diff --git a/samples/Sentry.Samples.Console.Customized/Program.cs b/samples/Sentry.Samples.Console.Customized/Program.cs
index 7a106f0263..63539e2fd9 100644
--- a/samples/Sentry.Samples.Console.Customized/Program.cs
+++ b/samples/Sentry.Samples.Console.Customized/Program.cs
@@ -1,6 +1,7 @@
 using System;
 using System.Net.Http;
 using System.Reflection;
+using System.Runtime.CompilerServices;
 using System.Threading.Tasks;
 using Sentry;
 using Sentry.Extensibility;
@@ -47,6 +48,9 @@ await SentrySdk.ConfigureScopeAsync(async scope =>
             // Before excluding all prefixed 'LibraryX.', any stack trace from a type namespaced 'LibraryX.Core' will be considered InApp.
             o.AddInAppInclude("LibraryX.Core");
 
+            // Send events whe unoptimized assemblies are detected
+            o.NotifyUnoptimizedAssembly = true;
+
             // Send personal identifiable information like the username logged on to the computer and machine name
             o.SendDefaultPii = true;
 
@@ -108,6 +112,10 @@ await SentrySdk.ConfigureScopeAsync(async scope =>
             SentrySdk.AddBreadcrumb(
                 "A 'bad breadcrumb' that will be rejected because of 'BeforeBreadcrumb callback above.'");
 
+            // Because 'NotifyUnoptimizedAssembly' is enabled, calling this method will raise an event to alert
+            // that an Assembly that is compiled for Debug was loaded.
+            LoadUnoptimizedAssembly();
+
             // Data added to the root scope (no PushScope called up to this point)
             // The modifications done here will affect all events sent and will propagate to child scopes.
             await SentrySdk.ConfigureScopeAsync(async scope =>
@@ -147,7 +155,6 @@ await SentrySdk.ConfigureScopeAsync(async scope =>
                 SentrySdk.CaptureException(error);
             }
 
-
             var count = 10;
             for (var i = 0; i < count; i++)
             {
@@ -196,6 +203,13 @@ await SentrySdk.ConfigureScopeAsync(async scope =>
         }  // On Dispose: SDK closed, events queued are flushed/sent to Sentry
     }
 
+    [MethodImpl(MethodImplOptions.NoInlining)]
+    private static void LoadUnoptimizedAssembly()
+    {
+        // https://twitter.com/jeremydmiller/status/777571510919630848
+        Console.WriteLine(typeof(StructureMap.Container).Assembly.GetName().Version);
+    }
+
     private class AdminPartMiddleware
     {
         private readonly ISentryClient _adminClient;
diff --git a/samples/Sentry.Samples.Console.Customized/Sentry.Samples.Console.Customized.csproj b/samples/Sentry.Samples.Console.Customized/Sentry.Samples.Console.Customized.csproj
index 70771ec60a..9de0801c9a 100644
--- a/samples/Sentry.Samples.Console.Customized/Sentry.Samples.Console.Customized.csproj
+++ b/samples/Sentry.Samples.Console.Customized/Sentry.Samples.Console.Customized.csproj
@@ -5,6 +5,8 @@
     <TargetFrameworks>netcoreapp2.1;net472</TargetFrameworks>
     <!--Set explicitly to demonstrate one way of defining the Sentry Release-->
     <GenerateAssemblyInformationalVersionAttribute>false</GenerateAssemblyInformationalVersionAttribute>
+    <!-- To be able to load structuremap 4.4.0 which is unsigned-->
+    <SignAssembly>false</SignAssembly>
   </PropertyGroup>
 
   <ItemGroup>
@@ -14,5 +16,8 @@
     <Reference Include="System.Net.Http" />
     <Reference Include="Microsoft.CSharp" />
   </ItemGroup>
+  <ItemGroup>
+    <PackageReference Include="structuremap" Version="4.4.0" />
+  </ItemGroup>
 
