============================================================================== ======|ЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇЇ|====== ======| ClickOnce Man-In-The-Middle email@example.com |====== ======|__________|====== ==============================================================================
============================================================================== ======[ Introduction ]================================================== ==============================================================================
"ClickOnce deployment allows you to publish Windows-based applications to a Web server or network file share for simplified installation." 
As has been previously shown - applications that update, depending on implementation, can be vulnerable to man-in-the-middle attacks. ClickOnce, depending on opinion, ranges from moderately vulnerable to very vulnerable. Borrowing heavily from Moxie's presentation on Defeating SSL, the feedback given to a user when you subvert ClickOnce's security is extremely subtle and does not fully explain the situation. In some cases, it can be argued it is far more permissive than it reasonably could be.
============================================================================== ======[ Implementation ]================================================ ==============================================================================
ClickOnce is most commonly deployed onto a web server (IIS or otherwise). Users visit the website, usually using Internet Explorer. There they click on a link to a .application file that will prompt them to install the ClickOnce application. (The semi-trojan Firefox plugin ".Net Framework Assistant" Microsoft installed without permission was to enable the same functionality in Firefox.)
For the purpose of simplification we will consider the simpler case of a single-assembly deployment. Multi-assembly deployments are also vulnerable.
The .application file is an XML file containing:
The browser reads the .application file and (usually) presents the user with a dialog to install the ClickOnce application. (The exception being elaborated upon later.)
The installer will download a .manifest file and a .deploy file. The .deploy file is the ClickOnce exe. The .manifest is an XML file consisting of the following relevant items:
Windows installs the application. Depending on the update frequency specified in the .application, the ClickOnce framework will check the .application file on the web server and compare the publish version.
If a newer version is available, the user will be prompted to update. If the update is indicated to be required, the user's options are to update or exit.
============================================================================== ======[ Code Signing ]================================================== ==============================================================================
ClickOnce supports Authenticode. Authenticode is a small non-wrapper on top of X.509 certificates. The standard CA chain applies to the certificates, with one of the CAs on the chain being installed in your store of trusted CAs.
When the application is signed, the certificate is included in the .application and .manifest files, and if the certificate validates (by having one of the CAs in the chain installed in your store) the publisher name specified in the certificate is presented in the dialog box upon install.
If a certificate expires, the signature will still be considered valid, because a timestamp is embedded in the signature. The certificate is checked to be valid during the timestamp. The neatly avoids orphaned apps.
The signing occurs before publishing the ClickOnce application. You have the option to sign the .manifest and .application independently of signing the assembly(ies). Microsoft recommends signing the .application and .manifest but not the assemblies. Signed assemblies cannot reference unsigned assemblies, and this may complicate your deployment.
============================================================================== ======[ Man-in-the-Middle ]============================================= ==============================================================================
The simplest case of MITM-ing ClickOnce is a rewriting an unsigned dll. Using techniques inspired by and borrowed from Erez Metula's Re-Frameworker tool, the following steps are necessary for a dll rewrite on the fly:
Despite the <hash> attribute missing, the ClickOnce installer will install the application seamlessly. During testing, seeing the logs of failed installs, I observed that the omission of the <hash> element caused a warning. But it does not display to the user or otherwise indicate any problems were encountered.
ClickOnce provides a very simple update mechanism with all the plumbing taken care of and minimal effort required by the user or the administrator. It may be advantageous to use this update mechanism to deploy more sophisticated (malicious) code to the client. If the benign ClickOnce application does not specify an update frequency to your liking, you can rewrite the .application file before sending it to the client and specify it should check for updates upon every startup.
I am taking a slight detour to discuss the three dialogs displayed to the user under different circumstances, as they are referenced in the next several sections.
The "Update Available" dialog is shown here: http://www.devx.com/codemag/Article/30460/1763?supportItem=5 This dialog indicates that there is an optional update available.
The Install dialog is shown here, in Figures 1 and 3: http://msdn.microsoft.com/en-us/library/ms996418.aspx#clickoncetrustpub_topic2 One of two icons are shown at the bottom of the dialog: a yellow exclamation point icon or a red X icon.
The factors that determine this icon are:
The two combinations we are most concerned with are: - Untrusted Publisher + Partial Trust + Installed + From Internet = Yellow - Untrusted Publisher + Full Trust + Installed + From Internet = Red
I will define a term "Increasing Risk" to mean that one of these elements increased in risk. Examples are going from Partial to Full Trust, or changing the signing key used. (Changing the signing key includes removing it.)
The .manifest file specifies the permissions required by the ClickOnce application. If the permissions are not to your liking, you can modify them. But rather than mess with individual permissions, it's easier to short-circuit the argument and require Full Trust.
Full Trust implies that the application is able to do anything the User Account can do. Fully Trusted code is able to bypass many of the mechanisms built into .Net that intend to limit code, including ignoring the type system, bypassing class protection levels, disabling code access security, and jumping App Domains . Full Trust is still limited by the User Account - Operating System limits on file access, service control, and administrative options still apply.
In the Untrusted Publisher case, elevating trust Increases Risk, and will show the install dialog to the user, almost certainly the red-icon variant based on the type of activity you're likely to do.
