diff --git a/src/PowerShellEditorServices.Hosting/Commands/StartEditorServicesCommand.cs b/src/PowerShellEditorServices.Hosting/Commands/StartEditorServicesCommand.cs
index 743b6aac99..10de11254d 100644
--- a/src/PowerShellEditorServices.Hosting/Commands/StartEditorServicesCommand.cs
+++ b/src/PowerShellEditorServices.Hosting/Commands/StartEditorServicesCommand.cs
@@ -224,10 +224,7 @@ protected override void EndProcessing()
                 // Create the configuration from parameters
                 EditorServicesConfig editorServicesConfig = CreateConfigObject();
 
-                SessionFileWriter sessionFileWriter = new(_logger, SessionDetailsPath);
-                _logger.Log(PsesLogLevel.Diagnostic, "Session file writer created");
-
-                using EditorServicesLoader psesLoader = EditorServicesLoader.Create(_logger, editorServicesConfig, sessionFileWriter, _loggerUnsubscribers);
+                using EditorServicesLoader psesLoader = EditorServicesLoader.Create(_logger, editorServicesConfig, SessionDetailsPath, _loggerUnsubscribers);
                 _logger.Log(PsesLogLevel.Verbose, "Loading EditorServices");
                 // Synchronously start editor services and wait here until it shuts down.
 #pragma warning disable VSTHRD002
@@ -394,7 +391,7 @@ private string GetProfilePathFromProfileObject(PSObject profileObject, ProfileUs
                 $"{HostProfileId}_profile.ps1");
         }
 
-        // We should only use PSReadLine if we specificied that we want a console repl
+        // We should only use PSReadLine if we specified that we want a console repl
         // and we have not explicitly said to use the legacy ReadLine.
         // We also want it if we are either:
         // * On Windows on any version OR
diff --git a/src/PowerShellEditorServices.Hosting/Configuration/SessionFileWriter.cs b/src/PowerShellEditorServices.Hosting/Configuration/SessionFileWriter.cs
index e7765331aa..623ea8cf30 100644
--- a/src/PowerShellEditorServices.Hosting/Configuration/SessionFileWriter.cs
+++ b/src/PowerShellEditorServices.Hosting/Configuration/SessionFileWriter.cs
@@ -42,15 +42,19 @@ public sealed class SessionFileWriter : ISessionFileWriter
 
         private readonly string _sessionFilePath;
 
+        private readonly Version _powerShellVersion;
+
         /// <summary>
         /// Construct a new session file writer for the given session file path.
         /// </summary>
         /// <param name="logger">The logger to log actions with.</param>
         /// <param name="sessionFilePath">The path to write the session file path to.</param>
-        public SessionFileWriter(HostLogger logger, string sessionFilePath)
+        /// <param name="powerShellVersion">The process's PowerShell version object.</param>
+        public SessionFileWriter(HostLogger logger, string sessionFilePath, Version powerShellVersion)
         {
             _logger = logger;
             _sessionFilePath = sessionFilePath;
+            _powerShellVersion = powerShellVersion;
         }
 
         /// <summary>
@@ -84,11 +88,11 @@ public void WriteSessionStarted(ITransportConfig languageServiceTransport, ITran
                 { "status", "started" },
             };
 
-            if (languageServiceTransport != null)
+            if (languageServiceTransport is not null)
             {
                 sessionObject["languageServiceTransport"] = languageServiceTransport.SessionFileTransportName;
 
-                if (languageServiceTransport.SessionFileEntries != null)
+                if (languageServiceTransport.SessionFileEntries is not null)
                 {
                     foreach (KeyValuePair<string, object> sessionEntry in languageServiceTransport.SessionFileEntries)
                     {
@@ -97,7 +101,7 @@ public void WriteSessionStarted(ITransportConfig languageServiceTransport, ITran
                 }
             }
 
-            if (debugAdapterTransport != null)
+            if (debugAdapterTransport is not null)
             {
                 sessionObject["debugServiceTransport"] = debugAdapterTransport.SessionFileTransportName;
 
