Please note, there are two completely different solutions to this issue. If the first does not address your instance of the issue, please also try the second. Both are listed below.
The first and most common reason that the OfficeCalendar icons do not reappear is that Outlook did not properly close when last exited. This is no fault of yours and is actually quite common with Outlook, especially if you are using any type of Palm or handheld device. Since the OfficeCalendar icons are generated dynamically when Outlook starts, if Outlook stays open in memory, a "fresh" start is never achieved and Outlook never notifies OfficeCalendar to run the startup process. To verify and correct this behavior follow the steps outlined below:
1. Exit Outlook as you would normally.
2. Press Ctrl+Alt+Delete once. This will launch your Windows Task Manager
3. Within Windows Task Manager, click the second tab labeled Processes.
4. Click the Image Name column heading to sort the list of running processes alphabetically.
5. Scan the list of processes for OUTLOOK.EXE, and if present, highlight it and choose End Process. If OUTLOOK.EXE is not present, skip to #8.
6. Choose Yes that you want to end the process if prompted.
7. Once the OUTLOOK.EXE process is ended exit the Task Manager.
8. Restart Outlook. The OfficeCalendar icons should now be present.
Outlook can stay open in memory for many reasons. If you are syncing with a Palm, PocketPC, cell phone, etc, the syncing program will hold Outlook open in the background so it can communicate with your data. Also, certain versions of Outlook (most notably Outlook 2000) seem to not shut down properly by design. They can stay open and check mail for you in the background. If this is a problem with your installation, then you can search for utilities on the Internet that will force Outlook to close when you close the interface. OfficeCalendar does not endorse any specific utility. Also, beware that having Outlook open in the background may be necessary for some other applications, like any that synchronize with an external device.
The second reason why the OfficeCalendar icons may have disappeared is that Outlook has disabled the OfficeCalendar application. If the above process was not successful at bringing the icons back, please proceed to the steps below.
1. Within Outlook, click "Help", then "About Microsoft Outlook".
2. Look for a button on the lower right labeled "Disabled Items".
3. If present, click "Disabled Items" and a new dialogue box will appear.
4. Scan the list of disabled items for "OfficeCalendar" or anything containing a "mscoree.dll", and if present, highlight it and choose "Enable".
5. Save changes and then close the dialogue box, exit Outlook, and restart Outlook.
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