If a ClickOnce application checks for updates before startup, you can require the user update the application or it will not run. Besides requiring the user to install your new code, you can also Denial-of-Service the user in several ways - requiring an update but withholding or corrupting the .deploy, corrupting or otherwise messing with the configuration files, or others.
The Forced Update is implemented by specifying that an update is available, and that the minimum required version for the update is greater than what they currently have. For Example:
Installed on Client: 184.108.40.206 Version of Update: 220.127.116.11 Minimum Required Version: 18.104.22.168
A Forced Update that does not Increase Risk (meaning the trust level stays the same and the signing key does not change) will install with no prompts.
A Forced Update that Increases Risk (by elevating trust or changing the signing key) will show the user the install prompt.
You can rewrite the url the ClickOnce Framework will use to see if an update is available. This can be accomplished by a MITM attack on the .application in transit, or by using another vulnerability to edit the xml file on the deployment server.
Changing the signing key will cause Update Redirection to fail, as the publisher identity has lost both pieces it needs (key-matching and url-matching). The program will be prevented from starting, displaying an error. The scenarios are spelled out explicitly:
If you are MITM-ing a session, and want to achieve the second scenario (for example, you want to point them to your server so you do not have to keep the MITM session open), a two-step process is recommended:
It would be simple to write a set of services that watch public ClickOnce deployments, mirror them with malicious code, and having subverted .application files point to these repositories. Your server can watch for updates from the legitimate server, download & infect them, and make them available to clients. Depending on the latency of your processes, it could be seamless to the end-user and ClickOnce administrator, them never knowing you've bypassed their infrastructure.
When a ClickOnce application is signed using a valid code-signing certificate AND the certificate has been installed in the user's Trusted Publisher Store the ClickOnce Application will install with no prompts. Adding a certificate to the Trusted Publisher Store is detailed in . This is almost-never done outside of corporate environments. (And may not be done inside of them.) Otherwise, the Install Dialog is presented to the user.
It's my opinion that since users are used to seeing some warning message when installing applications the Install Dialog is not a huge obsticle to overcome, even if it is the red-icon variant. The user is likely to click the Install button.
Removing the signed-ness of a ClickOnce Application consists of the following steps:
It is understandable that for a first-install of a ClickOnce application, removing the signed-ness would work, because the client is unaware that the application should be signed.
But removing the signed-ness of a ClickOnce application in an update-scenario also works. In detail:
This technique is inspired by Moxie Marlinspike's sslstrip tool - the idea being if the security is getting in the way of the exploit - remove it, and no one will notice.
============================================================================== ======[ Conclusion ]==================================================== ==============================================================================
Upon the initial install, or an update, of a ClickOnce Application we are able to:
Using a two-step process we can also:
The user's experience while doing this is a non-threatening dialog asking them if they 'are sure [they] want to install this application'.
============================================================================== ======[ Mitigation ]==================================================== ==============================================================================
The only mitigation for these problems is only deploying ClickOnce applications from a well-managed server over HTTPS. No amount of signing is useful unless the application is deployed over SSL/TLS.
Microsoft should investigate the several lapses of the ClickOnce Framework (accepting dll's without hashes, accepting a mis/un-signed update to a signed application) and evaluate what scenarios they would break by increasing security.
============================================================================== ======[ Recent Developments ]=========================================== ==============================================================================
On July 12, 2010 Codeplex, Microsoft's Open Source Project Community, announced they would support hosting ClickOnce Releases. They do not host on HTTPS (example: http://pull.codeplex.com/releases/view/48962 ).
============================================================================== ======[ Thanks, Greets ]================================================ ==============================================================================
Prior Art: [2,8,11] 64782154e80d504253f8b13ce6ef422d891a4522ffafe9c9ea6414559f47b9a1 7796f79804733765d22de3cec807de7dd20c79f3a366c400114c96f2d36eef68 0dd19e1fea39939cd34b70364d0f346960f6bba606fc6c22598a65dbdeada35d 3e648d010c71255005368a6b26cfba3ed995e1e59efba7a609e7e94473ce95d0
============================================================================== ======[ Footnotes ]===================================================== ==============================================================================
 http://msdn.microsoft.com/en-us/library/t71a733d(VS.80).aspx  CVE-2006-4567  http://defcon.org/html/links/dc-archives/dc-17-archive.html#Marlinspike  http://blogs.msdn.com/b/brada/archive/2009/02/27/uninstalling-the-clickonce-support-for-firefox.aspx  http://msdn.microsoft.com/en-us/library/ms537359(VS.85).aspx  http://msdn.microsoft.com/en-us/library/ms172240(VS.80).aspx  http://msdn.microsoft.com/en-us/library/h4fa028b(v=VS.80).aspx  http://www.appsec.co.il/Managed_Code_Rootkits  http://msdn.microsoft.com/en-us/magazine/cc163990.aspx  http://msdn.microsoft.com/en-us/library/ms172241.aspx  http://www.thoughtcrime.org/software/sslstrip/  http://blogs.msdn.com/b/codeplex/archive/2010/07/13/clickonce-releases.aspx