DRACOON for Outlook version 6.3 or later
In special cases, such as emails with the highest security requirements, you can send a complete email protected as a DRACOON share with DRACOON for Outlook. The contents of the email as well as any attachments are uploaded to a data room in DRACOON. Your actual email message including attachments will not be sent by Outlook via email—instead, the recipient will receive an info email with instructions on how the email with attachments can be downloaded from DRACOON via the share link.
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About Email Protection in DRACOON for Outlook
Security concerns: Regular email sending
Sending email in the usual way is not secure: Normally, when you send an email, it is first sent from your organization's outgoing mail server and then remains in your inbox (in the Sent Items folder) as a copy. The email is transmitted to the recipient's email server, where it is stored in the inbox. Unless you have encrypted the email with your mail program, the email is transmitted in plain text and can theoretically be intercepted by an administrator or intruder who has gained access to one of the mail servers - both on the part of your organization (outgoing mail server) and on the part of the recipient (incoming mail server). Sending highly confidential messages via email is therefore a potential security risk.
It is possible to enable email encryption (via S/MIME) in Outlook for additional security. However, this requires the exchange of certificates between sender and recipient and is therefore complex and error-prone.
More secure: Sending emails with Email Protection from DRACOON for Outlook
If you send an email with Email Protection from DRACOON for Outlook, the contents of your email and any attachments are not sent in the above way (via several mail servers involved) and also not stored in your mailbox and that of the recipient. Instead, before sending, both the contents and any file attachments of your email are uploaded to a data room in DRACOON and removed from the original email. The email that is finally sent is merely an info mail with the note where the original email with any attachments can be securely downloaded from DRACOON via a (password-protected) share link.
Most secure: Sending emails with Email Protection from DRACOON for Outlook with additional client-side encryption
For maximum security, you can specify that the protected email including attachments should be stored in an encrypted data room in DRACOON. Your email including attachments is then additionally encrypted on your PC and only decrypted again after the email has been downloaded by the recipient. This ensures that not even DRACOON as a provider could decrypt and read the email contents including attachments.
- Contents and attachments of an email sent with Email Protection by DRACOON for Outlook are not sent via your mail server and therefore cannot be accessed by server administrators.
- Furthermore, they are not stored in the recipient's mailbox, so that no data can be leaked by server administrators, for example, on the recipient side.
- If an encrypted data room is selected as the storage location for the email in DRACOON, client-side encryption ensures that contents and attachments of the email are already securely encrypted on the sender's PC before they are uploaded to DRACOON—due to the client-side encryption, even DRACOON personnel would not be able to decrypt the email under any circumstances.
- An expiration date can limit the availability of the email so that it cannot be downloaded and opened by the recipient afterward. If necessary, the share of the email can also be terminated at any time by deleting the share link.
- Sender and recipient do not have to exchange certificates, as is required for the mail encryption included in Outlook (via S/MIME). The sender only has to forward the share password to the recipient.
- The share setting "Notify on download" results in a read receipt, which the receiver—in contrast to the usual read receipt of email clients—cannot prevent.
You can choose between two formats in which a protected email from DRACOON can be provided to the recipient:
- As EML file for download (default)
The recipient can open the EML file after downloading it from DRACOON with an email program by double-clicking, for example.
Pros: Display in familiar view in the email program (e.g. in Outlook), immediate reply to the email possible using the email program
Cons: Email program that can open EML files required. Therefore, may not be usable on mobile devices - As PDF file for instant view
The recipient can read the email as a PDF file directly in the browser (Exception: For encrypted data rooms, the PDF file must first be downloaded from DRACOON).
Pros: No additional software required to open the file, usually direct viewing of the PDF file from DRACOON in the browser possible (download is only required for encrypted data rooms). Thus, email can also be read on all mobile devices
Cons: Direct reply to the email via an email program not possible (the email is an independent PDF file)
Send a complete email message including attachments protected as a DRACOON share
- You plan to send an email that has special security requirements and therefore should not be sent as a regular email but protected as a DRACOON share.
In the Outlook ribbon, in the DRACOON section, click Email Protection so that the lock icon has a green checkmark: - Compose your email as usual and add attachments if necessary. If you attach files to the email, they will automatically be converted to DRACOON share links.
- Send the email.
