diff --git a/Diagnostics/HealthChecker/Analyzer/Invoke-AnalyzerExchangeInformation.ps1 b/Diagnostics/HealthChecker/Analyzer/Invoke-AnalyzerExchangeInformation.ps1
index a0e81c386..49cc2b6a2 100644
--- a/Diagnostics/HealthChecker/Analyzer/Invoke-AnalyzerExchangeInformation.ps1
+++ b/Diagnostics/HealthChecker/Analyzer/Invoke-AnalyzerExchangeInformation.ps1
@@ -241,7 +241,7 @@ function Invoke-AnalyzerExchangeInformation {
         }
 
         $params = $baseParams + @{
-            Name                   = "Remaining Trail Period"
+            Name                   = "Remaining Trial Period"
             Details                = $details
             DisplayWriteType       = $displayWriteType
             DisplayCustomTabNumber = 2
diff --git a/Diagnostics/HealthChecker/Analyzer/Invoke-AnalyzerKnownBuildIssues.ps1 b/Diagnostics/HealthChecker/Analyzer/Invoke-AnalyzerKnownBuildIssues.ps1
index f970b4846..77bc4d5a8 100644
--- a/Diagnostics/HealthChecker/Analyzer/Invoke-AnalyzerKnownBuildIssues.ps1
+++ b/Diagnostics/HealthChecker/Analyzer/Invoke-AnalyzerKnownBuildIssues.ps1
@@ -260,6 +260,20 @@ function Invoke-AnalyzerKnownBuildIssues {
             InformationUrl          = (GetKnownIssueInformation @infoParams)
         }
         TestForKnownBuildIssues @params
+
+        Write-Verbose "Test for known transport pickup issue for version number."
+        $infoParams = @{
+            Name = "Known Issue when sending email with Pickup Folder is using Admin Display Version vs Installed Version"
+            Url  = "https://support.microsoft.com/topic/email-sent-through-pickup-folder-displays-admin-version-068ae880-5bbf-43f0-a1fa-24a78f31635f"
+        }
+        $params = @{
+            CurrentVersion          = $currentVersion
+            KnownBuildIssuesToFixes = @((GetKnownIssueBuildInformation "15.2.1544.0" "15.2.1544.14"),
+                (GetKnownIssueBuildInformation "15.2.000.000" "15.2.1258.39" -BuildBound $false),
+                (GetKnownIssueBuildInformation "15.1.000.000" "15.1.2507.44" -BuildBound $false))
+            InformationUrl          = (GetKnownIssueInformation @infoParams)
+        }
+        TestForKnownBuildIssues @params
     } catch {
         Write-Verbose "Failed to run TestForKnownBuildIssues"
         Invoke-CatchActions
diff --git a/Diagnostics/HealthChecker/Analyzer/Tests/Invoke-AnalyzerKnownBuildIssues.Tests.ps1 b/Diagnostics/HealthChecker/Analyzer/Tests/Invoke-AnalyzerKnownBuildIssues.Tests.ps1
index fd23d29b0..48444c58d 100644
--- a/Diagnostics/HealthChecker/Analyzer/Tests/Invoke-AnalyzerKnownBuildIssues.Tests.ps1
+++ b/Diagnostics/HealthChecker/Analyzer/Tests/Invoke-AnalyzerKnownBuildIssues.Tests.ps1
@@ -71,5 +71,25 @@ Describe "Testing Known Build Issue Main Logic" {
             } `
                 -KnownIssue (GetKnownIssueBuildInformation -BuildNumber "15.2.2375.17" -FixBuildNumber $null)
         }
+
+        It "Testing Issue always been there" {
+            TestPesterResults -TestGroup @{
+                "15.2.1544.14" = $false
+                "15.2.1544.13" = $false # This is false, but the next test it should be true
+                "15.2.1258.39" = $false
+                "15.2.1258.38" = $true
+                "15.2.1118.40" = $true
+            } `
+                -KnownIssue (GetKnownIssueBuildInformation -BuildNumber "15.2.0.0" -FixBuildNumber "15.2.1258.39" -BuildBound $false)
+
+            TestPesterResults -TestGroup @{
+                "15.2.1544.14" = $false
+                "15.2.1544.13" = $true
+                "15.2.1258.39" = $false
+                "15.2.1258.38" = $false
+                "15.2.1118.40" = $false
+            } `
+                -KnownIssue (GetKnownIssueBuildInformation -BuildNumber "15.2.1544.0" -FixBuildNumber "15.2.1544.14" -BuildBound $true)
+        }
     }
 }
diff --git a/Diagnostics/HealthChecker/Tests/HealthChecker.E16.Main.Tests.ps1 b/Diagnostics/HealthChecker/Tests/HealthChecker.E16.Main.Tests.ps1
index acf72215e..4e4b3b717 100644
--- a/Diagnostics/HealthChecker/Tests/HealthChecker.E16.Main.Tests.ps1
+++ b/Diagnostics/HealthChecker/Tests/HealthChecker.E16.Main.Tests.ps1
@@ -33,7 +33,7 @@ Describe "Testing Health Checker by Mock Data Imports - Exchange 2016" {
             TestObjectMatch "Extended Protection Enabled (Any VDir)" $false
             TestObjectMatch "Setting Overrides Detected" $false
             TestObjectMatch "Exchange Server Membership" "Passed"
-            $Script:ActiveGrouping.Count | Should -Be 19
+            $Script:ActiveGrouping.Count | Should -Be 22
         }
 
         It "Display Results - Organization Information" {
diff --git a/Diagnostics/HealthChecker/Tests/HealthChecker.E19.Main.Tests.ps1 b/Diagnostics/HealthChecker/Tests/HealthChecker.E19.Main.Tests.ps1
index 69b153f9e..53fb9c87e 100644
--- a/Diagnostics/HealthChecker/Tests/HealthChecker.E19.Main.Tests.ps1
+++ b/Diagnostics/HealthChecker/Tests/HealthChecker.E19.Main.Tests.ps1
@@ -26,7 +26,7 @@ Describe "Testing Health Checker by Mock Data Imports" {
             TestObjectMatch "End Of Life" $true -WriteType "Yellow" # This is going to change to red once we get 178 out
             TestObjectMatch "Server Role" "Mailbox"
             TestObjectMatch "Edition" "Warning - StandardEvaluation" -WriteType "Yellow"
-            TestObjectMatch "Remaining Trail Period" "Error - 00:00:00" -WriteType "Red"
+            TestObjectMatch "Remaining Trial Period" "Error - 00:00:00" -WriteType "Red"
             TestObjectMatch "DAG Name" "Standalone Server"
             TestObjectMatch "AD Site" "Default-First-Site-Name"
             TestObjectMatch "MRS Proxy Enabled" "False"
@@ -37,7 +37,7 @@ Describe "Testing Health Checker by Mock Data Imports" {
             TestObjectMatch "Monitoring Overrides Detected" $false
             TestObjectMatch "Out of Date" $true -WriteType "Red"
             TestObjectMatch "Exchange Server Membership" "Passed"
-            $Script:ActiveGrouping.Count | Should -Be 19
+            $Script:ActiveGrouping.Count | Should -Be 22
         }
 
         It "Display Results - Organization Information" {