How to enforce TLS on Gmail (Gsuite Basic) - ssl

I want to strictly enforce TLS on all inbound/outbound emails from gmail (gsuite basic) for a particular organization/domain. I did read this article:
https://support.google.com/a/answer/2520500?hl=en
It asks to create an address list to setup inbound/outbound rule to enforce TLS. However I want to have TLS enforced irrespective of address and want to enable following behavior:
Outgoing mail: Mail won't be delivered and will bounce. You'll get a non-delivery report (NDR). Only one send attempt is made (no tries again).
Incoming mail: Mail is rejected without any notification to you, although the sender will receive an NDR.
Any suggestions on how this can be accomplished?

You can’t do that, in fact based in this article at point 6.:
https://support.google.com/a/answer/2520500?hl=en
“You must create a domain or address list to enforce TLS compliance for any inbound or outbound messages”
Gmail by default will use TLS, however, if the destination domain can’t establish TLS connection, Gmail will do an insecure connection. However, nowadays all domains are all by default establishing TLS connection and transmitting data over it. It’s rare you will find a domain that doesn’t support TLS connection.
Therefore, first of all, you should know which domains you usually contact that doesn't support TLS connection, and listed in the TLS compliance rules.
The idea of this policy is not making a long list of domains but only a few that customers already know that they don’t support TLS connection hence list them on the TLS.
There is a feature for a higher message encryption but is available for G Suite Enterprise edition: https://support.google.com/a/answer/6374496?hl=en
In fact what it may be a workaround is to Send and receive your email first to an external server that allows you to achieve this.
If this is the case you should Set up:
Set up an inbound mail gateway: https://support.google.com/a/answer/60730?hl=en
Set up an outbound mail gateway: https://support.google.com/a/answer/178333?hl=en
An consider a third party tool as : https://zix.com/products/email-encryption

Related

is there any security issue that can be expected when the mqtt client doesn't provide public key certificate during TLS handshake?

I am building up a small iot-like system, where mqtt devices(clients) are sending and receiving security-related critical information or commands.
I have got to know that TLS connection can be built optionally without client authentication thru PK certificate on the client side.
Normally, mqtt client devices don't have enough resources to support PKI, where at first it has to store a certificate and from time to time, to update it with newly issued ones when validity has passed or when the original certificate has been revoked.
That was, I think, why many of mqtt brokers have an option to configure on/off the client authentication during TLS handshake.
However, my concern is if there would be any security issue from passing the client authentication step, like, for example, a chance that some other malicious devices impersonating one of my devices can connect to the broker could obtain those critical information and commands.
My question is what best options and practices I can take to minimize that kind of risk considering the constraint resource of devices.
Missing client authentication means that everybody including an attacker can claim to be a valid client. There can be use cases like public services where this is not a problem and there are other use cases where the server wants to restrict access to specific known clients only.
There is no definitive answer to this question, it will always depend on the following factors, and only you as the designer can answer them:
What is the threat model you are working with? E.g. Who are you trying to keep out of the system and why, what are the consequences of somebody connecting a rouge client?
How much are you prepared to spend? If you intend to deploy client certificate or even a unique username/password for each device, how will it be protected? Does the hardware you intend to use support a secure enclave/hardware secret store? Meaning how hard would it be for an attacker to extract the client username/password or secret key from the device?
What other security measures do you have in place? Do you have Access Control Lists to protect which topics a client can publish/subscribe to? Do you have monitoring in place to detect malicious actions from clients so they can be disconnected and banned?

