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Cemaphore Systems, Inc.

MailShadow for
Google Apps
(Beta 1)
User Guide and Known Issues
List
6/17/2008

Copyright 2008 Cemaphore Systems, Inc. All


Rights Reserved
Cemaphore Systems Confidential and
Proprietary
MailShadow for Google Apps (Beta 1) User Guide and Known Issues List

Contents
Top 6 Known Issues.........................................................................................................................3
Pre-Installation Steps and Pre-requisites.........................................................................................5
Configuring your Test Outlook Profile (Outlook 2003) If Using a Test Exchange Mailbox..........7
Configuring your Test Outlook Profile (Outlook 2007) if Using a Test Exchange Mailbox...........9
Checking Your Gmail Account......................................................................................................11

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MailShadow for Google Apps (Beta 1) User Guide and Known Issues List

Before Installing MailShadow for


Google Apps (Beta 1)
This is early Beta release code. As such, we
strongly recommend that you execute a full
PST export/back-up of your Exchange Mailbox,
including email, calendar, contacts, and other
data items, using the export (file type .PST)
feature in Outlook, before installing and
running MailShadow for Google Apps (Beta 1).

Top 6 Known Issues

1. Some Email Duplicates Created for BlackBerry Users:


MailShadow for Google Apps Beta 1 can cause duplication of certain
email message in the inbox if the user’s mailbox is being synced to a
BlackBerry handheld device by a BlackBerry Enterprise Server (BES).
We are working to mitigate this issue.

2. Outlook Subfolders with Path + Name Greater Than 40


Characters Don’t Sync to Gmail: This is a limitation on the Google
side. If you want to sync those folders, we recommend you reduce the
levels of nesting in your Outlook hierarchy and/or reduce the sizes of
folder names, to bring the total path + folder name character count to
40 or less.

3. Username/Password
Credentials for Google
Not Accepted
Repeatedly: If the
MailShadow prompt for
Google credentials
repeatedly fails, your
Google account may have
entered what is called a
“Captcha Lockout” state.
You can perform a “Captcha
Unlock” of your Google
account by logging into
your Gmail account via web

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MailShadow for Google Apps (Beta 1) User Guide and Known Issues List

browser and responding to the prompt for entering the text shown in
the image on the page.

4. Email Items Older Than 30 Days Won’t Sync to Gmail: this is by


design in Beta 1. Only the last 30 days of existing email, plus new
emails, all existing/new Contacts, and all existing/new Calendar items
are synced to Google in Beta 1. Modifications (such as moves, deletes,
edits) are also synced bi-directionally.

5. Outlook Performance Impacted Under Certain Circumstances:


Outlook performance is known to be adversely impacted while using
MailShadow for Google Apps (Beta 1) under the following conditions:
(1) When deleting large numbers (100+) of items in Outlook in one
bulk delete operation; (2) When the network latency between the
Outlook computer and Gmail is high (e.g., greater than 200 msec
roundtrip ping time) or when the network goes up and down
repeatedly; (3) when changing an entire Outlook folder to the “read”
(vs un-read) state in bulk, and (4), when performing bulk move (i.e.,
hundreds of items) operations in Outlook. Feedback on user
experience is greatly appreciated as part of the Beta 1 program.

6. Calendar & Email Sync Rate/Count Limit on Google: The Google


email and Calendar have a governor or limit on the number of calendar
Item or email write transactions they will accept in a given period of
time and a limit on the maximum item count. The limits are not
published by Google. This can cause MailShadow for Google Apps sync
to sometimes not fully sync all Calendar items or to take longer than
expected to fully sync all email data to Gmail.

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MailShadow for Google Apps (Beta 1) User Guide and Known Issues List

Pre-Installation Steps and Pre-requisites


1. You may run MailShadow for Google Apps using a test Exchange
mailbox and test Outlook profile, or you can run it against your
production Exchange/Outlook mailbox.

