secure email to users using gmail, hotmail, yahoo etc - c#

I need to send a secure email to my web site users who are using services like hotmail, gmail, yahoo etc. I am reading about sending secure email via PGP but I am confused it this can be done with users who are using these public email systems ( and not enterprise email systems).
Can someone please elaborate what exactly is the workflow for setting up a secure email? My understading is that we will have to have PKI infra-strcuture on our end and the users will have to install certificates on their machines. Is this correct?
Can these certificates be used with email services like hotmail, gmail etc?

I don't believe there's a way that you can have integrated end to end encryption in most consumer webmail services; I've never seen a provision for public and private keys in any one I've used and my gut feeling is that the computational overhead for doing encryption doesn't make sense to be running on the server. I'd be happy to be corrected on this point, however.
One solution might be to send them a plaintext email asking them to sign into your website to receive the information (provided your website connection is SSL-encrypted). This way, a potential email interceptor only sees that the target has received an email with a link to your website informing them that a message is waiting for them but not explaining the content of the message.
If you're absolutely sure that you want to send them encrypted email using PGP, you could try encrypting the mail on the server with the user's public key and sending it to them and expecting them to decrypt it themselves. However, for that to work you'd have to potentially generate a public/private key pair for the user and inform them of what "their" private key is, which defeats the purpose. In that case, a PKI setup is not the best idea, and a different shared-secret encryption method could be used instead.
Signing your email message automatically is not difficult, but automated signature verification would again rely on the webmail service providing it. Chances are that the users would have to verify the email signature against your published public key.

A perfectly good solution used by a lot of companies is to email the users a link to a secured web server which will then provide the content.
This requires a small element of initial set up for authentication, however it can be used for communication with anyone who can access the Internet via a browser.

Related

C# WebClient Encryption - Charles

is it possible to connect to SSL via a web client so that it can not be decrypted later by programs like Charles or Fiddler?
My Problem is, I have a Application white a Login, if the Password and Username from a User is correct, the Server returns Success. But if the user reads the response, he can easily fake it white Charles and „bypass“ my Login.
That depends on what you are trying to do, and why. Fiddler decrypts traffic by installing a root certificate on your computer, and then uses that basically make a man in the middle attack. Or in other words, with the users permission it subverts the security model of windows. So if you rely on windows to validate the SSL certificate used, there is nothing you can do about it.
If you only have one server that you really want toconnect to, you can validate that the certificate you are getting is the one and only one that you do indeed trust. This is known as certificate pinning.
If you are worried about someone storing the traffic and later using Fiddler to decrypt it, you can stop worrying.

Password is in clear text after imlementing SSL [duplicate]

I asked a question here a while back on how to hide my http request calls and make them more secure in my application. I did not want people to use fiddler 2 to see the call and set up an auto responder. Everyone told me to go SSL and calls will be hidden and information kept safe.
I bought and installed an SSL Certificate and got everything set up. I booted up fiddler 2 and ran a test application that connect to an https web service as well as connected to an https php script.
Fiddler 2 was able to not only detect both requests, but decrypt them as well! I was able to see all information going back and fourth, which brings me to my question.
What is the point of having SSL if it made zero difference to security. With or without SSL I can see all information going back and fourth and STILL set up an auto responder.
Is there something in .NET I am missing to better hide my calls going over SSL?
EDIT
I am adding a new part to this question due to some of the responses I have received. What if an app connects to a web service to login. The app sends the web service a username and a password. The web service then sends data back to the app saying good login data or bad. Even if going over SSL the person using fiddler 2 could just set up an auto responder and the application is then "cracked". I understand how it could be useful to see the data in debugging, but my question is what exactly should one do to make sure the SSL is connecting to the one it was requesting. Basically saying there cannot be a middle man.
This is covered here: http://www.fiddlerbook.com/fiddler/help/httpsdecryption.asp
Fiddler2 relies on a "man-in-the-middle" approach to HTTPS interception. To your web browser, Fiddler2 claims to be the secure web server, and to the web server, Fiddler2 mimics the web browser. In order to pretend to be the web server, Fiddler2 dynamically generates a HTTPS certificate.
Essentially, you manually trust whatever certificate Fiddler provides, the same will be true if you manually accept certificate from random person that does not match domain name.
EDIT:
There are ways to prevent Fiddler/man-in-the-middle attack - i.e. in custom application, using SSL, one can require particular certificates to be used for communication. In case of browsers, they have UI to notify user of certificate mismatch, but eventually allow such communication.
As a publicly available sample for explicit certificates, you can try to use Azure services (i.e. with PowerShell tools for Azure) and sniff traffic with Fiddler. It fails due to explicit cert requirement.
You could set up your web-service to require a Client-side certification for SSL authentication, as well as the server side. This way Fiddler wouldn't be able to connect to your service. Only your application, which has the required certificate would be able to connect.
Of course, then you have the problem of how to protect the certificate within the app, but you've got that problem now with your username & password, anyway. Someone who really wants to crack your app could have a go with Reflector, or even do a memory search for the private key associated with the client-side cert.
There's no real way to make this 100% bullet proof. It's the same problem the movie industry has with securing DVD content. If you've got software capable of decrypting the DVD and playing back the content, then someone can do a memory dump while that software is in action and find the decryption key.
The point of SSL/TLS in general is so that the occasional eavesdropper with Wireshark isn't able to see your payloads. Fiddler/Burp means that you interacted with the system. Yes, it is a very simple interaction, but it does require (one) of the systems to be compromised.
If you want to enhance the security by rendering these MITM programs useless at such a basic level, you would require client certificate authentication (2-way SSL) and pin both the server and client certificates (e.g. require that only the particular certificate is valid for the comms). You would also encrypt the payloads transferred on the wire with the public keys of each party, and ensure that the private keys only reside on the systems they belong to. This way even if one party (Bob) is compromised the attacker can only see what is sent to Bob, and not what Bob sent to Alice.
You would then take the encrypted payloads and sign the data with a verifiable certificate to ensure the data has not been tampered with (there is a lot of debate on whether to encrypt first or sign first, btw).
On top of that, you can hash the signature using several passes of something like sha2 to ensure the signature is 'as-sent' (although this is largely an obscure step).
This would get you about as far in the security way as achievable reasonably when you do not control (one) of the communicating systems.
As others mentioned, if an attacker controls the system, they control the RAM and can modify all method calls in memory.