I am so confused about Transport level security in WCF vs SSL on Internet

I have read a lot of articles saying that in WCF you have two types of security one is transport level and other is message level. Transport level security must be used when you have intranet connection as it provides point to point security and underlying protocol should be SSL....
But if I search on how to secure public websites they all say use HTTPS(SSL) again SSL.
These two statements are contradictory.
Questions:
What exactly is the meaning of point to point security here?
If SSL is only point to point(and not end to end) then why people use it for public websites?
HTTPS encrypts data from point-to-point, and once the data reaches one of the points and is decrypted, no security guarantee is made from that point onwards. Intermediary nodes, however, cannot read the information.
Message security, on the other hand, can encrypt data to be decrypted only by a certain recipient, which can be a separate entity from the receiving end. The receiving end might eventually forward the encrypted message to the intended recipient who will be able to decrypt the message.
An analogy would be email. If you establish a connection with your mail server using transport security (e.g. HTTPS), any information is guaranteed to be secured from your machine to the mail server. However, anyone with access to the mail server (e.g. server administrators) will be able to read the content of the email.
On the other hand, if you use message security to encrypt the message so only a specified recipient can decrypt it, the actual email message is encrypted (and not simply the communication between you and the server), so that even once the message is received by the server, it is still encrypted. Only when the email server forwards your message to your intended recipient, the recipient can decrypt the message using his own private key, thereby keeping the email private across a whole path of delivery while not requiring direct communication by the sender and that recipient, as is required by transport-level security.
Of course, some parts of the message must remain visible to the email server, for example the recipients address, and so you may want to use both levels of security: message security will ensure the mail server (or any party except the recipient) can't read the content of your email, and transport security will additionally ensure that a third party listening in to the communications between you and your mail server can't find out who you're sending an email to (unless the mail server divulges that information to that third party
Taken from WCF Transport security weakness
Read more here https://msdn.microsoft.com/en-us/library/hh273109(v=vs.100).aspx
Answer to question 2 :
Because once it reached to the IIS Server which is hosted by the company itself/or in Data center which has all firewalls and other security measures which is hard to bypass which means no one can read your message from that server unless is can hack everywhere it saves oecerhead of tcp security.

WCF Service with Message Level Encryption over HTTPS

I have seen one or two questions about this but no definite answers. I have a customer requirement to implement a WCF-based client/server solution using Message Encryption AND HTTPS. I understand that WCF doesn't support this as standard, and the options are HTTP with Message Encryption, HTTPS without Message Encryption, or HTTPS with Message Credentials.
None of these will satisfy the customer requirement. I have control over both the service and the desktop-based clients. The service is hosted at my location and the clients access it over the internet.
I have dug around for days (and nights :( ) trying out custom bindings and so on, but whenever I try to combine message encryption with Https, I come up against this error:
"The binding contains both a SymmetricSecurityBindingElement and a secure transport binding element. Policy export for such a binding is not supported."
I would prefer to user username/password for authentication but I am prepared to use client certificates if this makes it possible. So far I haven't found any combination which is acceptable to WCF.
Is there any way to achieve this or am I just wasting my time? I would value a quick answer because my customer's deadline is drawing very near!
Thanks!
According to this, the special both mode for security (meaning both message and transport) is only supported in the NetMsmqBinding binding, which I'm guessing, is not an option for you. Does your client happen to be the NSA? (Just wondering why anyone would need their communication encrypted twice).
OK I've found a solution ...
Using IMessageInspector I intercepted the incoming and outgoing messages so that they can be encrypted and decrypted. Encryption uses a symmetric technique - best because asymmetric only allows encryption of short strings and is very slow.
The downside is that both ends need to have the private key of the certificate - so the cert needs to be installed on both client and server machines (or the key could be placed in config). This works for me though because the number of users is limited and all are under the control of the IT dept.
If I had more time I would have looked at setting up a second SSL connection with a different cert, purely to handle the certificate negotiation and avoid placing the cert on the client machine. Using SslStream was a possibility but I wasn't sure whether I could access key information to use for my own encryption, or whether this is held privately within SslStream class.
For now I'm just pleased to have it working before my deadline (only just though :) ) ...

