Outlook 98 SMIME Problems

S/MIME Problems With Outlook "98

Reported May 8, 1998 by Russ Cooper on NTBugTraq

Systems Affected

Windows NT and Win9x, specifically the Protected Storage subsystem


A user has obtained a Digital Certificate from Verisign to use with S/MIME, and during installation, has chosen to set their security level to Medium (which means that each time their certificate is used, a dialog will appear informing them). Said certificate can be used to both digitally sign, and encrypt, a message sent from Outlook "98.

After creating a message and setting the options to sign & encrypt, the user presses the Send button. The message window closes and the Protected Storage dialog appears informing them of the use of their certificate. The dialog has 3 buttons and an X to close it. Ok, Cancel, and Details. The message is not acted on until this dialog is closed by clicking Ok, Cancel, or the X.

Based on the presentation of a Cancel button, the user decides (for whatever reason) that the action should not be completed. The natural assumption is that the message will not be sent.


The message is sent, and what"s worse, by clicking on the cancel button, the message is sent without encryption.

What happens is that the request to apply the digital certificate (and then use that mechanism to encrypt the message) is completely cancelled, but the message gets sent anyway.

The targeted recipients will receive a message that appears to have a digital certificate (they will see a little blue ribbon icon beside the message), but when they open it a dialog will appear indicating a problem with the signature of the message. This dialog lists a variety of information about the signing of the message that is supposed to be based on the presence of an actual signature. However, since the sender cancelled the use of their signature, no certificate is actually attached.

The receiver is told, for example, that the message;

- The signature is invalid

this makes sense, it was never signed

- The message is digitally signed

yet it isn"t

- The contents were not altered after it was signed

it was never signed, so how does it know this?

- The certificate is not revoked

it was never signed, so how does it know this?

- The certificate is not expired

it was never signed, so how does it know this?

- The certificate is trusted

it was never signed, so how does it know this?

- Email address on certificate is same as sender"s address

it was never signed, so how does it know this?

- There are other failure reasons

When there are other failure reasons Outlook states You can look at the problems with the certificate by selecting View Certificate, but the View Certificate button is grayed because there was no certificate!

To top that off, Outlook has a View Message button on this dialog. When you click that button Outlook displays the message that was sent, unencrypted.


The risks here should be obvious. When the original Protected Storage dialog box appears to inform you of the use of your certificate, users are going to believe that hitting Cancel is going to cancel their message entirely. If the message composed was intended to be encrypted, due to its sensitive nature, and they do hit Cancel, this sensitive information will be sent in clear text.

Further, no other information is provided to the sender. They are not informed that the message has been sent anyway unencrypted. If the recipient views the contents by using the View Message button, they are then able to reply to that original message. If they do reply, Encryption has been automatically dropped from the Options, but again, this has been done without notification to the user. Hence a conversation could carry on between the two individuals without either of them realizing that the messages were being sent unencrypted.

The warning dialogs do not explain to the recipient what is wrong with the message, just that its an invalid signature. Since they can still see the message (albeit by clicking a few unfamiliar buttons), they may obviously believe everything is proceeding.

Work Around:

One workaround for this issue is to not set the security level to Medium or High but to use Low instead. This prevents the dialog box from appearing at all, so its not possible to mistakenly send unencrypted messages in the fashion described above.

Unfortunately, this workaround introduces another exploit possibility. If the setting is set to Low, then a rogue process could cause a message to be created by your machine and sent, signed with your certificate, all without you knowing. The purpose of the Medium setting is to avoid precisely this possibility.

So in other words, you"re damned if you do and damned if you don"t.

Setting your security level to High is not a workaround. You will then be presented with numerous dialog boxes, none of which provide any useful information as to what is taking place (same true with the Details dialog at the Medium setting, it simply tells you that Outlook is trying to Read information from Protected Storage, not that its sending a particular message with contents blah blah).


The Cancel button must either cancel the message entirely, or should not be present. I prefer to see it cancel the message entirely. The reasoning is that should a rogue application actually create a message on my behalf and sign it with my certificate, not only do I want to know this has happened, but I want to prevent the message from being sent at all. When certificates are accepted for some important reason, the effort involved in explaining to the recipient why they received a message with my invalid signature is going to be too high.

If a message is going to be sent regardless, then two changes must be made to the current procedure:

1) The Details button must be able to display the contents of whatever has been signed/encrypted with my use of Protected Storage. Since there is no way to view the message from within Outlook at this point in the process, then this dialog must facilitate that.

2) The recipient Invalid Signature dialog box must not put pretty green check marks beside all of those things it has no way of confirming. Without a signature, it obviously cannot verify whether or not its valid, expired, revoked, or anything else. The false positive defaults for these items in that dialog are completely incorrect and lead to a false level of trust (gee, everything but other is Ok, I guess the message is mostly Ok!).


With the security level set to Medium, this appears to be a bug not an exploit. Users may take actions that they believe will have a different effect. Microsoft is already aware of this issue.

If this is not fixed swiftly (and I currently have an open incident with MS Premier Support Services on this issue), the use of S/MIME in Outlook "98 is seriously compromised. Other uses of Protected Storage and the Medium security setting have not been investigated, there may be other issues of more or less importance that this problem relates to (including the possibility that this may be used as an exploit).

To those that may suggest the use of PGP, Network Associates Inc. have confirmed that PGP will not be supported in Outlook "98 until some time between August and October of "98. While some aspects of PGP 5.5.2 do work well in Outlook "98, many ways of GP"ing PGP exist and its not a stable choice (not to mention that their support only provides best effort to resolve issues with Outlook "98).

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Reported by: Russ Cooper NTBugTraq
Posted here at NTSecurity.Net

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