@@ -119,6 +123,8 @@ public void WriteSessionStarted(ITransportConfig languageServiceTransport, ITran
         /// <param name="sessionObject">The dictionary representing the session file.</param>
         private void WriteSessionObject(Dictionary<string, object> sessionObject)
         {
+            sessionObject["powerShellVersion"] = _powerShellVersion;
+
             string psModulePath = Environment.GetEnvironmentVariable("PSModulePath");
             string content = null;
             using (SMA.PowerShell pwsh = SMA.PowerShell.Create(RunspaceMode.NewRunspace))
diff --git a/src/PowerShellEditorServices.Hosting/EditorServicesLoader.cs b/src/PowerShellEditorServices.Hosting/EditorServicesLoader.cs
index b9d4097cc9..d5772bb590 100644
--- a/src/PowerShellEditorServices.Hosting/EditorServicesLoader.cs
+++ b/src/PowerShellEditorServices.Hosting/EditorServicesLoader.cs
@@ -49,37 +49,28 @@ public sealed class EditorServicesLoader : IDisposable
         /// </summary>
         /// <param name="logger">The host logger to use.</param>
         /// <param name="hostConfig">The host configuration to start editor services with.</param>
-        /// <param name="sessionFileWriter">The session file writer to write the session file with.</param>
-        /// <returns></returns>
-        public static EditorServicesLoader Create(
-            HostLogger logger,
-            EditorServicesConfig hostConfig,
-            ISessionFileWriter sessionFileWriter) => Create(logger, hostConfig, sessionFileWriter, loggersToUnsubscribe: null);
-
-        /// <summary>
-        /// Create a new Editor Services loader.
-        /// </summary>
-        /// <param name="logger">The host logger to use.</param>
-        /// <param name="hostConfig">The host configuration to start editor services with.</param>
-        /// <param name="sessionFileWriter">The session file writer to write the session file with.</param>
+        /// <param name="sessionDetailsPath">Path to the session file to create on startup or startup failure.</param>
         /// <param name="loggersToUnsubscribe">The loggers to unsubscribe form writing to the terminal.</param>
-        /// <returns></returns>
         public static EditorServicesLoader Create(
             HostLogger logger,
             EditorServicesConfig hostConfig,
-            ISessionFileWriter sessionFileWriter,
+            string sessionDetailsPath,
             IReadOnlyCollection<IDisposable> loggersToUnsubscribe)
         {
-            if (logger == null)
+            if (logger is null)
             {
                 throw new ArgumentNullException(nameof(logger));
             }
 
-            if (hostConfig == null)
+            if (hostConfig is null)
             {
                 throw new ArgumentNullException(nameof(hostConfig));
             }
 
+            Version powerShellVersion = GetPSVersion();
+            SessionFileWriter sessionFileWriter = new(logger, sessionDetailsPath, powerShellVersion);
+            logger.Log(PsesLogLevel.Diagnostic, "Session file writer created");
+
 #if CoreCLR
             // In .NET Core, we add an event here to redirect dependency loading to the new AssemblyLoadContext we load PSES' dependencies into
             logger.Log(PsesLogLevel.Verbose, "Adding AssemblyResolve event handler for new AssemblyLoadContext dependency loading");
@@ -167,7 +158,7 @@ public static EditorServicesLoader Create(
             };
 #endif
 
-            return new EditorServicesLoader(logger, hostConfig, sessionFileWriter, loggersToUnsubscribe);
+            return new EditorServicesLoader(logger, hostConfig, sessionFileWriter, loggersToUnsubscribe, powerShellVersion);
         }
 
         private readonly EditorServicesConfig _hostConfig;
@@ -178,33 +169,38 @@ public static EditorServicesLoader Create(
 
         private readonly IReadOnlyCollection<IDisposable> _loggersToUnsubscribe;
 
+        private readonly Version _powerShellVersion;
+
         private EditorServicesRunner _editorServicesRunner;
 
         private EditorServicesLoader(
             HostLogger logger,
             EditorServicesConfig hostConfig,
             ISessionFileWriter sessionFileWriter,
-            IReadOnlyCollection<IDisposable> loggersToUnsubscribe)
+            IReadOnlyCollection<IDisposable> loggersToUnsubscribe,
+            Version powerShellVersion)
         {
             _logger = logger;
             _hostConfig = hostConfig;
             _sessionFileWriter = sessionFileWriter;
             _loggersToUnsubscribe = loggersToUnsubscribe;
+            _powerShellVersion = powerShellVersion;
         }
 
         /// <summary>
         /// Load Editor Services and its dependencies in an isolated way and start it.
         /// This method's returned task will end when Editor Services shuts down.
         /// </summary>
-        /// <returns></returns>
         public Task LoadAndRunEditorServicesAsync()
         {
             // Log important host information here
             LogHostInformation();
 
+            CheckPowerShellVersion();
+
 #if !CoreCLR
             // Make sure the .NET Framework version supports .NET Standard 2.0
-            CheckNetFxVersion();
+            CheckDotNetVersion();
 #endif
 
             // Add the bundled modules to the PSModulePath
@@ -241,10 +237,30 @@ private static void LoadEditorServices() =>
             // The call within this method is therefore a total no-op
             EditorServicesLoading.LoadEditorServicesForHost();
 
