Google Apps and
Microsoft Exchange EMail
Client Comaprison
Items of evaluation
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MTA’s (Message
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Transfer Agent)
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The Internet
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Language Support 
Mailbox Size
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Use of Outlook
POP, IMAP
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Availability
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Web Mail Clients
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Folders VS Labels
Threaded Mail View
Archiving
Searching
Filtering and Rules
Forwarding
Spam, Junk Mail
Offline/Cached
mode
Shared Mailboxes
User Passwords
Public Folders
MTA’s (Message Transfer Agent)
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Both systems do a fine job moving
message from one mailbox to another. So
long as the message is properly
addressed it will make it. There are some
differences though.
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Message Size
Rules
Email Domains
Services Sending Email
Logging
MTA: Message Size
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With Exchange we have a 100MB email
size limit. This option is configurable by
Middlebury’s system administrators.
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With Google there is a 20MB email size
limit. This is set by Google and we cannot
change it.
MTA: Rules
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With exchange we have the ability to deploy MTA
rules. To date we have only used this feature to
control e-mail outbreaks.
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With Google Apps MTA rules are handled with Postini
services for Google apps. These services are pretty
close in functionality to those provided by Exchange.
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MTA Rules allow:
1.
2.
3.
4.
5.
6.
Email content policies for sensitive or confidential information
Email attachment policies to quarantine or block specific file
types
Email footers for all outbound messages
Encryption using standard TLS protocols
Additional layer of spam and virus protection
User account synchronization with Google Apps Premier
Edition
MTA: Email Domains
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With Exchange, we support many different Email domains. Technically this means attaching
multiple e-mail addresses to a single mailbox.
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Google will allow us to attach multiple e-mail
addresses to a single Google app domain.
◦ Currently Middlebury Provides pro bono e-mail services
to some local not for profit organizations like Isley public
library and the united way of Addison county.
◦ According to Google, non-profit organizations with under
3,000 users qualify for their free Education Edition,
allowing these organizations to use their own Google
Apps for free.
MTA: Services Other servers
Sending Email
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We have multiple servers on campus that send email. Currently these send e-mail directly to our
mail servers.
◦ Banner, Hyperion and FNIS are examples of this.
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In a Google apps environment, we would need to
add a mail server to relay that e-mail to Google.
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The only major difference in how the user will
see this is the service e-mails would go through
the SPAM filtering. Currently this e-mail is routed
around our spam firewall preventing any chance
that a banner report that is e-mail to someone
will be killed as SPAM.
MTA: Logging
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With exchange I have access to message logs
that go back approx. two weeks and spam logs
that go back about 2 months.
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With Google Apps, we access to the
administrator audit API that provides similar
functionality. (Without the spam logs). Albeit
only accessible to someone who can program.
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This becomes important when we need to answer
questions like “did student x really send to e-mail
to me at this time and get rejected?”
The Internet
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Exchange will still be available to on-campus
users if the internet is offline. It is true that
internet outages are rare, but we have has ice
storms around here that have taken power and
communications down for a week at a time. Yes,
Exchange will need power, but that is the first
priority to be restored, phone second, all others
third.
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Google email would be unavailable from the
campus network until our internet feed could be
restored. That said, campus-wide internet
outages would not affect GMail access to users
with alternate internet connections (such as from
home, via cellular networks, or from Monterey).
Language Support
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Both exchange and Google offer an
impressive, and nearly identical, set of
languages.
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Both offer left to right capabilities.
Mailbox Size
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Currently our mailbox quota is
 2GB (1GB for students) Issue Warning
 3GB (2GB for students) Prohibit Send
 4GB (3GB for students) Prohibit Send and Receive.
◦ This can be change at a user request.
◦ The maximum size and exchange mailbox is technically 2TB
(2048 GB), but realistically about 15GB.
◦ And even more relevant, how much storage do we have to
give to the e-mail service.
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The offered mailbox size for Google app is currently
7491 MB (7.491647 gigabytes).
◦ Google slowly increases mailbox size as time goes by.
◦ The Premier Edition of Google Apps would have to be
purchased for all users at $30/user/year to upgrade to
25MB of storage for each mailbox.
Use of Outlook
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The primary client staff and faculty PC users use
with our Exchange e-mail system is Outlook.
◦ We currently have Outlook 2003 and 2007 deployed
across campus.
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Outlook is not widely used by students
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The primary interface for Google Apps email is
the web interface. Outlook can continue to be
used with addition of an Outlook plugin.
