Yes, I would track using the Message ID of the message
Example:
$Servers = Get-ExchangeServer; $Servers | where {$.isHubTransportServer -eq $true -or $.isMailboxServer -eq $true} | Get-MessageTrackingLog -MessageId ba18339e-8151-4ff3-aeea-
******@mailbox01.contoso.com | Select-Object Timestamp,ServerHostname,ClientHostname,Source,EventId,Recipients | Sort-Object -Property Timestamp
Look for any FAIL events.
Or filter for them:
Example
$Servers = Get-ExchangeServer; $Servers | where {$.isHubTransportServer -eq $true -or $.isMailboxServer -eq $true} | Get-MessageTrackingLog -MessageId ba18339e-8151-4ff3-aeea-
******@mailbox01.contoso.com -EventId Fail