diff --git a/Admin/MonitorExchangeAuthCertificate/ConfigurationAction/New-ExchangeAuthCertificate.ps1 b/Admin/MonitorExchangeAuthCertificate/ConfigurationAction/New-ExchangeAuthCertificate.ps1
index 6adb3f7bf7..0396186cf5 100644
--- a/Admin/MonitorExchangeAuthCertificate/ConfigurationAction/New-ExchangeAuthCertificate.ps1
+++ b/Admin/MonitorExchangeAuthCertificate/ConfigurationAction/New-ExchangeAuthCertificate.ps1
@@ -120,7 +120,14 @@ function New-ExchangeAuthCertificate {
 
                                 if (($null -ne $internalTransportCertificate.Services) -and
                                     ($internalTransportCertificate.Services -ne 0)) {
-                                    $servicesToEnableList.AddRange(($internalTransportCertificate.Services).ToString().ToUpper().Split(",").Trim())
+                                    $transportCertificateServices = ($internalTransportCertificate.Services).ToString().ToUpper().Split(",").Trim()
+                                    if ($transportCertificateServices.Count -eq 1) {
+                                        # Use the Add() method if only one service is bound to the transport certificate
+                                        $servicesToEnableList.Add($transportCertificateServices)
+                                    } else {
+                                        # Use the AddRange() method otherwise
+                                        $servicesToEnableList.AddRange($transportCertificateServices)
+                                    }
 
                                     # Make sure to remove IIS from list if the certificate was not bound to Front End Website before
                                     if (($isInternalTransportBoundToIisFe -eq $false) -and
@@ -287,7 +294,13 @@ function New-ExchangeAuthCertificate {
                 try {
                     Write-Verbose ("[Required] Step 1: Set certificate: $($newAuthCertificateThumbprint) as the next Auth Certificate")
                     if ($PSCmdlet.ShouldProcess("Certificate: $newAuthCertificateThumbprint Date: $nextAuthCertificateActiveOn", "Set-AuthConfig")) {
-                        Set-AuthConfig -NewCertificateThumbprint $newAuthCertificateThumbprint -NewCertificateEffectiveDate $nextAuthCertificateActiveOn -Force -ErrorAction Stop
+                        $setAuthConfigParams = @{
+                            NewCertificateThumbprint    = $newAuthCertificateThumbprint
+                            NewCertificateEffectiveDate = if ($EnableDaysInFuture -eq 0) { Get-Date } else { $nextAuthCertificateActiveOn }
+                            Force                       = $true
+                            ErrorAction                 = "Stop"
+                        }
+                        Set-AuthConfig @setAuthConfigParams
                     }
 
                     if ($EnableDaysInFuture -eq 0) {
@@ -329,7 +342,7 @@ function New-ExchangeAuthCertificate {
             #>
 
             Write-Verbose "Calling: $($MyInvocation.MyCommand)"
-            $newAuthCertificateActiveOn = (Get-Date)
+            $newAuthCertificateActiveOn = $null
             $renewalSuccessful = $false
             $newAuthCertificateObject = GenerateNewAuthCertificate
 
@@ -339,8 +352,15 @@ function New-ExchangeAuthCertificate {
                 Write-Verbose ("New Auth Certificate with thumbprint: $($newAuthCertificateThumbprint) generated - the existing one will be replaced immediately with the new one")
                 try {
                     Write-Verbose ("[Required] Step 1: Set certificate: $($newAuthCertificateThumbprint) as new Auth Certificate")
-                    if ($PSCmdlet.ShouldProcess("Certificate: $newAuthCertificateThumbprint Date: $newAuthCertificateActiveOn", "Set-AuthConfig")) {
-                        Set-AuthConfig -NewCertificateThumbprint $newAuthCertificateThumbprint -NewCertificateEffectiveDate $newAuthCertificateActiveOn -Force -ErrorAction Stop
+                    if ($PSCmdlet.ShouldProcess("Certificate: $newAuthCertificateThumbprint Date: immediately", "Set-AuthConfig")) {
+                        # We must use Get-Date here to ensure that the date which is passed to NewCertificateEffectiveDate parameter is a valid one
+                        $setAuthConfigParams = @{
+                            NewCertificateThumbprint    = $newAuthCertificateThumbprint
+                            NewCertificateEffectiveDate = ($newAuthCertificateActiveOn = Get-Date)
+                            Force                       = $true
+                            ErrorAction                 = "Stop"
+                        }
+                        Set-AuthConfig @setAuthConfigParams
                     }
 
                     Write-Verbose ("[Required] Step 2: Publish the new Auth Certificate")
diff --git a/Admin/MonitorExchangeAuthCertificate/DataCollection/Get-ExchangeAuthCertificateStatus.ps1 b/Admin/MonitorExchangeAuthCertificate/DataCollection/Get-ExchangeAuthCertificateStatus.ps1
index 2b30b9594f..d6e5e9ffcf 100644
--- a/Admin/MonitorExchangeAuthCertificate/DataCollection/Get-ExchangeAuthCertificateStatus.ps1
+++ b/Admin/MonitorExchangeAuthCertificate/DataCollection/Get-ExchangeAuthCertificateStatus.ps1
@@ -32,8 +32,9 @@ function Get-ExchangeAuthCertificateStatus {
         $configureNextAuthRequired = $false
         $importNextAuthCertificateRequired = $false
 