◦ When using the plugin most features are available
through Outlook, though for some things (e.g. creating
mail filters or configuring forwarding) users will still need
to use the GMail web interface.
POP, IMAP Availability
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Pop and IMAP are available as client
options for both systems.
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POP and IMAP are available by default on
exchange.
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On Google Apps POP is available by
default, but IMAP needs to be turned on
by the user in their Mail settings.
Web Mail Clients
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The web client is Google’s bread and butter.
It is the most full featured client available for
Google Apps and provides an experience that
is on-par with any desktop application.
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Currently the supported browsers are:
http://mail.google.com/support/bin/answer.p
y?hl=en&answer=6557
◦ Google Chrome (Windows Mac Linux)
◦ Firefox 2.0+ (Windows Mac Linux)
◦ Internet Explorer 6.0+ (We recommend Internet
Explorer 7.0+ for the best experience, and you'll
need it to use Gmail labs and Themes.)
◦ Safari 3.0+ (Mac)
Web Mail Clients
cont.
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The webmail client for exchange was completely rewritten for Exchange 2010.
The full version of the client, in Exchange 2007, was only available to PC users
using Internet explorer. For everyone else it was the “Light” client, which was a
very basic client. It was not suitable for everyday use. In Exchange 2010, the
web client now works across many different browsers and almost duplicates all
of the functionality found in Outlook 2010.
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Microsoft Exchange Server 2010 supports the following browsers.
http://technet.microsoft.com/en-us/library/dd351200.aspx
◦ On a computer running Windows XP, Windows Server 2003, Windows Server 2008,
Windows Vista, or Windows 7, you can use:
 Internet Explorer 7 and later versions.
 Firefox 3.0.1 and later versions.
 Chrome and later versions.
◦ On a computer running Mac OS X, you can use:
 Safari 3.1 and later versions.
 Firefox 3.0.1 and later versions.
◦ On a computer running Linux, you can use:
 Firefox 3.0.1 and later versions.
Folders VS Labels
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Folders in Exchange are just like folder in the file system. There is a hierarchy
and items live in one of these folders. If you want it to be in two places, you
need to copy it. Exchange also supports categories for organization, but very
few people use this feature.
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In Google Apps, you place a label on an e-mail. Messages can have as many
labels as desired, allowing a message to be included in multiple groups without
being duplicated. Labels are listed in the sidebar of the GMail web-client, each
providing a view of all messages with the chosen tag. If you use the GMail
plug-in for Outlook, it actually duplicates the “Folders” you see in Outlook as
labels in Google Apps.
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In GMail, labels apply to conversations rather than individual messages. This
means that once a conversation (even one with just a single message) has
been labeled, all replies take on that label as well.
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Most people who have gone through this type of conversion say that Labels are
at first thought to be a major problem, but quickly they become a non-issue.
Threaded Mail View
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Google Apps always shows e-mail messages
organized into “conversations,” grouping all replies
together. As new replies to a message are received,
its conversation comes to the top of the inbox and the
new replies are shown expanded while the older parts
of the conversation are collapsed. The messagehistory included with each message is collapsed by
default, keeping long back-and-forth email chains
easy to read.
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Outlook 2010 and the Exchange web client for 2010 a
threaded conversation filter that can be turned on
and off. The message-history included with each
message is always shown causing messages with
many replies to become very long.
Archiving
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One workflow difference between Google Mail and
Exchange is the process of archiving messages.
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In Exchange/Outlook if you want a message out of your
inbox but don’t wish to delete it, you must move it to
another folder. When a reply to the message is received, it
will appear in your Inbox and then must be copied to the
same folder after being read.
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In Google Mail, the “Inbox” is simply a label that is
automatically applied to new mail. There is a button on the
toolbar called “Archive” that removes the “Inbox” label
from mail while leaving it available in the “All Mail” view. If
additional labels are applied to a conversation these will
remain on the conversation even as new replies are
received, allowing the reply to be read in the inbox and
then archived with a single click to the “Archive” button
Searching
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Google is a searching company first and
foremost. So Google apps does this very well
and with the responsiveness that you would
expect from Google.
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With exchange 2007 (our previous version)
searching was a slow process that didn’t
always get you what you wanted, but with
exchange 2010, the responsiveness is there.
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Google’s interface is more intuitive, but both
will find the message you want.