+        private void CheckPowerShellVersion()
+        {
+            PSLanguageMode languageMode = Runspace.DefaultRunspace.SessionStateProxy.LanguageMode;
+
+            _logger.Log(PsesLogLevel.Verbose, $@"
+== PowerShell Details ==
+- PowerShell version: {_powerShellVersion}
+- Language mode:      {languageMode}
+");
+
+            if ((_powerShellVersion < new Version(5, 1))
+                || (_powerShellVersion >= new Version(6, 0) && _powerShellVersion < new Version(7, 2)))
+            {
+                _logger.Log(PsesLogLevel.Error, $"PowerShell {_powerShellVersion} is not supported, please update!");
+                _sessionFileWriter.WriteSessionFailure("powerShellVersion");
+            }
+
+            // TODO: Check if language mode still matters for support.
+        }
+
 #if !CoreCLR
-        private void CheckNetFxVersion()
+        private void CheckDotNetVersion()
         {
-            _logger.Log(PsesLogLevel.Diagnostic, "Checking that .NET Framework version is at least 4.8");
+            _logger.Log(PsesLogLevel.Verbose, "Checking that .NET Framework version is at least 4.8");
             using RegistryKey key = Registry.LocalMachine.OpenSubKey(@"SOFTWARE\Microsoft\Net Framework Setup\NDP\v4\Full");
             object netFxValue = key?.GetValue("Release");
             if (netFxValue == null || netFxValue is not int netFxVersion)
@@ -256,7 +272,8 @@ private void CheckNetFxVersion()
 
             if (netFxVersion < Net48Version)
             {
-                _logger.Log(PsesLogLevel.Warning, $".NET Framework version {netFxVersion} lower than .NET 4.8. This runtime is not supported and you may experience errors. Please update your .NET runtime version.");
+                _logger.Log(PsesLogLevel.Error, $".NET Framework {netFxVersion} is out-of-date, please install at least 4.8: https://dotnet.microsoft.com/en-us/download/dotnet-framework");
+                _sessionFileWriter.WriteSessionFailure("dotNetVersion");
             }
         }
 #endif
@@ -322,30 +339,6 @@ private void LogHostInformation()
  - PowerShell output encoding: {GetPSOutputEncoding()}
 ");
 
-            LogPowerShellDetails();
-
-            LogOperatingSystemDetails();
-        }
-
-        private static string GetPSOutputEncoding()
-        {
-            using SMA.PowerShell pwsh = SMA.PowerShell.Create();
-            return pwsh.AddScript("$OutputEncoding.EncodingName", useLocalScope: true).Invoke<string>()[0];
-        }
-
-        private void LogPowerShellDetails()
-        {
-            PSLanguageMode languageMode = Runspace.DefaultRunspace.SessionStateProxy.LanguageMode;
-
-            _logger.Log(PsesLogLevel.Verbose, $@"
-== PowerShell Details ==
-- PowerShell version: {GetPSVersion()}
-- Language mode:      {languageMode}
-");
-        }
-
-        private void LogOperatingSystemDetails()
-        {
             _logger.Log(PsesLogLevel.Verbose, $@"
 == Environment Details ==
  - OS description:  {RuntimeInformation.OSDescription}
@@ -354,6 +347,12 @@ private void LogOperatingSystemDetails()
 ");
         }
 
+        private static string GetPSOutputEncoding()
+        {
+            using SMA.PowerShell pwsh = SMA.PowerShell.Create();
+            return pwsh.AddScript("$OutputEncoding.EncodingName", useLocalScope: true).Invoke<string>()[0];
+        }
+
         // TODO: Deduplicate this with VersionUtils.
         private static string GetOSArchitecture()
         {
@@ -401,7 +400,7 @@ private void ValidateConfiguration()
             }
         }
 
-        private static object GetPSVersion()
+        private static Version GetPSVersion()
         {
             // In order to read the $PSVersionTable variable,
             // we are forced to create a new runspace to avoid concurrency issues,
@@ -412,7 +411,7 @@ private static object GetPSVersion()
             return typeof(PSObject).Assembly
                 .GetType("System.Management.Automation.PSVersionInfo")
                 .GetMethod("get_PSVersion", BindingFlags.Static | BindingFlags.Public | BindingFlags.NonPublic)
-                .Invoke(null, new object[0] /* Cannot use Array.Empty, since it must work in net452 */);
+                .Invoke(null, new object[0] /* Cannot use Array.Empty, since it must work in net452 */) as Version;
 #pragma warning restore CA1825
         }
     }