WCF transport security and https

I'm trying to understand more why I shouldn't use WCF transport security over the internet. From the answer here I'm told the chain of hops may not be secure. But isn't transport security just like https (which is widely used on the internet)? Or maybe I should ask, what is the difference between wcf transport and https?
If I need to explain myself clearer, please comment.
Thanks
Transport security is indeed very similar to HTTPS (and identical in many cases). What it provides you is an encrypted tunnel between your client and the server. Providing there's a direct connection from your client to your server, it's perfectly fine (providing that your client verifies that it got the right server certificate). If your client is talking to another intermediate server, on which you rely to pass the message to your server - then that intermediate server would get unencrypted data.
An example :
You have a company that processes payments. Because of some regulations, you need servers in each country, and those in turn pass the requests to your main server in the US.
You want to make sure that even if the local hosting company tries to find out what details are being passed, they can't.
That is what Message Security provides you - you trust only the client and your main servers, so you want only them to be able to encrypt and decrypt.
With Transport Security, there would be two transitions - the client will encrypt, and the intermediate server will decrypt. Then it will encrypt again, and your main servers will decrypt. As you can see, there is an intermediate phase where the data is plain in RAM in the intermediate server.
This MSDN article describes it very well, and where to use each :
MSDN
Look at another answer on the link you gave. It explains that the case where transport security not sufficient is when the client doesn't check server certificate. I quoted the answer below:
Yes it is 100% secure when the clients (which most clients do) validate the server certificate.
The multiple hop scenario mentioned here is complete bogus. This is only true when the same message travels through various applications. Like for example several application brokers. If these brokers do not communicate securely then the message can be read by intermediate network sniffers.
In other words, client/server communication over the internet is 100% secure even when there are a million routers in between but it is only secure when the client validates the server certificate as the client could connect to a man-in-the-middle host that could impersonate the server with a false certificate. If the client does not validate the certificate the message could be compromised.
I'm trying to understand more why I shouldn't use WCF transport security over the internet
You should not because (Quoting from here).
Transport Security
Transport security is used to provide point-to-point security between the two endpoints (service and client). If there are intermediary systems between client and the service, each intermediate point must forward the message over a new SSL connection.
Message Security
When using message security, the user credentials and claims are encapsulated in every message using the WS-Security specification to secure messages. This option gives the most flexibility from an authentication perspective. You can use any type of security credentials you want, largely independent of transport, as long as both the client and service agree.

WCF Transport security weakness

On 2nd edition of "Programming WCF Services" By Lowy, ch 10, page 512.
Lowy said about Transport security: Its main downside is that it can only guarantee transfer security point-point, meaning when the client connects directly to the service. Having multiple intermediaries between the client and the service renders Transport security questionable, as those intermediaries may not be secure. Consequently, Transport security is typically used only by intranet applications.
HTTPS is one of Transport security options, How previous paragraph applies to HTTPS ?!!, HTTPS encrypts every thing all the way from start to end points. Also every e-commerce application in the world is using HTTPS, how you can limit it to intranet applications!!
Thanks
HTTPS encrypts data from point-to-point, and once the data reaches one of the points and is decrypted, no security guarantee is made from that point onwards. Intermediary nodes, however, cannot read the information.
Message security, on the other hand, can encrypt data to be decrypted only by a certain recipient, which can be a separate entity from the receiving end. The receiving end might eventually forward the encrypted message to the intended recipient who will be able to decrypt the message.
An analogy would be email. If you establish a connection with your mail server using transport security (e.g. HTTPS), any information is guaranteed to be secured from your machine to the mail server. However, anyone with access to the mail server (e.g. server administrators) will be able to read the content of the email.
On the other hand, if you use message security to encrypt the message so only a specified recipient can decrypt it, the actual email message is encrypted (and not simply the communication between you and the server), so that even once the message is received by the server, it is still encrypted. Only when the email server forwards your message to your intended recipient, the recipient can decrypt the message using his own private key, thereby keeping the email private across a whole path of delivery while not requiring direct communication by the sender and that recipient, as is required by transport-level security.
Of course, some parts of the message must remain visible to the email server, for example the recipients address, and so you may want to use both levels of security: message security will ensure the mail server (or any party except the recipient) can't read the content of your email, and transport security will additionally ensure that a third party listening in to the communications between you and your mail server can't find out who you're sending an email to (unless the mail server divulges that information to that third party).