Troubleshoot e-mail security

Missing attachments

I see a paperclip icon next to a message, but when I open it, the attachment is gone.

You may have received a message that contains a level 1 e-mail security attachment file type. To prevent the inadvertent spread of viruses, Microsoft Outlook checks the file type of each attachment in a received message against the file types on the e-mail security attachment file type list. If an attachment is a file type that can contain code that can run without warning, you cannot see or access the attachment. Check the InfoBar at the top of the message to see the name of the file attachment you are unable to access.

My attachment is missing.

You have received a message that contains a level 1 e-mail security attachment file type. To prevent the inadvertent spread of viruses, Microsoft Outlook checks the file type of each attachment in a received message against the file types on the e-mail security attachment file type list. If the attachment is a file type that can contain code that can run without warning, you cannot see or access the attachment.

Check the InfoBar at the top of the message to see the name of the file attachment you are unable to access.

Note If you created a custom form that included a level 1 file type in the message body, your attachment will not be visible once you save and close the form. The InfoBar will not show the name of the blocked file attachment because custom forms do not display the InfoBar.

The shortcut I sent to others has disappeared from their messages.

Shortcuts with a file extension of .lnk or .url are level 1 e-mail security attachment file types.áTo prevent the inadvertent spread of viruses, Microsoft Outlook checks the file type of each attachment in a message you send against the level 1 file types on the e-mail security attachment file type list. If the attachment file type is level 1, recipients cannot see or access the attachment. Recipients can verify that this is why they are not seeing the shortcut by checking the message's InfoBar to see if it displays the name of your shortcut. You can then send them a message with a text link instead of the shortcut.

Unavailable menu commands

The View Attachments command on the shortcut menu is unavailable.

The Save Attachments command on the File menu is unavailable.

You have received a message that contains a level 1 e-mail security attachment file type. To prevent the inadvertent spread of viruses, Microsoft Outlook checks the file type of each attachment in a received message against the file types on the e-mail security attachment file type list. If the attachment is a file type that can contain code that can be run without warning, you cannot access the attachment. The InfoBar will display the name of the file attachment you are unable to access.

Encrypting and digitally signing messages

I can't send an encrypted message.

You might not have a copy of the intended recipient's digital ID. To send an encrypted message to an Internet recipient, you must add a copy of their digital ID stored with their address in your Contacts folder or Address Book.

How?

Open a message that has a digital ID attached.
Right-click the name in the From field, and then click Add to Contacts on the shortcut menu.
If you already have an entry for this person, select Update new information from this contact to the existing one.
The digital ID is now stored with your contact entry for this recipient. You can now send encrypted e-mail messages to this person.
To view the certificates for a contact, double-click the person's name, and then click the Certificates tab.

Signed messages display an error when I open them.

When a signed message that uses a certificate fails, a message appears that describes the problem. Click Details for more information about the specific problem.
You may need to change the trust levels for the sender. In the Certificate dialog box that appears, click Edit Trust, and then click Explicitly trust this certificate.
The sender's certificate may have expired. In the Certificate dialog box that appears, click Details, and then click View Certificate. Click the Details tab, and then look at the Valid from date.

My message format changed when I sent a secure message.

If you are using Microsoft Exchange Rich Text Format for messages, and you send a secure message that uses an S/MIME digital ID, the message format is changed to HTML to ensure correct processing of the digital ID. Some formatting may be lost in the conversion.

I can't open a secure message that was sent to me.

When a secure e-mail message does not open properly, a message appears that describes the problem. For more information, click Details on the message.

You might have to change the trust levels for the sender. In the Certificate dialog box that appears, click Edit Trust, and then click Explicitly trust this certificate.

The sender's certificate might have expired. In the Certificate dialog box that appears, click Details, and then click View Certificate. Click the Details tab, and then look at the Valid from date.

I receive a message when I try to send secure e-mail.

