For the purposes of working offline in Outlook 2000, you need to follow some basic steps. Working offline is another way of saying working while not connected to the network. This is especially handy if you telecommute or travel with your laptop and you would like to compose some emails, while on an airplane for example. These emails can then be sent as soon as you connect to the company network via VPN. In a nutshell: simply boot up the laptop (be sure the battery is charged ), login to the network- even though you are not connected- and open Outlook 2000. Your Outlook must be configured to download the offline address book if you wish to email from with your Contacts listings. The alternative is to manually enter the email addresses from memory.
To configure Outlook 2000 to download the Address Book for offline use: before going offline, open Outlook 2000. Go to Tools/ Synchronize/ Offline Folder Settings. Under "Options" be sure the "Download offline address book" is checked. Hit apply. Offline Folders can also be selected as you want. Note that the default Outlook Folders cannot be unchecked (Inbox, Contacts, etc.).
The Settings tab to the right of the options can be reviewed as well.

Back to Working Offline using Outlook 2000, via Exchange Server 5.5:
Boot up the laptop. At the network login prompt, login as usual. Do NOT hit cancel.

You will see the following message, assuming there is not network connectivity. Click OK.

Open up Outlook 2000. After a few seconds, you will see the following message indicating that Exchange Server is not available. This makes sense because the laptop is disconnected from the network:

Select Work Offline and after a few seconds all Outlook 2000/Exchange folders slated for offline synchronization will appear.

Open up a new mail message.

The Exchange Server Offline Address Book should be available now. Click the To: button and you should have your selection of both the Offline Address Book and your personal Contacts [in the "Show Names from the" drop-down menu]. Choose the recipients from either list or manually enter an email, compose the message and click send. The message automatically goes to the Outbox folder in the folder list on the left. Cannot see this folder? Try going to View/Folder List. Double check to see that the email is there. Upon closing Outlook 2000, click yes to the message warning about remaining messages in your Outbox. Also, be aware that this email will be sent as soon as you next connect to the company network!
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