 </Project>
diff --git a/src/Sentry/Integrations/UnoptimizedAssemblyIntegration.cs b/src/Sentry/Integrations/UnoptimizedAssemblyIntegration.cs
new file mode 100644
index 0000000000..831d34a712
--- /dev/null
+++ b/src/Sentry/Integrations/UnoptimizedAssemblyIntegration.cs
@@ -0,0 +1,68 @@
+using System;
+using System.Linq;
+using Sentry.Extensibility;
+using Sentry.Protocol;
+using Sentry.Reflection;
+
+namespace Sentry.Integrations
+{
+    /// <summary>
+    /// An integration that emits events when detects assemblies compiled for debug.
+    /// </summary>
+    public class UnoptimizedAssemblyIntegration : ISdkIntegration
+    {
+        /// <summary>
+        /// Registers the integration with the hub and options.
+        /// </summary>
+        /// <param name="hub">The hub to use to send events.</param>
+        /// <param name="options">The options to configure the integration.</param>
+        public void Register(IHub hub, SentryOptions options)
+        {
+            if (options.NotifyUnoptimizedAssembly)
+            {
+                options.DiagnosticLogger?.LogDebug("Subscribing to AssemblyLoad to detect unoptimized assemblies.");
+                // TODO: .NET Core equivalent
+                AppDomain.CurrentDomain.AssemblyLoad += (sender, args) =>
+                {
+                    if (!args.LoadedAssembly.IsOptimized())
+                    {
+                        CaptureEvent(hub, options, args.LoadedAssembly.FullName);
+                        hub.FlushAsync(TimeSpan.FromSeconds(10)).GetAwaiter().GetResult();
+                    }
+                };
+
+                var unoptimizedAssemblies = AppDomain.CurrentDomain.GetAssemblies()
+                    .Where(a => !a.IsOptimized())
+                    .Select(a => a.FullName)
+                    .ToArray();
+
+                if (unoptimizedAssemblies.Any())
+                {
+                    CaptureEvent(hub, options, unoptimizedAssemblies);
+                }
+            }
+        }
+
+        private static void CaptureEvent(IHub hub, SentryOptions options, params string[] assemblies)
+        {
+            if (assemblies.Length > 0)
+            {
+                options.DiagnosticLogger?.LogInfo("Unoptimized Assembly found. Raising event for {count} assemblies", assemblies.Length);
+                using (hub.PushScope())
+                {
+                    hub.ConfigureScope(s =>
+                    {
+                        s.SetFingerprint(new[] {"UnoptimizedAssemblyIntegration"});
+                        foreach (var asm in assemblies)
+                        {
+                            options.DiagnosticLogger?.LogInfo("Unoptimized Assembly: {asm}", asm);
+                            s.SetExtra("unoptimized-assembly", asm);
+                        }
+                        s.Level = SentryLevel.Warning;
+                    });
+                    hub.CaptureMessage("Unoptimized assembly detected.");
+                }
+            }
+        }
+    }
+}
diff --git a/src/Sentry/Reflection/AssemblyExtensions.cs b/src/Sentry/Reflection/AssemblyExtensions.cs
index 4a9836d0cb..76648ed708 100644
--- a/src/Sentry/Reflection/AssemblyExtensions.cs
+++ b/src/Sentry/Reflection/AssemblyExtensions.cs
@@ -1,4 +1,5 @@
 using System.ComponentModel;
+using System.Diagnostics;
 using System.Reflection;
 using Sentry.Protocol;
 
@@ -29,5 +30,20 @@ public static SdkVersion GetNameAndVersion(this Assembly asm)
 
             return new SdkVersion { Name = name, Version = version };
         }
+
+        /// <summary>
+        /// Whether the assembly was compiled with the optimize+ flag
+        /// </summary>
+        /// <param name="asm">The assembly to verify the optimization flag</param>
+        /// <returns>
+        /// true if no <see cref="DebuggableAttribute"/> exists or
+        /// <see cref="DebuggableAttribute.IsJITOptimizerDisabled"/> is false,
+        /// otherwise, false.
+        /// </returns>
+        public static bool IsOptimized(this Assembly asm)
+        {
+            var att = asm.GetCustomAttribute<DebuggableAttribute>();
+            return att == null || att.IsJITOptimizerDisabled == false;
+        }
     }
 }
diff --git a/src/Sentry/SentryOptions.cs b/src/Sentry/SentryOptions.cs
index 25c28d1d84..1a721f8e14 100644
--- a/src/Sentry/SentryOptions.cs
+++ b/src/Sentry/SentryOptions.cs
@@ -349,6 +349,11 @@ public IDiagnosticLogger DiagnosticLogger
         /// </summary>
         public bool ReportAssemblies { get; set; } = true;
 
+        /// <summary>
+        /// Whether the SDK should raise events if unoptimized assemblies are loaded.
+        /// </summary>
+        public bool NotifyUnoptimizedAssembly { get; set; }
+
         /// <summary>
         /// What modes to use for event automatic deduplication
         /// </summary>
@@ -411,7 +416,8 @@ public SentryOptions()
             Integrations
                 = ImmutableList.Create<ISdkIntegration>(
                     new AppDomainUnhandledExceptionIntegration(),
-                    new AppDomainProcessExitIntegration());
+                    new AppDomainProcessExitIntegration(),
+                    new UnoptimizedAssemblyIntegration());
 
             InAppExclude
                 = ImmutableList.Create(