If you wish to use a test account, have your Exchange Administrator


create a test user account in your Exchange environment (production,
test, or lab) to use with MailShadow for Google Apps (Beta 1) testing.
Your Exchange Administrator must provide you with an Exchange
server name, user name (e.g., John Smith), login (e.g., jsmith), and
password.

If you intend to use your production Exchange/Outlook account, please


execute a full .pst export/back-up of all your mailbox data using the
Outlook/File/Import and Export utility. This will enable you to restore
your data in the event of data loss or corruption during Beta testing.

2. Create a test Gmail account on Google to use for beta testing if you
don’t already have one. You may user a Google Apps Premier account
or a personal Gmail account for Beta testing.

3. Via web browser, log into the Gmail account and enable IMAP
forwarding as shown below:

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MailShadow for Google Apps (Beta 1) User Guide and Known Issues List

John.Smith@acme.com

4. In Gmail/Settings, go to “Forwarding and POP/IMAP” and select


“Enable IMAP”.

5. In Google Calendar/Settings/Notifications, remove the default


notification (10 minutes prior to meeting), and deselect notifications
for New Invitations, Changed Invitations, Cancelled invitations,
Invitation Replies, and Daily agenda.

6. Ensure your Desktop/Laptop Meets the Following Minimum System


Requirements:
a. Supported Operating System: Windows XP (32-bit) Only
b. Microsoft Outlook 2007/2003 only
c. Hard Disk Space: 1.01Gb (10Mb for product, 1Gb for log files)
d. RAM: At least 250Mb free when Windows XP and Outlook are
running before installing the MailShadow for Google Apps (Beta
1)
e. CPU: > 1.2Ghz, AMD or Intel

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MailShadow for Google Apps (Beta 1) User Guide and Known Issues List

Configuring your Test


Outlook Profile (Outlook
2003) If Using a Test
Exchange Mailbox
1. Shut down Outlook if running.

2. Go to Control Panel/Mail

3. Select “Show Profiles”

4. Select the “Prompt for Profile to be


Used” radio button

5. Select “Add Profile”

6. Name the profile. Call it


something unique so you don’t
confuse it with any other Outlook
profiles you may already have
configured. Click OK.

7. Select the Add a new e-mail account


radio button and click Next

8. Select the Microsoft Exchange


Server radio button and click
Next.

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MailShadow for Google Apps (Beta 1) User Guide and Known Issues List

9. Input the Exchange server name


that is hosting the test mailbox.
Note: Use Cached Exchange
Mode Only with MailShadow
for Google Apps (Beta 1).

10.Input the name for the test user


account provided to you by your
Exchange Administrator.

11.Click Check Name, wait a


minute or so for it to check the
name. If the name doesn’t
check out, contact your
Exchange Administrator to troubleshoot.

12.Once the Check Name returns successfully, Click Finish.

13. Start up your Outlook client and select the new profile you just
created, then log in using the test account logon credentials provided
by your Exchange administrator. Do not run MailShadow for
Google Apps on any other Outlook profile or you may wind up
inadvertently syncing your real Outlook data to Gmail.

14.Outlook should connect to your test Exchange mailbox.

15.Verify Outlook/Exchange functionality with the test mailbox:

a. Send a test message FROM this email account in Outlook to


verify Send functionality.
b. Send a test message TO this account from another account to
verify receive functionality.
c. Create and save one or more contact and calendar items in
Outlook.

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MailShadow for Google Apps (Beta 1) User Guide and Known Issues List

Configuring your Test


Outlook Profile (Outlook
2007) if Using a Test
Exchange Mailbox

1. Shut down Outlook if running.

2. Go to Control Panel/Mail

3. Select “Show Profiles”

4. Select the “Prompt for Profile to


be Used” radio button

5. Select “Add Profile”

6. Name the profile. Call it something unique so you don’t confuse it with
any other Outlook profiles
you may already have
already configured. Click
OK.

7. Select “Manually configure


server settings…..” then click
next.

