diff --git a/agent_api/src/main/java/dev/aikido/agent_api/SetRateLimitGroup.java b/agent_api/src/main/java/dev/aikido/agent_api/SetRateLimitGroup.java
index 7ef31cac4..c1f65edef 100644
--- a/agent_api/src/main/java/dev/aikido/agent_api/SetRateLimitGroup.java
+++ b/agent_api/src/main/java/dev/aikido/agent_api/SetRateLimitGroup.java
@@ -17,6 +17,9 @@ public static void setRateLimitGroup(String groupId) {
 
         ContextObject currentContext = Context.get();
         if (currentContext == null) {
+            if (Context.isBypassed()) {
+                return;
+            }
             logger.warn("setRateLimitGroup(...) was called without a context. Make sure to call setRateLimitGroup(...) within an HTTP request.");
             return;
         }
diff --git a/agent_api/src/main/java/dev/aikido/agent_api/collectors/WebRequestCollector.java b/agent_api/src/main/java/dev/aikido/agent_api/collectors/WebRequestCollector.java
index 1d66a2126..705635775 100644
--- a/agent_api/src/main/java/dev/aikido/agent_api/collectors/WebRequestCollector.java
+++ b/agent_api/src/main/java/dev/aikido/agent_api/collectors/WebRequestCollector.java
@@ -46,6 +46,7 @@ public static Res report(ContextObject newContext) {
         PendingHostnamesStore.clear();
 
         if (config.isIpBypassed(newContext.getRemoteAddress())) {
+            Context.markBypassed();
             return null; // do not set context when the IP address is bypassed (zen = off)
         }
 
diff --git a/agent_api/src/main/java/dev/aikido/agent_api/context/Context.java b/agent_api/src/main/java/dev/aikido/agent_api/context/Context.java
index 0389cc903..fc2521401 100644
--- a/agent_api/src/main/java/dev/aikido/agent_api/context/Context.java
+++ b/agent_api/src/main/java/dev/aikido/agent_api/context/Context.java
@@ -6,6 +6,8 @@ public final class Context {
     private Context() {}
 
     static final ThreadLocal<ContextObject> threadLocalContext = new ThreadLocal<>();
+    // Bypassed requests have no context, so this flag tells them apart from code running outside a request.
+    static final ThreadLocal<Boolean> threadLocalBypassed = ThreadLocal.withInitial(() -> false);
     public static ContextObject get() {
         return threadLocalContext.get();
     }
@@ -14,5 +16,12 @@ public static void set(ContextObject contextObject) {
     }
     public static void reset() {
         threadLocalContext.remove();
+        threadLocalBypassed.remove();
+    }
+    public static void markBypassed() {
+        threadLocalBypassed.set(true);
+    }
+    public static boolean isBypassed() {
+        return threadLocalBypassed.get();
     }
 }
diff --git a/agent_api/src/test/java/SetRateLimitGroupTest.java b/agent_api/src/test/java/SetRateLimitGroupTest.java
index d82bbd13f..624676770 100644
--- a/agent_api/src/test/java/SetRateLimitGroupTest.java
+++ b/agent_api/src/test/java/SetRateLimitGroupTest.java
@@ -39,7 +39,7 @@ public static void clean() {
 
     @AfterEach
     public void tearDown() throws SQLException {
-        Context.set(null);
+        Context.reset();
     }
 
     @Test
@@ -58,6 +58,16 @@ public void testWithNoContext(StdOut out) throws SQLException, IOException {
         assertTrue(out.capturedString().contains("setRateLimitGroup(...) was called without a context. Make sure to call setRateLimitGroup(...) within an HTTP request."));
     }
 
+    @Test
+    @StdIo
+    public void testWithBypassedRequestDoesNotWarn(StdOut out) {
+        Context.markBypassed();
+
+        SetRateLimitGroup.setRateLimitGroup("id");
+
+        assertFalse(out.capturedString().contains("was called without a context"));
+    }
+
     @Test
     @StdIo
     public void testEmptyGroupId(StdOut out) throws SQLException {
diff --git a/agent_api/src/test/java/collectors/WebRequestCollectorTest.java b/agent_api/src/test/java/collectors/WebRequestCollectorTest.java
index d47e639a9..6ff97791a 100644
--- a/agent_api/src/test/java/collectors/WebRequestCollectorTest.java
+++ b/agent_api/src/test/java/collectors/WebRequestCollectorTest.java
@@ -49,6 +49,23 @@ void testReport_contextSet() {
 
     }
 
+    @Test
+    void testReport_bypassedIpIsMarkedUntilNextRequest() {
+        List<String> bypassedIps = List.of("192.168.1.1");
+        ServiceConfigStore.updateFromAPIResponse(new APIResponse(
+                true, "", getUnixTimeMS(), List.of(), List.of(), bypassedIps, false, null, true, false, List.of(), 0
+        ));
+
+        WebRequestCollector.report(contextObject);
+        assertNull(Context.get());
+        assertTrue(Context.isBypassed());
+
+        contextObject.setIp("10.0.0.1");
+        WebRequestCollector.report(contextObject);
+        assertNotNull(Context.get());
+        assertFalse(Context.isBypassed());
+    }
+
     @Test
     void testReport_ipNotAllowed() {
         setEmptyConfigWithEndpointList(List.of(new Endpoint(