Looks like SCCM doesn't distribute packages already assigned to the collection when you add a DP to that collection's properties.
Quick and dirty script to do it
Get-CMDeployment -CollectionName "DEV-JC-TestUsers" | ` ForEach { Write-Host $_.packageId + " " + $_.ApplicationName Get-CMPackage -Fast -Id $_.packageID | Start-CMContentDistribution -DistributionPointGroupName 'DP Group1' } Get-CMDeployment -CollectionName "DEV-JC-TestUsers" | ` ForEach { Write-Host $_.packageId + " " + $_.ApplicationName Get-CMApplication -Fast -Name $_.ApplicationName | Start-CMContentDistribution -DistributionPointGroupName 'DP Group1' }