8. Select “Microsoft Exchange”


then click next.

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MailShadow for Google Apps (Beta 1) User Guide and Known Issues List

9. Input the Exchange


server name that is
hosting the test mailbox.
Note: Use Cached
Exchange Mode Only
with MailShadow for
Google Apps (Beta 1).

10.Input the name for the


test user account
provided to you by your
Exchange Administrator.

11.Click Check Name, wait


a minute or so for it to
check the name. If the
name doesn’t check out,
contact your Exchange
Administrator to
troubleshoot.

12.Once the Check Name


returns successfully,
Click Finish.

16. Start up your Outlook client and select the new profile you just
created, then log in using the test account logon credentials provided
by your Exchange administrator.

Note: Only run MailShadow for Google Apps on


one Outlook profile at a time, or you may wind

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MailShadow for Google Apps (Beta 1) User Guide and Known Issues List

up inadvertantly syncing data from multiple


Exchange accounts to one Google account.

17. Outlook should connect to your test Exchange mailbox.

18.Verify Outlook/Exchange functionality with the test mailbox:

a. Send a test message FROM this email account in Outlook to


verify Send functionality.
b. Send a test message TO this account from another account to
verify receive functionality.
c. Create and save one or more contact and calender items in
Outlook.

Checking Your Gmail Account


1. Log in to the test Gmail account you set up for this Beta 1 test.

2. Ensure the “Enable IMAP” option is checked under Gmail/Settings/Forwarding


and POP/IMAP

You are now ready to install and run MailShadow for Google Apps
(Beta 1).

Please proceed to next page for installation instructions.

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MailShadow for Google Apps (Beta 1) User Guide and Known Issues List

Installing MailShadow for Google


Apps (Beta 1)
1. Download the MailShadowForGoogleAppsBeta1.zip package from the
address provided to you by Cemaphore, onto the machine containing
the Outlook test profile created in the pre-installation instructions.

Note that the End User License Agreement (EULA) limits you to
installation of MailShadow for Google Apps (Beta 1) on only
one computer. You may not create copies of the software or
distribute the software or this document to anyone else.

2. Unzip and run MailShadowForGoogleApps.exe installer package.

3. Follow the install instructions. You’ll be prompted for your Gmail


account credentials.

4. The installer will create a Cemaphore item in the All Programs List as
shown below, and MailShadow will be enabled by default.

5. Restart Outlook with the Outlook profile you wish to use for Beta
testing.

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MailShadow for Google Apps (Beta 1) User Guide and Known Issues List

John Smith

6. You should see a


MailShadow for Google Apps
splash screen in front of
Outlook. The splash screen
can stay up for as much as
60 seconds the first time it
initializes. The splash
screen also shows you how
many days are left before
the Beta 1 software expires.

7. After the splash screen disappears, wait for Outlook to fully load and is
connected to Exchange. This is confirmed when you see “connected”
in the lower right corner of the Outlook user interface.

8. Use Outlook normally: Send and receive Outlook email, create and
save new contacts, and create and save calendar items. Since this is
beta code, you may notice some degradation in the performance of
Outlook.

9. Log into your Gmail account via web browser and watch the Outlook
items sync over. Give it a few minutes the first time you initialize. For

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MailShadow for Google Apps (Beta 1) User Guide and Known Issues List

larger mailboxes, initial sync of all your day may take several hours or
even days.

Begin sending emails, and create contacts and calendar items, and
watch them sync back to Outlook.

10. Make changes to existing items in either Outlook or Gmail/Google


Calendar and watch the changes sync back to the other side. You are
now using MailShadow for Google Apps (Beta 1) to keep your email,
calendar, and contact items synced between Outlook and Gmail,
Google Calendar, and Contacts.

11. You can disable and re-enable MailShadow for Google Apps (Beta 1)
from the All Programs menu by going to /Cemaphore/Disable (or
Enable) MailShadow for Google Apps menu. Outlook should be shut
down prior to disabling or enabling. Note that disabling
MailShadow for Google Apps (Beta 1) after installation will
cause modifications to existing items to NOT get synced to
Google, and vice versa.

