diff --git a/src/System.Management.Automation/engine/runtime/Binding/Binders.cs b/src/System.Management.Automation/engine/runtime/Binding/Binders.cs
index f84ce6e55a..1bcd9d79d9 100644
--- a/src/System.Management.Automation/engine/runtime/Binding/Binders.cs
+++ b/src/System.Management.Automation/engine/runtime/Binding/Binders.cs
@@ -400,35 +400,34 @@ namespace System.Management.Automation.Language
 
         internal static BindingRestrictions GetLanguageModeCheckIfHasEverUsedConstrainedLanguage()
         {
-            BindingRestrictions languageModeRestriction = BindingRestrictions.Empty;
-
             // Also add a language mode check to detect toggling between language modes
             if (ExecutionContext.HasEverUsedConstrainedLanguage)
             {
                 var context = LocalPipeline.GetExecutionContextFromTLS();
 
-                switch (context.LanguageMode)
-                {
-                    case PSLanguageMode.ConstrainedLanguage:
-                        languageModeRestriction = BindingRestrictions.GetExpressionRestriction(
-                             Expression.Equal(
-                                 Expression.Property(
-                                     ExpressionCache.GetExecutionContextFromTLS,
-                                     CachedReflectionInfo.ExecutionContext_LanguageMode),
-                                 Expression.Constant(PSLanguageMode.ConstrainedLanguage)));
-                        break;
-                    default:
-                        languageModeRestriction = BindingRestrictions.GetExpressionRestriction(
-                             Expression.NotEqual(
-                                 Expression.Property(
-                                     ExpressionCache.GetExecutionContextFromTLS,
-                                     CachedReflectionInfo.ExecutionContext_LanguageMode),
-                                 Expression.Constant(PSLanguageMode.ConstrainedLanguage)));
-                        break;
-                }
+                var tmp = Expression.Variable(typeof(ExecutionContext));
+                var langModeFromContext = Expression.Property(tmp, CachedReflectionInfo.ExecutionContext_LanguageMode);
+                var constrainedLanguageMode = Expression.Constant(PSLanguageMode.ConstrainedLanguage);
+
+                // Execution context might be null if we're called from a thread with no runspace (e.g. a PSObject
+                // is used in some C# w/ dynamic). This is sometimes fine, we don't always need a runspace to access
+                // properties.
+                Expression test = context?.LanguageMode == PSLanguageMode.ConstrainedLanguage
+                    ? Expression.AndAlso(
+                          Expression.NotEqual(tmp, ExpressionCache.NullExecutionContext),
+                          Expression.Equal(langModeFromContext, constrainedLanguageMode))
+                    : Expression.OrElse(
+                          Expression.Equal(tmp, ExpressionCache.NullExecutionContext),
+                          Expression.NotEqual(langModeFromContext, constrainedLanguageMode));
+
+                return BindingRestrictions.GetExpressionRestriction(
+                    Expression.Block(
+                        new[] {tmp},
+                        Expression.Assign(tmp, ExpressionCache.GetExecutionContextFromTLS),
+                        test));
             }
 
-            return languageModeRestriction;
+            return BindingRestrictions.Empty;
         }
 
         internal static BindingRestrictions GetOptionalVersionAndLanguageCheckForType(DynamicMetaObjectBinder binder, Type targetType, int expectedVersionNumber)
@@ -5313,10 +5312,10 @@ namespace System.Management.Automation.Language
                                         new object[] { Name });
         }
 
-        internal static DynamicMetaObject EnsureAllowedInLanguageMode(PSLanguageMode languageMode, DynamicMetaObject target, Object targetValue,
+        internal static DynamicMetaObject EnsureAllowedInLanguageMode(ExecutionContext context, DynamicMetaObject target, Object targetValue,
             string name, bool isStatic, DynamicMetaObject[] args, BindingRestrictions moreTests, string errorID, string resourceString)
         {
-            if (languageMode == PSLanguageMode.ConstrainedLanguage)
+            if (context != null && context.LanguageMode == PSLanguageMode.ConstrainedLanguage)
             {
                 if (!IsAllowedInConstrainedLanguage(targetValue, name, isStatic))
                 {
@@ -5970,7 +5969,7 @@ namespace System.Management.Automation.Language
                 // Validate that this is allowed in the current language mode
                 var context = LocalPipeline.GetExecutionContextFromTLS();
                 DynamicMetaObject runtimeError = PSGetMemberBinder.EnsureAllowedInLanguageMode(
-                    context.LanguageMode, target, targetValue, Name, _static, new[] { value }, restrictions,
+                    context, target, targetValue, Name, _static, new[] { value }, restrictions,
                     "PropertySetterNotSupportedInConstrainedLanguage", ParserStrings.PropertySetConstrainedLanguage);
                 if (runtimeError != null)
                 {
@@ -6460,7 +6459,7 @@ namespace System.Management.Automation.Language
                 // Validate that this is allowed in the current language mode
                 var context = LocalPipeline.GetExecutionContextFromTLS();
                 DynamicMetaObject runtimeError = PSGetMemberBinder.EnsureAllowedInLanguageMode(
-                    context.LanguageMode, target, targetValue, Name, _static, args, restrictions,
+                    context, target, targetValue, Name, _static, args, restrictions,
                     "MethodInvocationNotSupportedInConstrainedLanguage", ParserStrings.InvokeMethodConstrainedLanguage);
                 if (runtimeError != null)
                 {
diff --git a/test/powershell/Language/Scripting/ConstrainedLanguageMode.Tests.ps1 b/test/powershell/Language/Scripting/ConstrainedLanguageMode.Tests.ps1
new file mode 100644
index 0000000000..33ea8b1186
--- /dev/null
+++ b/test/powershell/Language/Scripting/ConstrainedLanguageMode.Tests.ps1
@@ -0,0 +1,42 @@
+
+Describe "Test constrained language mode" -Tags "CI" {
+    It "dynamic invocation on non-PowerShell thread should work" {
+        $refAssemblies = if ($IsCoreCLR) {
+            "Microsoft.CSharp","System.Dynamic.Runtime","System.Management.Automation"
+        }
+        else {
+            "Microsoft.CSharp" 
+        }
+
+        $t,$null = Add-Type -ReferencedAssemblies $refAssemblies -WarningAction Ignore -PassThru @"
+        public class BinderBug$(Get-Date -Format FileDateTime)
+        {
+            public static object Test(System.Management.Automation.PSObject psobj)
+            {
+                // Invoke a method through PSObject, but with dynamic, so we get PowerShell's dynamic site binder involved
+                // And we do this on a different thread so there is no ExecutionContext/runspace to check the language mode
+                // The actual method called doesn't really matter.
+
+                return System.Threading.Tasks.Task.Run(() => ((dynamic)psobj).AddCommand("Get-Command")).Result;
+            }
+        }
+"@
+
+        $o = [powershell]::Create()
+        $t::Test($o) | Should Be $o
+
+        try
+        {
+            # Set language mode to ConstrainedLanguage on a different runspace (so it doesn't affect this runspace)
+            $ps = [powershell]::Create()
+            $null = $ps.AddScript('$ExecutionContext.SessionState.LanguageMode = "ConstrainedLanguage"')
+            $null = $ps.Invoke()
+
+            $t::Test($o) | Should Be $o
+        }
+        finally
+        {
+            $ps.Dispose()
+        }
+    }
+}
\ No newline at end of file