diff --git a/src/Orbit.Api/Extensions/ServiceCollectionExtensions.cs b/src/Orbit.Api/Extensions/ServiceCollectionExtensions.cs
index aa53e915..0b3f4a0e 100644
--- a/src/Orbit.Api/Extensions/ServiceCollectionExtensions.cs
+++ b/src/Orbit.Api/Extensions/ServiceCollectionExtensions.cs
@@ -11,6 +11,7 @@
 using Orbit.Api.Authorization;
 using Orbit.Api.Idempotency;
 using Orbit.Api.OAuth;
+using Orbit.Api.Observability;
 using Orbit.Application.Behaviors;
 using Orbit.Application.Common;
 using Orbit.Application.Gamification.Services;
@@ -259,28 +260,9 @@ public static WebApplicationBuilder AddOrbitObservability(this WebApplicationBui
             options.SendDefaultPii = false;
             options.AddExceptionFilterForType<FluentValidation.ValidationException>();
             options.AddExceptionFilterForType<OperationCanceledException>();
-            options.SetBeforeSend(ScrubSensitiveData);
+            options.SetBeforeSend(SentryEventScrubber.Scrub);
         });
 
         return builder;
     }
-
-    private static SentryEvent ScrubSensitiveData(SentryEvent sentryEvent, SentryHint hint)
-    {
-        if (sentryEvent.User is { } user)
-        {
-            user.Email = null;
-            user.Username = null;
-            user.IpAddress = null;
-        }
-
-        if (sentryEvent.Request is { } request)
-        {
-            request.Headers?.Clear();
-            request.Cookies = null;
-            request.Data = null;
-        }
-
-        return sentryEvent;
-    }
 }
diff --git a/src/Orbit.Api/Observability/SentryEventScrubber.cs b/src/Orbit.Api/Observability/SentryEventScrubber.cs
new file mode 100644
index 00000000..6616b188
--- /dev/null
+++ b/src/Orbit.Api/Observability/SentryEventScrubber.cs
@@ -0,0 +1,76 @@
+using Sentry;
+using Sentry.Protocol;
+
+namespace Orbit.Api.Observability;
+
+internal static class SentryEventScrubber
+{
+    private const string RedactedMarker = "[Filtered]";
+
+    private static readonly string[] SensitiveKeyFragments =
+    [
+        "password", "passwd", "secret", "token", "apikey", "api_key",
+        "authorization", "auth", "cookie", "session", "credential",
+        "email", "phone", "ssn", "card", "cvv", "otp", "signature",
+        "bearer", "jwt", "refresh",
+    ];
+
+    public static SentryEvent Scrub(SentryEvent sentryEvent, SentryHint hint)
+    {
+        ScrubUser(sentryEvent);
+        ScrubRequest(sentryEvent);
+        ScrubResponse(sentryEvent);
+        ScrubExtra(sentryEvent);
+        return sentryEvent;
+    }
+
+    private static void ScrubUser(SentryEvent sentryEvent)
+    {
+        if (sentryEvent.User is not { } user)
+            return;
+
+        user.Email = null;
+        user.Username = null;
+        user.IpAddress = null;
+        user.Other.Clear();
+    }
+
+    private static void ScrubRequest(SentryEvent sentryEvent)
+    {
+        if (sentryEvent.Request is not { } request)
+            return;
+
+        request.Headers.Clear();
+        request.Cookies = null;
+        request.Data = null;
+        request.QueryString = null;
+    }
+
+    private static void ScrubResponse(SentryEvent sentryEvent)
+    {
+        foreach (var context in sentryEvent.Contexts.Values)
+        {
+            if (context is not Response response)
+                continue;
+
+            response.Data = null;
+            response.Cookies = null;
+            response.Headers.Clear();
+        }
+    }
+
+    private static void ScrubExtra(SentryEvent sentryEvent)
+    {
+        var sensitiveKeys = sentryEvent.Extra
+            .Where(entry => entry.Value is not null && IsSensitiveKey(entry.Key))
+            .Select(entry => entry.Key)
+            .ToList();
+
+        foreach (var key in sensitiveKeys)
+            sentryEvent.SetExtra(key, RedactedMarker);
+    }
+
+    private static bool IsSensitiveKey(string key) =>