Filtering and Rules
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Filtering and Rules
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Exchange calls this rules and Google calls this filtering. But they
are the same thing. These offer a simple way to apply some
predefined rules to incoming e-mail and perform some simple
actions.
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Both systems offer the basic set of commands, like delete the
message or move it to a folder (label it in googleze).
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Exchange does allow for more complex rules, like automatically
replying to a specific person with a specific message and the
important, stop processing after this rule option.
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Exchange also allow for some rules like pop up a message when
this person send me e-mail. This is a client-side rule. It only rules
when the client is attached to the server, because it is using some
features of Outlook to perform this.
Forwarding
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In Google Apps, the forwarding is done in the
settings/forwarding config page. It will not let
you forward to any address that is part of the
Google apps environment. It has to be an
address at another domain (Not
@middlebury.edu, or @miis.edu)
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Which exchange there are two ways to do this.
1.
2.
Make a rule to fire on all incoming e-mail and tell it to
redirect it to another address. (It can be any address)
Use Middlebury’s own forward tool that will forward all
e-mail to another server (and not leave a copy behind
it the mailbox.) Won’t let you choose an
@middlebury.edu address.
Spam, Junk Mail
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Spam filtering for Google is handled by Google. Google tags
incoming e-mail as spam and routes it to your SPAM folder.
Message in you SPAM folder are automatically deleted after 30
days.
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Spam in our exchange system in handled by 3 Barracuda SPAM
firewalls. All incoming e-mails come in to two firewalls and are
given a spam score from 0 (not SPAM) to 10 or higher (10 is no
way it isn’t spam). The higher the score, the greater the likely
hood of spam. Messages that are below a score of 3.5 are sent in
on to the mailbox. 3.5 to 7 then messages are tagged in the
subject like with [SPAM?] and 7 and higher are dropped as spam.
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Our current arrangement allows someone to log into the spam
filters and modify their settings to what they want and modify
white and black lists.
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We also have one SPAM firewall that checks all of our outgoing emails as well.
Offline/Cached mode
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Offline mode (Google) and cached mode (Outlook) are ways of accessing you
e-mail when you are not on the internet. Entourage runs in cached-mode the
same way as Outlook, though unlike outlook, cached-mode can’t be disabled.
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Cached mode works by copping all of your exchange information into a local
file on your computer. This is default for outlook 2007 and 2010. In cached
mode, if you are online it will connect to the exchange server and you can get
and send updates.
1.
2.
3.
4.
5.
New e-mails
status changes of messages (Unread/read)
Deleted e-mail
Calendar changes
Ect…
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When you are not online, it will allow you to work with your local copy of the email, but you won’t receive new updates and can’t send e-mail.
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In addition to being able to use cached-mode in an IMAP client (such as
Outlook) to access GMail, the GMail web-client uses a system called “Google
Gears” to store the most recent portion of your email in a database resident in
your browser. When no internet connection is available Gmail continues to
operate with data cached via Gears and then syncs incoming and outgoing
messages automatically when an internet connection is restored.
Shared mailboxes/Delegation
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With exchange we have the ability to assign multiple
users access to the same mailbox. You log in as
yourself, but have access to multiple mailboxes as the
same time.
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With Google there is an option called mail delegation.
This allows multiple users access to the same mailbox
at the same time.
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HOWEVER this is only available with Google Apps
Premier Edition. This is Google’s top of the line paid
e-mail service at $30 per person per year.
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Assuming that we go with the education edition, you
will need to log off as yourself and then log on as the
other user to gain access to another mailbox.
User Passwords
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Google Apps is it own thing, so it has a whole
new set of accounts for users. We will make
accounts with the same username as your
current username.
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But…
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Depending on some choices, we may have all
users have a new password to remember. We
may alternatively integrate Google Apps
authentication with CAS (our unified web based
authentication system), which will link to your
current MIDD account and keep passwords
storage and validation on-campus.
Public Folders
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The most common thing we do with public folders in
Exchange is to share calendars. This is useful when you
want a shared calendar, but not have a mailbox to manage.
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Google apps does not have public folders, however
calendars can be shared with multiple users with each user
having one of four permission settings on the calendar:
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See only free/busy (hide details)
See all event details
Make changes to events
Make changes AND manage sharing
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These granular permissions on individual calendars remove
the need to use public folders for calendar sharing.
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There are some places where e-mail is shared in a public
folder. In Google Apps this would be replaced with a
distribution group and some discipline.