If you receive the message: ôThe Security Policy you selected does not allow one of the certificates in this security profile to be usedö it means that the certificate in your default security settings has expired or has otherwise become invalid, or that your security policy does not accept your certificate. If you have set your security options to use labels on every message you send, the automatic configuration will not automatically notify you that your certificate has become invalid. To ensure that the automatic configuration notifies you of problems with your default certificates, on the Tools menu, click Options, and then click the Security tab. Click Settings, and then click Security Labels. In the Policy module list, click None. If your security system does not allow you to choose None, contact your administrator to get the correct certificates for your system.
If you receive the message: ôMicrosoft Outlook had problems encrypting this message because the following recipients had missing or invalid certificates, or conflicting or unsupported encryption capabilities" the most common cause is that you tried to send encrypted e-mail without having a copy of a valid certificate for the recipient. If you have multiple contacts for the recipient, you must send e-mail using the contact that has the certificate.

I get a signature failure message when I try to open e-mail messages.

When a secure e-mail message does not open properly, a message appears that describes the problem. Click Details for more information about the specific problem.

You might have to change the trust levels for the sender. In the Certificate dialog box that appears, click Edit Trust, and then click Explicitly trust this certificate.

I sent a message with a secure receipt request but received no return receipt.

A secure receipt is not returned if:

Your signature on the message is not verified by the recipient's security system. This happens if the certificate is not trusted.
The recipient may have chosen not to send receipts when requested.

My security label settings have disappeared from Outlook.

You have changed your default security setting from S/MIME to Exchange Server security. Security labels, clear text signed messages, and secure receipt requests require that S/MIME be your default security format. On the Tools menu, click Options and then click the Security tab. Click the Settings button. In the Secure message format list, click S/MIME.

Why are the security label settings unavailable?

You must have a security policy module installed. Contact your administrator.
You must digitally sign the message. In the message, on the File menu, click Properties, and then click the Security tab. Click the Add digital signature to message check box.
If the privacy mark, classification, or other settings are not available, it may be because of settings specific to the policy module. Contact your administrator.
You must be using S/MIME as your default security format. To change your default security format, on the Tools menu, click Options and then click the Security tab. Click the Settings button. In the Secure message format list, click S/MIME.

Why can't I publish my certificates to the Global Address List?

Your server may be unavailable. Send a test message addressed to yourself to see if your server is working.
You may not have permission to write to the Global Address List. Contact your administrator.
The security policy you are using may not allow the Publish to GAL button to appear. If the button is unavailable, contact your administrator.

Why can't I send a secure receipt request?

You must be using a version of Microsoft Windows that supports this feature. The supporting versions are Microsoft Windows 2000 or later, Microsoft Windows Millenium Edition (Me), or later.
You must have a valid security profile, including a valid digital ID (certificate), to send a secure receipt request.
If you are using an Internet e-mail account, such as POP3, a secure receipt request is not sent until you click the Send/Receive button on the Outlook toolbar.

Why can't the recipient of my labeled message open the message?

Security labels appear only on messages sent and received by users who use Microsoft Windows 2000 or Microsoft Windows Millennium Edition (Me). If you send a message with a security label to a recipient who uses a previous version of Windows that doesn't support this feature, they will not be able to open the message.
If recipients do not have the appropriate policy module, they may not be able to open the message.

Other

I'm having problems synching my Handheld PC or cell phone.

When you synchronize your Handheld PC, cell phone, or other device, you will be prompted to allow the program to access your Address Book and contacts.áBecause viruses can spread by sending copies of e-mail messages to people listed in your Address Book, Microsoft Outlook e-mail security prevents programs from programmatically accessing your Address Book and contacts. Before the synchronization can continue, you must allow access to your Address Book. You can allow unsecured access for a specific instance (such as for one contact) or for a specified time period of up to 10 minutes.

You may also receive error messages while synchronizing or when sending e-mail from some Handheld PCs.

None of the ActiveX Controls, Java applets, or scripts I receive in HTML mail work.

Your security zone setting is set to the highest security level by default, which disables all active content in HTML messages.