+        SensitiveKeyFragments.Any(fragment =>
+            key.Contains(fragment, StringComparison.OrdinalIgnoreCase));
+}
diff --git a/tests/Orbit.Infrastructure.Tests/Observability/SentryEventScrubberTests.cs b/tests/Orbit.Infrastructure.Tests/Observability/SentryEventScrubberTests.cs
new file mode 100644
index 00000000..9a75b4d5
--- /dev/null
+++ b/tests/Orbit.Infrastructure.Tests/Observability/SentryEventScrubberTests.cs
@@ -0,0 +1,105 @@
+using FluentAssertions;
+using Orbit.Api.Observability;
+using Sentry;
+using Sentry.Protocol;
+
+namespace Orbit.Infrastructure.Tests.Observability;
+
+public class SentryEventScrubberTests
+{
+    [Fact]
+    public void Scrub_RemovesResponseBodyHeadersAndCookies_WhenResponseContextPresent()
+    {
+        var sentryEvent = new SentryEvent();
+        var response = sentryEvent.Contexts.Response;
+        response.Data = "{\"token\":\"live-secret\"}";
+        response.Cookies = "session=abc";
+        response.Headers["Set-Cookie"] = "session=abc";
+
+        SentryEventScrubber.Scrub(sentryEvent, new SentryHint());
+
+        var scrubbed = sentryEvent.Contexts.Response;
+        scrubbed.Data.Should().BeNull();
+        scrubbed.Cookies.Should().BeNull();
+        scrubbed.Headers.Should().BeEmpty();
+    }
+
+    [Fact]
+    public void Scrub_DoesNotAddResponseContext_WhenNonePresent()
+    {
+        var sentryEvent = new SentryEvent();
+
+        SentryEventScrubber.Scrub(sentryEvent, new SentryHint());
+
+        sentryEvent.Contexts.ContainsKey(Response.Type).Should().BeFalse();
+    }
+
+    [Fact]
+    public void Scrub_ClearsUserPii_IncludingOtherDictionary()
+    {
+        var sentryEvent = new SentryEvent
+        {
+            User = new SentryUser
+            {
+                Email = "alice@example.com",
+                Username = "alice",
+                IpAddress = "203.0.113.7",
+            },
+        };
+        sentryEvent.User.Other["ssn"] = "123-45-6789";
+
+        SentryEventScrubber.Scrub(sentryEvent, new SentryHint());
+
+        sentryEvent.User.Email.Should().BeNull();
+        sentryEvent.User.Username.Should().BeNull();
+        sentryEvent.User.IpAddress.Should().BeNull();
+        sentryEvent.User.Other.Should().BeEmpty();
+    }
+
+    [Fact]
+    public void Scrub_ClearsRequestBodyCookiesHeadersAndQueryString()
+    {
+        var sentryEvent = new SentryEvent
+        {
+            Request = new SentryRequest
+            {
+                Data = "{\"password\":\"hunter2\"}",
+                Cookies = "session=abc",
+                QueryString = "token=live-secret&email=alice@example.com",
+            },
+        };
+        sentryEvent.Request.Headers["Authorization"] = "Bearer live-secret";
+
+        SentryEventScrubber.Scrub(sentryEvent, new SentryHint());
+
+        sentryEvent.Request.Data.Should().BeNull();
+        sentryEvent.Request.Cookies.Should().BeNull();
+        sentryEvent.Request.QueryString.Should().BeNull();
+        sentryEvent.Request.Headers.Should().BeEmpty();
+    }
+
+    [Fact]
+    public void Scrub_RedactsKnownPiiKeysInExtra_ButKeepsBenignKeys()
+    {
+        var sentryEvent = new SentryEvent();
+        sentryEvent.SetExtra("authToken", "live-secret");
+        sentryEvent.SetExtra("userEmail", "alice@example.com");
+        sentryEvent.SetExtra("habitCount", 7);
+
+        SentryEventScrubber.Scrub(sentryEvent, new SentryHint());
+
+        sentryEvent.Extra["authToken"].Should().Be("[Filtered]");
+        sentryEvent.Extra["userEmail"].Should().Be("[Filtered]");
+        sentryEvent.Extra["habitCount"].Should().Be(7);
+    }
+
+    [Fact]
+    public void Scrub_ReturnsSameEvent_WhenNoSensitiveDataPresent()
+    {
+        var sentryEvent = new SentryEvent();
+
+        var result = SentryEventScrubber.Scrub(sentryEvent, new SentryHint());
+
+        result.Should().BeSameAs(sentryEvent);
+    }
+}