- If you send an email protected as a DRACOON share for the first time, it is not yet known where in DRACOON the email and its attachments should be stored.
In this case, DRACOON displays the message "To send protected emails, please select a target folder or room" and then opens the settings for Email Protection: - Click Browse and select a data room or folder in DRACOON where you want to store your protected emails including attachments in the future.
If maximum security is required, select an encrypted data room, if available (you can recognize encrypted data rooms by an additional lock icon):
- Click OK to save your settings as the new default.
- A dialog box appears where you are asked if you want to set a password for the protected email:
While it is possible to send a protected email without password protection (unless you have selected an encrypted data room as the location—in which case a password is mandatory), this is not recommended for security reasons!
We recommend specifying a password for the share that the recipient of the share must enter later to read your email. Enter a password yourself or click the button to automatically generate a secure password. - Click the button to copy the password to the clipboard.
- Done! DRACOON for Outlook converts your email message to an EML or PDF file and uploads it to the previously selected data room or folder in DRACOON.
If you had attached files to your email, they will also be uploaded to DRACOON.
Afterward, DRACOON for Outlook creates a share for the EML or PDF file of your email message and separate shares for each email attachment.
The recipient of your email will not receive your actual email but a special notification email with the share link and a short instruction on how to download the email from DRACOON. - Important: Notify the recipient (e.g. via chat or separate unprotected regular email) that you have sent a protected email to him and that he can safely download and open it from DRACOON.
Be sure to forward the sharing password you specified in step 7 above or in Settings > General to the recipient—otherwise, the recipient will not be able to access the file containing your email and attachments. For example, you can send the sharing password you copied in step 8 above to the recipient by chat message, and paste it into a chat by pressing
Ctrl
+V
. In case you have missed copying the sharing password and don't remember it, you can create a new share for the email EML or PDF file with a new password in the DRACOON Web App and then forward it along with the new share link.
Option: Ask for password and sharing settings each time instead of using defaults
If you send a protected email as a DRACOON share, a default password (if any) specified under Settings > General and any default settings specified under Settings > Email Protection are automatically applied (such as an expiration period that should apply to all protected emails). This allows you to quickly send emails protected as shares without the need to confirm dialog boxes each time.
However, if you want to specify different sharing settings (e.g. a different expiration date or a different data room in DRACOON) for each protected email, change the following setting:
- In the Outlook ribbon, in the DRACOON section, click Settings:
- In the navigation pane on the left, click Email Protection, and then click Ask every time:
- Each time you send an email protected as a share, the following dialog box will be displayed in which you can explicitly specify settings for the email that may differ from the default settings (You may need to first expand the Advanced section at the bottom to see all the available settings):
Format for protected emails in DRACOON
You can choose between two formats in which a protected email from DRACOON can be provided to the recipient:
- As EML file for download (default)
The recipient can open the EML file after downloading it from DRACOON with an email program by double-clicking, for example.
Pros: Display in familiar view in the email program (e.g. in Outlook), immediate reply to the email possible using the email program
Cons: Email program that can open EML files required. Therefore, may not be usable on mobile devices - As PDF file for instant view
The recipient can read the email as a PDF file directly in the browser (Exception: For encrypted data rooms, the PDF file must first be downloaded from DRACOON).
Pros: No additional software required to open the file, usually direct viewing of the PDF file from DRACOON in the browser possible (download is only required for encrypted data rooms). Thus, email can also be read on all mobile devices
Cons: Direct reply to the email via an email program not possible (the email is an independent PDF file)
Advanced sharing settings for emails
You can specify the following settings when sharing emails:
- Notify on download: You will receive a notification email every time someone downloads your shared email or one of its attachments.
- Limit number of downloads: Specifies that the email can only be downloaded x times via this share. This restriction applies to the mutual downloads of all users of the share. Once the limit has been reached, no further downloading is possible.
- Link to email expires after: Specifies that the share is limited in time. The date determines the last day on which the share can still be used and therefore the email can still be downloaded. After that, the share will be automatically deleted. If you do not activate this setting, the share remains active until you delete it manually, for example, under Shares.
The additional setting Delete protected emails and attachments after the link expires causes the email and its attachments to be deleted from DRACOON permanently after the expiration of the share. If this setting is not activated despite an expiration date has been specified, the email will remain permanently in DRACOON but cannot be downloaded or viewed via the share after the expiration date.
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