Our best practices come from customer feedback.  See the top tips below:

1. Ensure that Office 2003/2007 is fully patched and the OS you are running (either Windows Vista or XP) is fully patched. This really resolves a great number of problems.

2. The user account used for the installation of MailShadow Desktop Edition must have local administrator privileges on the machine. This is just for installation.

3. MailShadow Desktop Edition uses secure IMAP port 993 to synchronize email to Google Apps. If your organization does not permit port 993 outbound through the firewall, it will not work. Please contact your firewall administrator to open port 993 to imap.gmail.com.

4. If you are syncing between Exchange and Google Apps , please put the Exchange profile in the first (upper) mailbox position and configure the Google Apps account in the second (lower) mailbox position. This helps us help you if you need technical support.

5. If you occasionally see reminders popping up, please close Outlook and restart with this command line “C:\Program Files\Microsoft Office\Office11\Outlook.exe /cleanreminders” .  You need to do this only once.

6. The calendar feature on Google Apps has to be used at least once before you can sync Outlook contacts to Google Calendar.

7. If you need support, please send the logs from the time of the issue to support@cemaphore.com

On XP they are located in: C:\Documents and Settings\(logged on user)\Application Data\Cemaphore\MailShadowSync\Logs

On Vista they are located in: C:\Users\(logged on user)\AppData\Roaming\Cemaphore\MailShadowSync\Logs

8. Occasionally (especially with an Android phone),  we can send data so fast to Gmail that an account lockout can occur for Gmail or Calendars or Contacts or all three. Don’t worry, the Google Apps web interface will still work without issue. Depending on the conditions, MailShadow can be locked out for some amount of time. You can sometimes accelerate clearing the lockout by going to https://www.google.com/accounts/DisplayUnlockCaptcha.

9. If you are upgrading from a previous version of MailShadow for Google Apps, please uninstall MailShadow for Google Apps before installing MailShadow Desktop Edition and restart the computer. If  there is anything you want to delete in the accounts you are syncing , it would best to empty trash and do the deletes before starting the sync.

Tyrone Pike, CEO of Cemaphore Systems, was recently interviewed by Robert Scoble of Scobleizer TV.  Viewers participated in a live, interactive demo of the new MailShadow Server Edition solution which can sync and migrate 1000’s of mailboxes.   Watch how MailShadow enables on-premises and online Exchange users to co-exist and share resources—whether booking conference rooms or seeing free/busy sync on other calendars to simplify appointment scheduling.

As CTO for Cemaphore Systems, I frequently talk to customers about how to overcome the challenges of migrating from one version of Exchange to another.  We just announced MailShadow Server Edition that will allow you to synchronize/migrate your Exchange 2003 (or 2000) mailboxes to Exchange 2007 mailboxes cross-forest with little user downtime beyond 1) shutting down Outlook 2) creating a new Outlook profile to point to the Exch07 server, and 3) restarting Outlook against the Exchange 2007 mailbox.

Because it’s a bidirectional sync, you can in effect, pre-replicate all the Exchange 2003 mailbox data over to Exchange 2007 IN THE BACKGROUND while the users are still connected to Exchange 2003, then switch the Outlook/OWA users over at your/their leisure instead of forcing a knife-edge cutover for all users.  Also, the sync occurs continuously in real time, so if you have an on-premises Exchange server and a hosted Exchange service, you effectively get live backup of email data to the cloud.

MailShadow server syncs all your Exchange/Outlook folder data, email, contacts, calendar, Tasks, Notes types.

MailShadowG is a single user Outlook Add-in that installs in 5 minutes with message content protection commencing immediately.

It’s helpful to note that MailShadowG installs quickly and has a small footprint on the desktop. The install package is under 10 Mb and the RAM footprint is typically under 50Mbytes when running, with CPU consumption under 5 percent during normal operations (during the initial sync period, CPU consumption will be higher). The installer has just a few options for the user to configure, such as Google account credentials and alternate email send preferences. Once it’s installed, MailShadowG runs in the background with a System Tray icon for enabling/disabling the product. For IT departments, the .msi install package can be pushed out to corporate desktops via an AD group policy (or via other automated software distribution solutions.)

Both Outlook and Google have worked to develop a reputation for excelling in their industry: Outlook is known for it’s ubiquity in business as being “the” client for messaging and business critical information; Google is a search engine powerhouse online.

So, why not use the functionality of both to enable better business practices and simplify your life? You can with MailShadowG.

We’ve already mentioned the ability of using Outlook to compose offline e-mail messages for your Gmail account. But, what about searching for past messages – let alone threading messages in order to capture the entire online conversation?

True there is a search capability in Outlook to find e-mail, calendar and contacts; however, Google has focused on this niche for years, and they’ve made some pretty intuitive search tools.

Once you install MailShadowG, you now have the business functionality of Outlook and the search capability of Google at your fingertips. Then, the next time someone asks you for that e-mail with the business profile for XYZ Company, you’ll be able to search with ease.

A recent article in The Processor confirms a position we hold strongly: e-mail management – including archiving, server maintenance and upgrades and storage—is a necessary evil. Every company needs to meet this basic requirement—but the smaller the company, the more onerous the logistics of owning and maintaining an entire e-mail infrastructure of their own.


We love the insight Gartner analyst Matt Cain provides in this article:

“…That’s part of why Gartner predicts that email using a cloud approach will grow from 1% of the market, where it is today, to about 20% of the market by 2012, according to Matt Cain, research vice president at Gartner. Small companies, which have had the worst economics for premises-based email, will get the most out of moving their mailboxes into the cloud, Cain explains.”

