diff --git a/src/workerd/server/container-client.c++ b/src/workerd/server/container-client.c++
index 69f2f0c6201..b708eccb323 100644
--- a/src/workerd/server/container-client.c++
+++ b/src/workerd/server/container-client.c++
@@ -1612,6 +1612,15 @@ kj::Promise<kj::Maybe<ContainerClient::SidecarInspectResponse>> ContainerClient:
   };
 }
 
+kj::Promise<void> ContainerClient::ensureSidecarBridgeBypass(kj::String networkCidr) {
+  auto script = kj::str("cidr=$1\n"
+      "iptables -t mangle -C PREROUTING -s \"$cidr\" -d \"$cidr\" -j RETURN 2>/dev/null || "
+      "iptables -t mangle -I PREROUTING 1 -s \"$cidr\" -d \"$cidr\" -j RETURN\n");
+  auto cmd =
+      kj::arr(kj::str("sh"), kj::str("-c"), kj::mv(script), kj::str("sh"), kj::mv(networkCidr));
+  co_await runSimpleExecInContainer(sidecarContainerName, cmd.asPtr());
+}
+
 kj::Promise<void> ContainerClient::updateSidecarEgressPort(
     uint16_t ingressHostPort, uint16_t egressPort) {
   capnp::JsonCodec codec;
@@ -1844,7 +1853,8 @@ kj::Promise<ContainerClient::ExecInspectResponse> ContainerClient::inspectExec(
   };
 }
 
-kj::Promise<void> ContainerClient::runSimpleExec(kj::ArrayPtr<const kj::String> cmd) {
+kj::Promise<void> ContainerClient::runSimpleExecInContainer(
+    kj::StringPtr targetContainerName, kj::ArrayPtr<const kj::String> cmd) {
   capnp::JsonCodec codec;
   codec.handleByAnnotation<docker_api::Docker::ExecCreateRequest>();
 
@@ -1862,7 +1872,7 @@ kj::Promise<void> ContainerClient::runSimpleExec(kj::ArrayPtr<const kj::String>
 
   auto createResponse =
       co_await dockerApiRequest(network, kj::str(dockerPath), kj::HttpMethod::POST,
-          kj::str("/containers/", containerName, "/exec"), codec.encode(createRequest));
+          kj::str("/containers/", targetContainerName, "/exec"), codec.encode(createRequest));
   JSG_REQUIRE(createResponse.statusCode == 201, Error, "Creating helper Docker exec failed with [",
       createResponse.statusCode, "] ", createResponse.body);
 
@@ -1894,6 +1904,10 @@ kj::Promise<void> ContainerClient::runSimpleExec(kj::ArrayPtr<const kj::String>
   }
 }
 
+kj::Promise<void> ContainerClient::runSimpleExec(kj::ArrayPtr<const kj::String> cmd) {
+  co_await runSimpleExecInContainer(containerName, cmd);
+}
+
 kj::Promise<void> ContainerClient::startContainer() {
   auto endpoint = kj::str("/containers/", containerName, "/start");
   // We have to send an empty body since docker API will throw an error if we don't.
@@ -2202,6 +2216,8 @@ kj::Promise<void> ContainerClient::status(StatusContext context) {
     containerSidecarStarted.store(true, std::memory_order_release);
     this->sidecarIngressHostPort = sidecar.ingressHostPort;
     co_await ensureEgressListenerStarted();
+    auto ipamConfig = co_await getDockerBridgeIPAMConfig();
+    co_await ensureSidecarBridgeBypass(kj::mv(ipamConfig.subnet));
     co_await updateSidecarEgressPort(sidecar.ingressHostPort, egressListenerPort);
     co_await readCACert();
   }
@@ -2673,8 +2689,10 @@ kj::Promise<void> ContainerClient::ensureSidecarStarted() {
   KJ_ON_SCOPE_FAILURE(containerSidecarStarted.store(false, std::memory_order_release));
 
   auto ipamConfig = co_await getDockerBridgeIPAMConfig();
+  auto networkCidr = kj::str(ipamConfig.subnet);
   co_await createSidecarContainer(egressListenerPort, kj::mv(ipamConfig.subnet));
   co_await startSidecarContainer();
+  co_await ensureSidecarBridgeBypass(kj::mv(networkCidr));
 
   auto sidecar = KJ_REQUIRE_NONNULL(co_await inspectSidecar(), "started sidecar not running");
   this->sidecarIngressHostPort = sidecar.ingressHostPort;
diff --git a/src/workerd/server/container-client.h b/src/workerd/server/container-client.h
index 1cc6c244bd2..d629fe0c5af 100644
--- a/src/workerd/server/container-client.h
+++ b/src/workerd/server/container-client.h
@@ -163,6 +163,7 @@ class ContainerClient final: public rpc::Container::Server, public kj::Refcounte
 
   kj::Promise<kj::Maybe<InspectResponse>> inspectContainer();
 
+  kj::Promise<void> ensureSidecarBridgeBypass(kj::String networkCidr);
   kj::Promise<void> updateSidecarEgressPort(uint16_t ingressHostPort, uint16_t egressPort);
   kj::Promise<void> updateSidecarEgressConfig(uint16_t ingressHostPort, uint16_t egressPort);
   kj::Promise<void> createContainer(kj::StringPtr effectiveImage,
@@ -176,6 +177,8 @@ class ContainerClient final: public rpc::Container::Server, public kj::Refcounte
       bool attachStderr);
   kj::Promise<kj::Own<kj::AsyncIoStream>> startExec(kj::String execId);
   kj::Promise<ExecInspectResponse> inspectExec(kj::StringPtr execId);
+  kj::Promise<void> runSimpleExecInContainer(kj::StringPtr targetContainerName,
+      kj::ArrayPtr<const kj::String> cmd);
   kj::Promise<void> runSimpleExec(kj::ArrayPtr<const kj::String> cmd);
   kj::Promise<void> startContainer();
   kj::Promise<void> stopContainer();