-        $currentAuthCertificateValidInDays = 0
-        $nextAuthCertificateValidInDays = 0
+        # Make sure to initialize this with -1 as this is needed to properly run the validation in case that we're unable to query this information
+        $currentAuthCertificateValidInDays = -1
+        $nextAuthCertificateValidInDays = -1
 
         $exchangeServersUnreachableList = New-Object 'System.Collections.Generic.List[string]'
         $exchangeServersReachableList = New-Object 'System.Collections.Generic.List[string]'
@@ -116,11 +117,41 @@ function Get-ExchangeAuthCertificateStatus {
                 ($IgnoreUnreachableServers))) {
 
                 if ($exchangeServersReachableList.Count -gt $currentAuthCertificateMissingOnServersList.Count) {
-                    $currentAuthCertificateValidInDays = (($currentAuthCertificate.NotAfter) - (Get-Date)).Days
+                    if ($null -ne $currentAuthCertificate.NotAfter) {
+                        $currentAuthCertificateValidInDays = (($currentAuthCertificate.NotAfter) - (Get-Date)).Days
+
+                        if (($currentAuthCertificate.NotAfter).Date -lt (Get-Date)) {
+                            if ($currentAuthCertificateValidInDays -eq 0) {
+                                Write-Verbose ("The current Auth Certificate has expired today")
+                                $currentAuthCertificateValidInDays = -1
+                            } else {
+                                Write-Verbose ("The current Auth Certificate has already expired {0} days ago" -f [System.Math]::Abs($currentAuthCertificateValidInDays))
+                            }
+                        } else {
+                            Write-Verbose ("The current Auth Certificate is still valid")
+                        }
+                    } else {
+                        Write-Verbose ("There is no Auth Certificate configured")
+                    }
                 }
 
                 if ($exchangeServersReachableList.Count -gt $nextAuthCertificateMissingOnServersList.Count) {
-                    $nextAuthCertificateValidInDays = (($nextAuthCertificate.NotAfter) - (Get-Date)).Days
+                    if ($null -ne $nextAuthCertificate.NotAfter) {
+                        $nextAuthCertificateValidInDays = (($nextAuthCertificate.NotAfter) - (Get-Date)).Days
+
+                        if (($nextAuthCertificate.NotAfter).Date -lt (Get-Date)) {
+                            if ($nextAuthCertificateValidInDays -eq 0) {
+                                Write-Verbose ("The next Auth Certificate has expired today")
+                                $nextAuthCertificateValidInDays = -1
+                            } else {
+                                Write-Verbose ("The next Auth Certificate has already expired {0} days ago" -f [System.Math]::Abs($nextAuthCertificateValidInDays))
+                            }
+                        } else {
+                            Write-Verbose ("The next Auth Certificate is still valid")
+                        }
+                    } else {
+                        Write-Verbose ("There is no next Auth Certificate configured")
+                    }
                 }
 
                 if (($currentAuthCertificateValidInDays -lt 0) -and
diff --git a/Admin/MonitorExchangeAuthCertificate/DataCollection/Tests/Get-ExchangeAuthCertificateStatus.Tests.ps1 b/Admin/MonitorExchangeAuthCertificate/DataCollection/Tests/Get-ExchangeAuthCertificateStatus.Tests.ps1
index 3dda480447..da01f6baca 100644
--- a/Admin/MonitorExchangeAuthCertificate/DataCollection/Tests/Get-ExchangeAuthCertificateStatus.Tests.ps1
+++ b/Admin/MonitorExchangeAuthCertificate/DataCollection/Tests/Get-ExchangeAuthCertificateStatus.Tests.ps1
@@ -254,7 +254,7 @@ Describe "Testing Get-ExchangeAuthCertificateStatus.ps1" {
 
         It "Should Not Return That An Auth Certificate Renewal Action Is Required" {
             $results | Should -Not -BeNullOrEmpty
-            $results.CurrentAuthCertificateLifetimeInDays | Should -Be 0
+            $results.CurrentAuthCertificateLifetimeInDays | Should -Be -1
             $results.ReplaceRequired | Should -Be $false
             $results.ConfigureNextAuthRequired | Should -Be $false
         }
diff --git a/Admin/MonitorExchangeAuthCertificate/MonitorExchangeAuthCertificate.ps1 b/Admin/MonitorExchangeAuthCertificate/MonitorExchangeAuthCertificate.ps1
index b5e74e3136..65795269c4 100644
--- a/Admin/MonitorExchangeAuthCertificate/MonitorExchangeAuthCertificate.ps1
+++ b/Admin/MonitorExchangeAuthCertificate/MonitorExchangeAuthCertificate.ps1
@@ -673,8 +673,10 @@ function Main {
             }
             Write-Host ("")
             Write-Host ("Test result: $($renewalActionWording)") -ForegroundColor Cyan
-            if (($authCertStatus.AuthCertificateMissingOnServers.Count -gt 0) -or
-                ($authCertStatus.NextAuthCertificateMissingOnServers.Count -gt 0)) {
+            if ((($authCertStatus.AuthCertificateMissingOnServers.Count -gt 0) -and
+                ($authCertStatus.CurrentAuthCertificateImportRequired)) -or
+                (($authCertStatus.NextAuthCertificateMissingOnServers.Count -gt 0) -and
+                ($authCertStatus.NextAuthCertificateImportRequired))) {
                 Write-Host ("`rThe script will try to import the certificate to the missing servers automatically (as long as it's valid).") -ForegroundColor Cyan
             }
         }