The article quotes Cemaphore’s Tyrone Pike as well:

“’The fixed costs are much higher for SMEs because they are spreading it out over a limited, fixed number of seats,’ says Tyrone Pike, founder and chief executive officer of Cemaphore (www.cemaphore.com), a provider of email continuity and Exchange migration based on cloud email.”

The cost of staffing an Exchange expert in particular is one of the items that contributes most highly to infrastructure expenses. The need to have a geographically protected disaster recovery server, and to know that it is live and can be activated within the space of a few minutes is a cost consideration as well (although Cemaphore can handle that task quite gracefully with MailShadow v2.3.)


We fully support the Gartner findings that for SMEs – as well as for SMBs—the economic indicators are clearly pointed towards the economics and efficiency of moving an increasingly larger share of their e-mail continuity into the cloud.


What do you think? And is your organization ready for cloud-based e-mail? We welcome your comments. And we’ve included a link to the entire Sept. 5 Processor article. Click Here

MailShadowG enables safe, sound migration from Exchange to Google or Google to Exchange


Here’s another interesting tidbit about MailShadowG: it permits users to sync data from their Google account to Outlook/Exchange and vice versa, giving users the ultimate e-mail freedom of choice. Users can move between both worlds, run both environments concurrently, or can migrate from one to the other and back again, at will.


Because MailShadowG keeps both worlds continuously in sync for as long as it’s running, you no longer have to force your users to perform knife-edge cutovers between Exchange and Google, or between Google and Exchange. Yes, there are differences between the way each system stores and categorizes data, and differences in certain data types and fields. However, migration is much easier on the user and on the IT department with MailShadowG because it allows the user to get used to the differences at their own leisure.


For IT departments, running both concurrently for some period of time helps to avoid the myriad support calls from users who have yet to gain a personal understanding of the sometimes subtle differences in data and operation between their Outlook/Exchange and Gmail environments.

Studies typically estimate the cost of the average support call is $25, and that the average employee places about 5 helpdesk calls every year.

If MailShadowG can save even 1-2 of those calls, the product has paid for itself in support costs alone, let alone the access to increased storage and continuity and the reduced infrastructure expenditure involved. Now that’s a true bargain.

MailShadowG provides disconnected access to Gmail, Google Contacts and Google Calendar by caching Google content in Outlook for offline operations

Checking e-mail requires Internet access; writing e-mail doesn’t. Unfortunately, with web-based e-mail services you are severely limited in responding to e-mails – unless you want to write a bunch of word documents, then do a cut and past job once you get Internet access again. But how efficient is that, really?

On the other hand, Exchange-based e-mail coupled with the Outlook client gives you offline access to your e-mail, the ability to write e-mail and then store it in you outbox until your back online again. Wouldn’t it be nice to have the same functionality with a service like Gmail?

MailShadowG provides disconnected access to Gmail, Google Contacts and Google Calendar. MailShadowG acts as a third party that caches Google Apps content in Outlook for offline operations. This very literally removes the tether required to manage your Google content.

Now the same functionality you enjoy with an Outlook/Exchange setting can work with an Outlook/Google application.

MailShadowG maintains full e-mail continuity to Outlook even when Exchange is unavailable.


We’ve all experienced the frustration of losing Outlook connectivity because the Exchange server is unavailable, or has gone down. We’ve come to accept it as one of the frustrating facts of doing business.


Just one case in point – an event manager recently posted a notice about the death of an associate’s mother to all the associate’s team members on a Friday afternoon. Not noticing that Exchange was unavailable, she shut her computer and went home for the weekend. Her message remained in the outbox until the following Monday morning. The notice didn’t get to the team members until the funeral was over—too late for them to send their condolences or to try to attend. Unfortunately, this scenario is all too familiar – the business proposal, critical presentation or timely notice that has to be sent out through an alternative method, or even worse, sits in the Outbox unnoticed until the deadline has passed.


However, one of the really exciting aspects of MailShadowG is that it automatically detects Microsoft Exchange unavailability (as seen by the Outlook client) and offers users the ability to send outbound e-mail through their configured Gmail account as an alternative delivery option.


The user can configure how long to wait if Exchange is unavailable before sending queued items in the Outlook outbox through Gmail, or you can set the system up for immediate delivery through Gmail if Exchange isn’t there. The e-mail gets sent with your Gmail address in the “From” field and is moved to the Sent Items folder.


If the recipient responds, the response is delivered to the Gmail address and MailShadowG will also deliver it to the Outlook inbox, even if Exchange is still down. Imagine the possibilities! As long as the Internet is present, e-mail continuity continues, with or without a connection to Exchange.

Managing one address book is challenging enough, but keeping your contacts’ information in various locations only compounds the problem. And, it’s not likely you’ll have just work contacts in one and personal contacts in another. So, why not just merge all your contacts in one location?

Dennis O’Reilly made this suggestion in his regular Worker’s Edge column in Cnet News entitled “Merge your Outlook and Gmail contacts”. He’s spot on; managing your contacts from one location is far better than “Alt-Tabbing between… Gmail inbox and the Outlook account on [an] employer’s Exchange Server.”

This is one of the reasons why MailShadowG fully synchronizes your contacts. But that’s not all… By synchronizing e-mail, calendar and contacts between Gmail and Exchange, you can better mange your data from one location – Outlook.

Now, not only do you have your contacts in one location, you can edit contact information in one and have it immediately reflected on the other.