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Syncing SharePoint 2013 with Outlook 2013 is very simple! I can just click 'Connect to Outlook' in the ribbon and it's that easy: http://office.microsoft.com/en-ca/office365-sharepoint-online-small-business-help/synchronize-sharepoint-content-with-outlook-HA102774420.aspx

However besides my own, I want each user in my site collection to have their Outlook calendar in SharePoint. Is there a way to do this automatically or programatically? Can it be done with My Sites? Do I create a new Calendar list for each user and somehow sync with some code? If I sync every user's Outlook calendar into one list, that may get bloated as I have ~ 1000 users.

Any suggestions or direction is greatly appreciated.

1

At first, you must create My site to all users.

foreach($profile in $AllProfiles) 
{ 
    $AccountName = $profile[[Microsoft.Office.Server.UserProfiles.PropertyConstants]::AccountName].Value     
    Try 
    { 
        if($profile.PersonalSite -eq $Null) 
        { 
            write-host "Creating personel site for  $AccountName"  
            $profile.CreatePersonalSite()        
            write-host "Personal Site Admin has assigned"  
        } 
        else 
        { 
            Write-Warning "$AccountName already has personel site" 
        } 
    } 
    Catch 
    { 
        Write-Error "Failed to create personal site for '$AccountName'" 
    } 
}

After you can enumerate sites in My site collection and add calendar for each.

$spweb=get-spweb http://yoururl                             
$template = $spweb.ListTemplates["Calendar"]                        
$spweb.Lists.Add("My New Calendar", "New Calendar Description", $template)       
$calendarlist=$spweb.Lists["My New Calendar"]                                      
$calendarlist.Update()  

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