Technical Documentation SEPPmail Outlook Add-In v1.5.3

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1 Technical Documentation SEPPmail Outlook Add-In v1.5.3 This document describes how the SEPPmail Outlook Add-in works and the settings that can be configured.

2 Page 2 Content 1 Introduction System requirements Installation Installation with user interface Installation without user interface Registry Local Machine Current User Mail Header fields Internal Encryption Automatic processing of s by the add-in... 12

3 Page 3 1 Introduction The SEPPmail Outlook Add-In (Add-in) can be installed on PC-systems with Microsoft Outlook. The installation can be performed in silent mode or with a user interface. Depending on the type of installation, different settings can be made, to influence the functionality of the Add-in. The Add-in provides new buttons to the user in all Outlook windows, where the user can compose mails. Depending on the settings that were chosen during installation, the number of buttons and their default states (pressed / not pressed) will vary. The states of the main buttons are put to the header of outgoing mails, when the mail is actually sent. An optional button calls a web site in the standard browser of the user. An optional setting will cause a warning, if a mail is sent unencrypted and unsigned. The Add-in supports multiple languages. The Add-in tries to use the language of the Outlook user interface. If that language is not present for the Add-in, then English is used as default language. The following chapters describe technical details about system requirements, installation procedures, registry settings and mail header details.

4 Page 4 2 System requirements Microsoft Windows: One of the following operating systems: Windows XP, Windows Vista, Windows 7 and 8 (32bit and 64bit) or Windows Terminal Server Microsoft Outlook: One of the following Outlook versions: Outlook 2000, Outlook XP, Outlook 2003, Outlook 2007, Outlook 2010 (32 bit and 64 bit), Outlook 2013 (32 bit).net Framework: The.NET Framework has to be present in version 4.0 Client Profile or newer. If it is missing, then the installation program tries to download and install the.net Framework from the internet.

5 Page 5 3 Installation There are two installation files: Setup.exe This file is required on Windows Vista, Windows 7 and Windows 8, if UAC is activated. For a manual installation, the user has to right click this file to choose Run as administrator. This file checks if necessary components (e.g..net Framework) are present for the installation. SEPPmailOutlookAddInSetup.msi Performs the actual installation. This file can also be run directly for the installation if sufficient rights are present (e.g. UAC is inactive and user has administrative rights) This file can also be used for automated software distribution. 3.1 Installation with user interface Example: 1. Right click on setup.exe choose Run as administrator. 2. Security Questions from the W indows system have to answered with yes.

6 Page 6 3. Then the setup wizard starts, and shows the screens that are shown below. On the screens the user can choose a. which buttons should be shown later on b. to activate / deactivate a warning if later on mails are sent unencrypted und unsigned. c. the default button states, when a mail window is later on opened.

7 Page Installation without user interface The installation can also be started via the command prompt with various settings as parameters. Important Note: The command prompt has to be started as Administrator!

8 Page 8 Example: msiexec /q /i "SEPPmailAddInSetup msi" SMWarning=false SMEncrypt=true SMSign=true SMWebmail=true SMHelp=true SMEncryptSelected=false SMSignSelected=false SMWebmailSelected=false /li.\log.txt Msiexec-Parameter: /q Installation without useri interface /i Installation of an msi-packet /li.\log.txt log.txt will be created in the current directory MSI-Parameter Parameter Default Description SMWarning False activate / deactivate warning for plain mails SMEncrypt True turn button Encrypt on or off SMSign True turn button Sign on or off SMWebmail True Encrypt with read receipt on or off SMNoEncryption False turn button No encryption on or off SMHelp False turn button Help on or off SMEncryptSelected False default state for Encrypt SMSignSelected False default state for Sign SMWebmailSelected False default state for Encrypt with read receipt SMNoEncryptionSelected False default state for No encryption Tooltips False turn tooltips for buttons on or off LMonly False store registry values only in Local Machine Subject-mod False If this option is active, control commands will be appended to the subject instead of writing them into header fields. Before sending a mail, all existing control commands are removed from the subject. Afterwards, new control commands are added according to the settings chosen by the user through the buttons in the add-in. As sent mails will then contain the control commands in the subject, the user can review

9 Page 9 them in his Sent mail folder for each mail. The following values are added to the Local Machine sub-tree. They configure the control commands that will be appended to the subject. s-smenc = [confidential] s-smsign = [sign] s-smwebmail = [priv]

10 Page 10 4 Registry 4.1 Local Machine During installation, registry values are only written to the node Local Machine in the registry. This is because the add-in is installed for all users of a PC / Terminal Server. By default the following settings are written to the registry: The path in the registry is: HKEY_LOCAL_MACHINE\SOFTWARE\SEPPmail\OutlookAddIn On a 64bit-System the following path will be used (because the setup project runs in 32-bit mode): HKEY_LOCAL_MACHINE\SOFTWARE\Wow6432Node\SEPPmail\OutlookAddIn In the registry path a sub-folder will be present with the name Tooltips In this subfolder, the tooltips are stored -each language has its own subfolder.

11 Page Current User If the setting LMOnly = false is used during installation (default value), then at start of Outlook a check is performed to see if there is already a registry node at: HKEY_CURRENT_USER\Software\SEPPmail\OutlookAddIn Or HKEY_CURRENT_USER\Software\Wow6432Node\SEPPmail\OutlookAddIn If that node is present, then the timestamp (UsageTimeStamp) value in that node is compared to the timestamp in the Local Machine section. If the settings in Local Machine are newer (or if there are no settings in the Current User section yet), then the following settings are copied from Local Machine to Current User. The UsageTimeStamp in Current User will be filled with the current time. In this way, it is possible to modify the above settings individually for a user, without changing the settings for other users. Is (at start of Outlook) the time stamp in Current User newer than the one in Local Machine, then the Add-in will use the settings from the Current User node.

12 Page 12 5 Mail Header fields When a mail is sent, then the following header fields are added to the header of the mail. The value will represent the state of the buttons. Tag x-smenc x-smsign x-smwebmail x-smplain Value yes/no yes/no yes/no yes/no 6 Internal Encryption The feature "Internal Encryption" allows to redirect sent s to an internal mailbox that provides (internal) server-side encryption. The following conditions must be satisfied in order for this feature to work correctly. The registry configuration value InternalRecipient has to provide the address of the mailbox that performs server-side encryption. By default, this is ime@imepseudodomain.local. Also, mails sent to ime@imepseudodomain.local by internal senders must be redirected to the SEPPmail Applicance (X-Headers must not be truncated!). When an is being sent, the entered recipients (To, CC, BCC) are removed and stored in header fields ("X-SM-ORIGTO", "X-SM-ORIGCC" and "X-SM ORIGBCC "). The configured server mailbox address ( InternalRecipient ) is set as the recipient to route the to the encryption mailbox. The server then is responsible for encrypting s that are received by the mailbox, for restoring the original recipients from the header fields and for re-sending the to the original recipient. 7 Automatic processing of s by the add-in The following processing steps are performed automatically by the add-in: - If an is sent with internal encryption, all original recipients (To / CC / BCC) are stored in header fields (and removed from the ), the mailbox address configured for the setting InternalRecipient is instead set as the recipient and a technical flag Internal encryption is set to the . - If an in the inbox has the flag X-ESWmail-InternalEncrypt-sentcopy set in its header, the technical flag Internal Encryption is removed and the e- mail is moved to the Sent Items folder. - If an is added to the folder Sent Items (e.g. by sending it) and has a technical flag Internal encryption set, this is deleted.

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