Please put MailShadow for Google Apps (Beta 1) through its paces and send
us your comments, suggestions, and feedback at our Beta support site at:
http://www.cemaphore.com/gsupport.php

Thank you for agreeing to participate in our Beta Program!

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MailShadow for Google Apps (Beta 1) User Guide and Known Issues List

Uninstalling MailShadow for


Google Apps (Beta 1)
1. To Uninstall MailShadow for Google Apps (Beta 1), go to All programs /
Cemaphore /Uninstall MailShadow For Google Apps.

John Smith

2. At the end of the un-installation process, the uninstaller will prompt


you on whether you want to run a data clean-up utility as part of the
un-installation. We recommend that you run this utility and then
manually delete items in your test Outlook mailbox and test Gmail
mailbox.

3. If you don’t see the data clean-up utility dialogue box, press Alt-Tab
to bring it to the front.

4. Selecting Yes and running the data clean-up utility will execute a batch
data cleansing job against the Exchange mailbox and clean out hidden
properties in email, contacts, and calendar items that were placed
there by MailShadow for Google Apps (Beta 1) as part of its syncing
process. It will NOT actually delete the items themselves that are in
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MailShadow for Google Apps (Beta 1) User Guide and Known Issues List

the mailbox – that has to be done manually within Outlook (on the
Exchange side) and the Gmail web client (on the Google side) after the
product is uninstalled and you’ve run the data clean-up utility, and
we STRONGLY recommend you perform that operation.

Note: If you run the data clean-up utility but do not manually
delete the items on the Google side (using a web browser),
then re-installation of MailShadow will result in syncing
duplicate items into Outlook and Gmail.

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MailShadow for Google Apps (Beta 1) User Guide and Known Issues List

Detailed Known Issues List


The following are known issues with MailShadow for Google Apps Beta 1 as of
the date of its release.

Issue Summary Issue Details

1. Contact Activities, Contacts have data in the Activities, Certificates, and All
Certificates, and All Fields pages. These are not synced.
Fields pages are not
stored (5026)

2. Cannot delete meeting Quite often Outlook is unable to delete a meeting request
request in Outlook when accepting a meeting. Dialog comes up indicating
(5063) that the message cannot be deleted possibly because it
has been moved or deleted.

3. Contacts: "Other" field In Google contacts there are properties known as "Other
is not implemented in Fields". They contain the following fields (Home, Work,
Google (5028) Custom). The Google API does not support these.

4. Duplicate email when A task was created and then forwarded to a user. The task
forwarding a task contains a start and finish date with some subject info and
(5090) a text body in the email. When the task arrives in the
inbox in gmail, it looks like a single item, but inspecting
the item, it really is three items all the same.

5. Email synchronized When you generate email messages and verify that they
previously does not synchronize to Gmail then uninstall & reinstall, the items
sync after a re-install previously synchronized do not sync to Gmail.
(4991) Resolution: At end of uninstall process; choose option to
cleanse data on Outlook account.

6. Google labels and Having Google labels will create a corresponding folder
associated Outlook under the Outlook Inbox. If you delete the folder from
folders do not delete either side (Google side or Outlook side) it does not stay
(5078) deleted, but will reappear on the next sync cycle.
Cause:
Sync cycle brings it back
Resolution:
Delete both folders quickly (before the next sync cycle).

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MailShadow for Google Apps (Beta 1) User Guide and Known Issues List

Issue Summary Issue Details


7. Calendar Notifications Calendar notifications are sent randomly from Gmail,
Forwarded which can't be stopped easily or tracked down as to which
Unexpectedly (5061) email/user sent the message.
Cause:
This is default Google behavior – notifications are, by
default, sent to meeting attendees on Google Calendar.
Resolution:
Turn off all Google Calendar notifications and reminders in
your Google calendar, and all reminders on individual
meetings in Google Calendar.

