Why does Outlook keep "preparing [iCloud] calendar for first use"?

Hello all --
I just installed iCloud on my Windows 7 laptop and configured it to integrate with Exchange. The functionality seems to work but there are two very annoying behaviours that I hope someone can help me with:
Every time I switch to the calendar view I get a little bubble in the taskbar saying "preparing calendar for first use". This ends up freezing Outlook for about 45- 60 seconds -- long enough for the Outlook window to have a "(not responding)" added to the title bar. This freeze-out is massively disruptive. It seems like Outlook is re-preparing the new iCloud calendars every time. Is this normal? Is there a configuration setting I could look at for this?
The iCloud calendars are always checked when I start up. Is there any way to uncheck them? Solving this might solve #1 above
Any suggestions on how to resolve and/or debug these further?
Thanks!
Ramon

Hi Ramon,
I have submitted a bug report before but haven't heard anything yet. Read more about it over here...
https://discussions.apple.com/message/17820467#17820467
Thanks,
Thomas

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Any solution for iCloud - Outlook integration - Preparing calendar for first use?

Every time I switch to the calendar view I get a little bubble in the taskbar saying "preparing calendar for first use". This ends up freezing Outlook for about 45- 60 seconds -- long enough for the Outlook window to have a "(not responding)" added to the title bar. This freeze-out is massively disruptive. It seems like Outlook is re-preparing the new iCloud calendars every time. Is this normal? Is there a configuration setting I could look at for this?
Same/Reference issue found: ID # 10407486

I had the same issue, this is the solution that worked for me.
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-open outlook
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-delete icloud data file
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We have seen our community members ask questions about Outlook keeps prompting for credentials many times. This issue could be caused by numerous reasons. Below is a list of the most common reasons for this problem:
Outlook is configured to prompt you for credentials
Incorrect password cached in credential storage
Required Authentication Settings for outgoing server and incoming server
Outlook Anywhere is not configured to use NTLM Authentication
Corrupt Outlook profile
Slow or unstable network connection
Antivirus programs
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Outlook is configured to prompt you for credentials
If you are using an Exchange account, there is a setting in your Outlook profile to always prompt for logon credentials. To find the setting, please follow:
1. In Outlook 213, go to File tab > Info >
Account Settings > Account Settings…
2. Highlight your Exchange account and click Change button.
3. Click on More Settings button.
4. Select the Security tab.
5. Under the User Identification, make sure the “Always prompt for logon credentials” option is not selected.
If you are using other types of email, please make sure you have ticked the option “Remember password”.
Incorrect credential cached in Credential Manager
Your Windows system stores user credentials on your computer. If the cached credentials are incorrect, you will be prompted for password. This issue usually happens after the password for your domain user account is changed. Before your password changed,
you saved your credentials. The stored credentials are not overwritten when Outlook triggers the authentication prompt even if you enable the Remember my credentials option.
To fix this issue, you need to remove the corrupted credentials, follow these steps:
Click Start, click Control Panel, and then click Credential Manager.
Note If View by is set to Category, click User Accounts first, and then click Credential Manager.
Locate the set of credentials that has Outlook in the name.
Click the name to expand the set of credentials, and then click Remove from Vault.
Repeat step 3 for any additional sets of credentials that have the word Outlook in the name.
Required Authentication Settings for outgoing server and incoming server
Different email provider may need different authentication settings. Please make sure you have set the server settings correctly. You can contact your email provider to gather the information.
In general, we select the “My outgoing server (SMTP) requires authentication” option and the first bullet “Use same settings as my incoming mail server”.
In addition, click on the Advanced tab and check if you have enter the correct Server Port Number and select the correct encrypt type. Below is a screenshot for an IMAP account:
Outlook Anywhere is not configured to use NTLM Authentication
The Outlook Anywhere feature allows you to access your Exchange account remotely from the Internet when you are working outside your organization's firewall.
When using Outlook Anywhere to connect to your Exchange server, we need to choose
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the password is sent in clear text. Using NTLM Authenticationcan significantly reduce the number of password prompts.
To check the authentication setting, please go to File > Account Settings > Account Settings,
select the Exchange account, and then click
Change. In the Change Account wizard, click
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Slow or unstable network connection
If your network connection is slow or unstable, Outlook may lose connection to the mail server. When Outlook try to reconnect, it will prompt for the credentials. To verify this, please switch to a stable network environment and then check if this issue
persists.
Corrupt Outlook Profile
Corrupt profile may cause Outlook to no longer remember your password. Please try to create a new mail profile in Control Panel and reconfigure your email account in the new profile to fix the issue. To create a new mail profile, you can refer:
http://support.microsoft.com/kb/829918
Antivirus software
Antivirus software usually integrates into your Outlook and it may cause some conflicts. Try to temporarily turn off your antivirus software to check if the issue will be gone.
Shared Calendar
Shared calendars can impact the user credentials, this issue may also occur if you have shared calendars opened in Outlook. You can try to unselect the shared calendar to check the result. It’s recommended to not open the shared calendar unless you want
to view them.
If you have any comments, welcome to post in the forum. Thank you.
Please click to vote if the post helps you. This can be beneficial to other community members reading the thread.

Nope...
I went through point by point by point, top to bottom, checking and verifying every single item as a possible cause for why my system (Outlook 2013 running on Windows 8.1 and connecting to Exchange 2010) insists on prompting me for my password every single
time I start Outlook. None of the solutions worked, my system still prompts me. I don't even have to supply a password. When the prompt dialog appears, I just cancel it. Within a few seconds, the bottom Outlook status bar changes to
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Why does Outlook keep "preparing [iCloud] calendar for first use"?

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