question

Hi @KarlRolfe-7045
In this case, you could create more items and attach the same document to these items at the same time, the result is like this:

Every item is for one new employee.

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Hi @KarlRolfe-7045
If you want to save only one item in your list, you could use Power Automate to achieve your goal:

In my case, I get the attach file from my site, you could choose different path as you want. As a result, once we delete the item in this list, it will create a new item with the attachment automatically.

What's more, the item could also be deleted automatically, just login M365 admin center > Data lifecycle management, create a label and set the retention time as you want (for example I select 7 days):

As a result, the item will be deleted 7 days later, at the same time, a new item with attachment will be created automatically.

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Hi @KarlRolfe-7045
If there are several documnets you need to attach on each item, you could try to complete it using powershell, in this method you could save time. The code shown below is about adding multiple attachments to the list item, before running it we need to add all files from a given folder to SharePoint Online.

 #Set Variables
 $SiteURL = "https://crescent.sharepoint.com/sites/pmo"
 $ListName = "Projects"
 $ItemID ="2"
 $FolderPath = "C:\Temp\Docs"
     
 #Connect to PnP Online
 Connect-PnPOnline -Url $SiteURL -Interactive
     
 #Get the List Item
 $ListItem  = Get-PnPListItem -List $ListName -Id $ItemID
     
 #Function to Add all files as a attachment to list item
 Function Add-AttachmentsFromFolder($ListItem, $FolderPath)
 {
     #Get All existing attachments from list item
     $AttachmentFiles = Get-PnPProperty -ClientObject $ListItem -Property "AttachmentFiles"
     
     #Get the File and Add to List Item Attachment
     ForEach ($File in  (Get-ChildItem $FolderPath -File))
     {
         $AttachmentFile = $AttachmentFiles | Where { ($_.FileName -eq $File.Name) }
         If($AttachmentFile -eq $Null)
         {
             $AttachmentInfo = New-Object -TypeName Microsoft.SharePoint.Client.AttachmentCreationInformation
             $AttachmentInfo.FileName =  $File.Name
             $AttachmentInfo.ContentStream = $File.OpenRead()
             $AttchedFile = $ListItem.AttachmentFiles.Add($AttachmentInfo)
             Invoke-PnPQuery
             Write-host -f Green "Added Attachment File:"$File.FullName
         }
         Else
         {
             write-host -f Yellow "Attachment '$($File.Name)' Exists already!"
         }
     }
 }
 #Call the function to add all attachments from folder
 Add-AttachmentsFromFolder $ListItem $FolderPath

Note: you need to change the parameter as you need.

As the characters exceed the count allowed in comment, I convert the comment to an answer.

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