Outlook Connection States
Outlook 2003 regularly transitions between a number of different connection including
connected, disconnected and offline. This document will endeavor to document these
conditions, explain how these conditions are entered and how they can be exited, and
explain how to determine which of the connection states Outlook is in at any given time.
The Connected State
You can send and receive email in the connected state. When Outlook 2003 is running
on a Windows XP machine with a valid connection to the Internet, Outlook should be in
a connected state. Being in the connected state means that an authenticated connection
has been made to the Exchange Server and that connection is currently available for use.
This is the normal state of Outlook 2003.
The current state of Outlook 2003 is always displayed in the lower right corner of the
Outlook 2003 main window. When in a connected state, Outlook will typically display
the following:

When Outlook shows this, you can be assured that everything is in working order.
The Disconnected State
You cannot send and receive email in the connected state. Through information provided
by the operating system, Outlook 2003 is aware of network connectivity. For instance, if
Office 2003 is in a connected state and the network cable is suddenly disconnected, the
operating system will realize this and will inform Outlook 2003. At that point, Outlook
2003 will enter a disconnected state. Outlook 2003 only enters a disconnected state when
Outlook cannot contact the Exchange Servers as expected. Usually, this happens when a
network cable is unplugged, when there are network issues between the client and server,
or when the server is actually down.
When your Outlook 2003 application enters the disconnected state, you will see this
status represented in the bottom right corner of the main Outlook window, as shown
below:

Notice that a “last updated” time is displayed as well. This last updated time can give
You some indication of when Outlook went into a disconnected state.
It should be noted that even when Outlook 2003 is in the disconnected state, it is able to
automatically reconnect to the Exchange server as soon as network connectivity is
restored.
Trying to Connect…
When network connectivity is restored to a computer where Outlook 2003 is in the
disconnected state, Outlook 2003 will begin to reestablish a connection to the Exchange
server. While doing this, Outlook will present the user with a variety of messages as
detailed below.
First, Outlook will begin “Trying to connect…”. These are the first steps in the
connection process. You will notice that the “last updated” time is still presented here
because that folder has still not been updated and no connection exists as of yet.

Next, Outlook will present a “Waiting to update this folder” message alongside the
“Trying to connect…” message. This means that some of the connections have been
made to the Exchange server, and a request for an update of the currently displayed folder
has been sent.

Next, Outlook 2003 will go into a connected state. When we reach this point, Outlook
has established the required network connections, and data will begin to be exchanged
Between the client and the server.

Next, messages and any associated attachments are transferred between Exchange and
Outlook 2003. Sometimes, when there is a significant amount of information to be
transferred, you might see a message indicating how much information is being
transferred between the server and the client. You might also see information about other
folders being updated as well. This is generally seen on a first synchronization, or when
you have received a significant number of emails into a folder between connections to the
server.
After all folders have been updated completely, you finally get to the connected state as
discussed above. In this state, Outlook 2003 is just waiting to send or receive email.
This should be the most common state for Outlook 2003.

The Offline State
You cannot send and receive email in the connected state. The offline state is a state
where Outlook has disconnected from the Exchange server computer. Outlook will not
automatically try to restore that connection. When you are in an offline state, email will
not be sent or received, even if a network connection is available and functioning
properly.
There are various indicators to show when Outlook has entered the offline state. For
instance, if we look back to the bottom right corner of the Outlook 2003 main window,
we will see something similar to the following:

This shows that Outlook is in an Offline state, and as with the disconnected state
described above, we have a “last updated” message that might indicate when we were last
in a connected state with our Exchange Server computer.
There are a couple of other indicators for the offline state. If you click once on the
“offline” icon in the lower right corner and you see that a context sensitive menu pops up
and it shows that “Work Offline” has a checkmark next to it.

In addition to that context sensitive menu, the main File menu in the upper left corner of
the main Outlook 2003 window will show us whether Outlook 2003 is in an offline state.
As shown below, near the bottom of the menu, there will be a checkmark next to the
“Work Offline” menu choice.

How Did I Get Into The Offline State and How Do I Get Back Online?
Outlook goes offline through user intervention. Outlook should not enter an offline state
automatically. Outlook 2003 will typically switch between connected and disconnected
automatically as shown above, but those are the only “automatic” state changes that it
should make.
With that said, there are a few things that a person could do to put Outlook 2003 into an
offline state without intentionally doing so. Each time you log in to Outlook 2003, when
Outlook is making the initial connection to Exchange, you will be queried for credentials.
It should be noted that you will be challenged in this manner each time you start Outlook,
and you must enter your credentials each time you start the Outlook 2003 application or
are otherwise prompted.
When this challenge happens, you will be presented with a window similar to the
following:

When this dialog box is presented, if you choose to “Cancel” rather than enter their
credentials, Outlook will be opened in an offline state. Since you are already
authenticated to the local machine, you have access to the offline store that Outlook 2003
uses when in cached mode even if you do not authenticate. The cached Outlook files will
be opened, and your mailbox will be presented as it was the last time an authenticated
connection was made. (You have access to your mailbox because this is a file on the
local file system, and you have access to that file when you log on to your computer.)
Instead of cancelling, if you type your credentials incorrectly, you will not be
authenticated. The easiest way to check that you are authenticated is to click the
“Send/Receive” button. 
If you have accidentally mistyped your name or password, you will be prompted to reenter
your user name and password in the authentication window pictured above.
Remember that your user name is in the format of Center\firstinitial+last name such as:
Hq\jdoe Also, remember that your password is case sensitive. Check the Caps lock key
on your keyboard to be sure that it is not on.
A second way that you could put Outlook into an offline state is to change either of the
two menus where we checked the offline status earlier. On either the file menu as below:
…or on the context sensitive menu from the bottom right of the Outlook main window, as
shown below:


By selecting (putting a checkmark in front of) “Work Offline” on either of these menus,
you can force Outlook into an offline state. By deselecting (removing the checkmark in
front of) “Work Offline” you can force Outlook to work online.
Once you remove the check in front of “Work Offline,” the easiest way to verify that you
are authenticated and working online is to click the “Send/Receive” button.

You should be aware of the fact that when you exit the offline state, you may be
challenged for credentials. This just means that Outlook has been in an offline state since
it was started, and it has never had the credentials to pass on to the Exchange server for
access to your mailbox. As always, you must input these credentials when prompted, or
you will be left in an offline state.
If you were working offline and now wish to work online, you may be prompted to enter
your user name and password in the authentication window.
It should be noted that if Outlook is shut down in an offline state, when you start Outlook
again, Outlook will remain in an offline state. Outlook will stay in this state until you
bring Outlook into an online state by performing the steps described above.
Thanks to NASA Operations Messaging & Directory (NOMAD) for this beautiful guide