Can I avoid storing MS Exchange credentials while still being able to authenticate (against EWS)?

I'm building an application that syncs data between users' Exchange Server accounts (version 2007-2013 supported) and the application.
The application can't use impersonation (at least not in the typical case) as users could be on any number of domains and exchange servers.
I know I'm going to have to ask for their username/email-address and password initially. However, I really don't want to be responsible for storing these credentials if I don't have to (even if they are encrypted, I'd rather not).
I'm not sure what questions to ask, so I'm going with these:
How does Exchange Server authenticate? Do the user's credentials get sent directly to the server as they are, or are the hashed together before being sent across the wire? If they are hashed, how can I get/generate this hash for re-use on successive authentications?
Does Exchange Server send some sort of authentication token that can be re-used later (and forever, until password change or invalidation)?
If you know of a solution to the problem, that the answers to these questions won't address, please do provide it instead.
Active directory federation services is exactly for such tasks. You can read about it there.
As mentioned by Kirill, ADFS 2.0 is one of the best solution for your task. You can also look into other SSO implementations as well. Though the main goal of SSO implementation is to maintain single Login state for multiple application (thereby reducing multiple Login prompt for each application), some of your application goals seems relevant. Please do a thorough research on all the tradeoffs before heading to the sso implementation since there is a small degree of complexity involved during implementation. SSO suits best if you are considering integration of multiple application in the future with the exchange server.
To answer some of your questions (in the same order - considering an SSO scenario with ADFS 2.0):
The authentication to exchange server will be done via ADFS 2.0 (Which provides security tokens (STS service) - to your application after authenticating with AD/ main Directory service). All the communication is encrypted and token signing certificates are used for Integrity and confidentiality.
The lifetime of Security tokens sent by ADFS 2.0 can be configured and reused as required. Please see this blog post for more details.
Also you can configure the ADFS 2.0 (Federation Service) to send only the relevant claim values (like username and email address) to the application, thereby improving the data security.
The System.Net.CredentialCache should work to suite your needs. The WebCredentials is a wrapper for the System.Net.NetworkCredential. Depending on the connection type/domain ect you should be able to utilize System.Net.CredentialCache.DefaultNetworkCredentials or System.Net.CredentialCache.DefaultCredentials
perhaps you should take a look at this Links Connecting to EWS by using the EWS Managed API , Connect to Exchange - Getting Started Tutorial? hopfully it will give you a new idea how to solve your problem :)
because if i understand the information correctly you maybe over think problem but i haven't any experiences so i could also absolute wrong
Bottom Line
If you can't configure anything on the server, there's no automatically generated token to use. It's unfortunate, but you're facing the same general problem that web browsers have--saving the password.
It's worth noting that any authentication needs to be over SSL (an https connection) to prevent a third party listening in on the authentication.
Password storage thoughts:
My suggestion is then to be somewhat creative when storing the password. You can use a keyed encryption algorithm, and then use a hash to generate the key, letting you arbitrarily choose what goes into the key. You would want at least 3 pieces of information going into this: something unique to the device, something unique to the app, and something unique to the exchange server.
For example:
a unique id given by the device (it doesn't matter whether or not this value is app-specific or not, merely that it is consistent)
a (long) string of information compiled into the app, possibly keyed to installation specific values, say the time when the app was first used
something unique to the destination, like the DNS name and perhaps some more specific server info
If you're willing to provide the option to the user, you could have an authorization PIN of some kind that would also be added to the data.
All this data gets put together in one byte array and hashed. The hash (or part of it, or it twice, depending on the hash size vs. the key length) is then used as the key for the encryption of the password.
You could also include some check information along with the password to be able to check client side whether or not the password was decrypted correctly. (If the wrong data is hashed, the wrong key is generated, and the wrong result comes from the decryption).
It's worth noting that all the information to be used for putting into the hash needs to be stored on the device, which is why I would suggest a Pin to authorize the usage of the account.

