are called 'Root Certificate Authorities' ( or Root CAs ) examples include Verisign, RSA etc
If a company wants to authenticate users and more importantly if a user wants to authenticate the company's website it's connecting to i.e your bank then the Root CA issues the company a certificate which effectively says 'I the trusted Root CA verify that I trust that Company X are who they say they are and am issuing a certificate accordingly'. So you get a chain of trust i.e I trust the certificate from ACME Co because Root CA Verisign created and issued it.
2) Once the two parties have authenticated then the certificate ( typically X590 ) is used to form a secure connection using public/private key encryption.
Hopelessly simple and incomplete but hope that gives a rough idea
Yes and no. You should self-sign a certificate and test the site with SSL internally before deploying it with SSL, first of all. To make the public site secure under SSL, you will need to purchase a certificate from one of any number of certificate providers. Then you will have a certificate signed by a trusted third party, tied to your domain name, so that users' browsers won't complain that the certificate is invalid, etc. Turning SSL on is pretty much just flipping a switch, otherwise.
For the most part you need to buy and register a certificate externally.
You need to have your server certificate signed by a Certificate Authority (CA), for which they will charge you. The client needs to trust that CA and have a copy of the relevant CA public key. The client can then check that you are who you claim to be (including domain name (from DNS) and display name for https).
This is a good tutorial on how to create self signed certificates for Apache.
If you want to know how SSL works on either the Server or the Client, then I suggest Googling it. As you suspected, it is a ridiculesly complex procedure, with lots of communication between the client and server, a lot of very peculiar math, and tons of processing. There is also a lot of theory involved, several protocols and many different algorithms and encryption standards. It's quite incredible how changing http:// to https:// is so simple to the user, but results in so much work for both sides, and is so secure. To really understand it you need to take a security course (multiple courses to fully understand it), as the entire history of encryption goes into making your login to Gmail secure.
Turning on TLS (colloquially "SSL") does not make your site magically secure. You may still be vulnerable to application-level vulnerabilities like stack overflows, SQL injection, XSS, and CSRF.
As other answers have explained, TLS only protects against a man in the middle. Traffic between a client and a properly-configured TLS server cannot be intercepted or modified, and the client can reliably confirm the identity of the server by validating the X.509 certificate. This prevents an attacker from impersonating your TLS server.
SSL actually does two things:
Encrypts the communication so that an observer seeing the data stream will not be able to read the conversation.
Guarantees that you are talking to who you think you are talking to.
It is only for #2 that you need to get official certificates. If you only care to encrypt the communication without setting up a trust relationship, you can use self-signed certificates or you can use an algorithm that does not require certificates (i.e. Diffie-Hellman).

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