diff --git a/Diagnostics/HealthChecker/Analyzer/Invoke-AnalyzerOsInformation.ps1 b/Diagnostics/HealthChecker/Analyzer/Invoke-AnalyzerOsInformation.ps1
index 2b3062f39..dc267fb8f 100644
--- a/Diagnostics/HealthChecker/Analyzer/Invoke-AnalyzerOsInformation.ps1
+++ b/Diagnostics/HealthChecker/Analyzer/Invoke-AnalyzerOsInformation.ps1
@@ -487,10 +487,13 @@ function Invoke-AnalyzerOsInformation {
         $days = 7
         $testDate = (Get-Date).AddDays(-$days)
         foreach ($logType in $osInformation.EventLogInformation.Keys) {
-            if ($osInformation.EventLogInformation[$logType].LastLogEntry -gt $testDate) {
+            $logInfo = $osInformation.EventLogInformation[$logType]
+            # If the log isn't at the max limit, it is possible that they just cleared the logs or on a new server. This should be rare scenario.
+            if ($logInfo.LastLogEntry -gt $testDate -and
+                $logInfo.FileSize -ge $logInfo.MaxSize) {
                 $params = $baseParams + @{
                     Name             = "Event Log - $logType"
-                    Details          = "--ERROR-- Not enough logs to cover $days days. Last log entry is at $($osInformation.EventLogInformation[$logType].LastLogEntry)." +
+                    Details          = "--ERROR-- Not enough logs to cover $days days. Last log entry is at $($logInfo.LastLogEntry)." +
                     " This could cause issues with determining Root Cause Analysis."
                     DisplayWriteType = "Red"
                 }
diff --git a/Diagnostics/HealthChecker/DataCollection/ServerInformation/Get-EventLogInformation.ps1 b/Diagnostics/HealthChecker/DataCollection/ServerInformation/Get-EventLogInformation.ps1
index 8c83abbc7..54b0918f0 100644
--- a/Diagnostics/HealthChecker/DataCollection/ServerInformation/Get-EventLogInformation.ps1
+++ b/Diagnostics/HealthChecker/DataCollection/ServerInformation/Get-EventLogInformation.ps1
@@ -19,6 +19,7 @@ function Get-EventLogInformation {
                 $results.Add($log, ([PSCustomObject]@{
                             LastLogEntry = $lastLogEntry.TimeCreated
                             MaxSize      = $listLog.MaximumSizeInBytes
+                            FileSize     = $listLog.FileSize
                             LogMode      = $listLog.LogMode.ToString()
                             IsEnabled    = $listLog.IsEnabled
                             LogFilePath  = $listLog.LogFilePath
diff --git a/Diagnostics/HealthChecker/Tests/HealthChecker.E19.Scenarios.Tests.ps1 b/Diagnostics/HealthChecker/Tests/HealthChecker.E19.Scenarios.Tests.ps1
index c2c8e3c0c..bad4fafa8 100644
--- a/Diagnostics/HealthChecker/Tests/HealthChecker.E19.Scenarios.Tests.ps1
+++ b/Diagnostics/HealthChecker/Tests/HealthChecker.E19.Scenarios.Tests.ps1
@@ -107,8 +107,6 @@ Describe "Testing Health Checker by Mock Data Imports" {
         It "Event Log Size Test" {
             GetObject "Event Log - Application" |
                 Should -BeLike "--ERROR-- Not enough logs to cover 7 days. Last log entry is at *. This could cause issues with determining Root Cause Analysis."
-            GetObject "Event Log - System" |
-                Should -BeLike "--ERROR-- Not enough logs to cover 7 days. Last log entry is at *. This could cause issues with determining Root Cause Analysis."
         }
 
         It "TCP Keep Alive Time" {