WCF Authentication / WCF REST Authetication..Different Method?

I have made a WCF REST service which consumes data from an OLAP database and it is not Microsoft technology, ultimately, I would like to connect many other OLAP database to a single platform.
And after a lot of reading, the security for WCF REST is very discouraging, in summary, I have 2 choices, one is to use the Basic Authentication which expose username and password over the wire, or maybe a bit better, using Basic Authentication with SSL, now I need to get different certificates from the webserver. Or using Digest Authentication, which use an encrypted password and authenticate against the database, that's the best option, but in my case, it is not possible as I am not using Microsoft technology, the security is on different platform and I cannot encrypt my password using MD5 because the database cannot read the encrypted password.
That concludes me only be able to use Basic Authentication with SSL, but is this the correct way of doing? I see many products out there doing something similar to what I do, when they login, I do not see https, but only http, are they not secure and easy to hack?
I am not trying to make a bullet proof website, but a simple website, using Basic Authentication is too simple, or in fact it's almost like giving away the password, but using https, is that overkill?
So, after REST being that discouraging, let's not use REST, use the normal WCF, from what I have read, they shares the same problem.
Please give me some guidance. I think I have lost.
Many Thanks
PlayKid
Often, basic authentication is used for regular websites and yes, the username and password often go over the line readable if used with http. Https is already better, because the information is send encrypted over the line. But in practice, you only see this in place for commercial or banking applications. You cannot use MD5, which is a pitty, because that would be sort of middle-of-the-road approach.
So, depending on the application you will expose, use http for simplicity or https with a bit more complexity and safety.
By the way, big safety problems often have to do with SQL injection or a hacker being able to get some admin level privileges on your site. That way they get acess to a lot of info, while sniffing your line and getting a single user password combination is relatively harmless, if you take the needed precautions and counter measures.
Basically, Basic authentication with SSL is really very secure and shoul be used if its going to be exposed to outside world.
One easiest hack approach I have seen before and if you just want to authenticate (not authorize a endpoint) clients which are known set of clients use:
OperationContext.Current.ServiceSecurityContext.WindowsIdentity.Name
This will provide username accessing the service, Authenticate this usern with your DB or AD using LDAP if a valid user is accessing the service and with every request add a encrypted key that user needs to send as part of request. This way you know the username and encrypted key from the request.
You can also use this along with Basic authentication to be sure its not insecure.

How to implement Client Authentication with ServiceStack.Net

I am developing web services using the servicestack.net library.
In my scenario, the web services will be called from a WPF application. I need the ability to authenticate that only an approved client app is calling my service.
Is this as simple as hardcoding a "username" and "password" in the client application? This certainly does not seem like the proper approach. Is there a better way?
EDIT
In addition, on the client end, Users themselves will be able to login with a username/password and initiate requests to the service(not sure if this effects anything, so I thought I would mention it),
For more background information about Authentication in ServiceStack see this question.
Normally you would authenticate users not clients which you seem to be doing in addition. But if you're trying to lock down services so their only accessible via a specific set of clients you should look into employing some PKI into your client and server.
Basically something along the lines of: the client sends an additional token at login with an encrypted version of the user:password together with a private key embedded in the app. The server has the client public key and so would do un extra validation step on Login to unencrypt the user:pass token and compare it with the validated user credentials.
If a PKI solution is too heavy, an alternate strategy without using encryption could be for clients to ship with a secret Guid which when they login which will send an MD5 hash version of the Guid and the current time, as well as the unhashed version of the time. If the time is within a specified threshold and the MD5 hash is valid then their using an authenticated client.

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