8. Manually "hard" Executing a hard delete for contacts, email, or calendar


deleting large items will hang Outlook until the delete completes on the
numbers of items Google side.
(contacts, emails,
calendars can hang Resolution: Try deleting items in smaller batches.
Outlook (4937)
9. Missing email in GMail If MailShadow for Google Apps isn't running, changes to
if MailShadow not existing items that occur (e.g., via Outlook Web Access,
running via Gmail web interface, et.c) will not be reflected in
GMail.
Resolution:
Make sure MailShadow is running while changes are being
made.

10. Not all Outlook Some recurring events are not accepted by the Google
Calendar Dates are server (e.g., last workday of a given month).
Accepted in Google
Calendar (4900)

11. Outlook On-Line Mode MailShadow for Google Apps will miss changes made
Not Supported (5003) during if in on-line mode in Outlook.
Resolution:
Run in cached Exchange mode only in Outlook.

12. Cancelled A cancelled appointment is sycned from Outlook to Google


Appointment in but not under its own calendar, but under a calendar
Google under different called Http://schemas.google.com/g/2005#event.
Calendar (5112)
13. Sent Items Synced to This is a result of the way Google displays IMAP-synched
Gmail "Sent Mail" items in its web mail interface. Click on email item to see
Folder All Show "To: original recipients.
Me" (5122)

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MailShadow for Google Apps (Beta 1) User Guide and Known Issues List

Issue Summary Issue Details


14. Some fields from the The following fields do not get synced to Google Contacts:
Outlook Contact Title
Details page do not
get synced from Suffix
Outlook to Google Birthday
(5025) Anniversary
Internet Free-Busy (URL)

15. Splash Screen taskbar During startup the MailShadow splash screen causes a
windows has no blank Outlook taskbar item to appear.
header/Title (5046)

16. Outlook subfolders Subfolders under the Outlook Inbox are mapped to
under Inbox don't get “Gmail” label on Gmail.
“Inbox” label on Gmail
(5085)

17. Two Contacts with the If two contacts in Outlook/Exchange for the same person
Same Primary Email have the same primary email address, but all other fields
Address in Outlook different, and you delete one of the entries, it causes the
only show as One in second one to get deleted as well.
Gmail (5146) Cause:
Google uses the primary email address as its UID.
Resolution:
Use different primary email addresses in the two contact
items.

18. Updates on the same Updates on the same Calendar item sometimes get old
Calendar item reminder information (e.g., add and remove several
sometimes get old reminders and you may query old reminder instance
reminder information information)
(4894)

19. Updating the When you perform an update in a reminder on the Google
Reminders in Google Calendar item, Google does not register it as a change.
Calender do not One must change one of the other fields as well (e.g.,
Register or Sync back location)
to Outlook (4893)

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MailShadow for Google Apps (Beta 1) User Guide and Known Issues List

Issue Summary Issue Details

20. Taking an existing Gmail contact retains the email address.


Outlook contact and
removing the email
address and saving it
with the field blank
does not sync over to
Gmail (5177)

Creating a message in Outlook and having it auto save to


21. Draft copies in Outlook the Draft Folder replicates to Gmail. When sending the
are synced but never message from Outlook, the draft is placed into the out box
cleared out of Gmail folder and a copy is saved in the sent folder. With Gmail,
(5174) the message stays in the drafts folder as if it was never
sent.

22. Outlook Rules are not


synced as Filters on
Gmail (5176)

23. Delivery notices, Read


Recipts, and meeting
response/acceptance
messages are not
synced from Outlook
to Gmail (5283, 5284,
5286) Plus (+), Ampersand (&), and other special characters that
have special meaning within a URL will cause login
24. Special characters in problems on the Google side for MailShadow for Google
Gmail account Apps.
password cause login Resolution: Don’t use URL-special characters.
failures for
MailShadow sync
(5201)

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