diff --git a/packages/testcontainers/src/reaper/reaper.test.ts b/packages/testcontainers/src/reaper/reaper.test.ts
index c90af337c..e022c7e76 100644
--- a/packages/testcontainers/src/reaper/reaper.test.ts
+++ b/packages/testcontainers/src/reaper/reaper.test.ts
@@ -53,6 +53,24 @@ describe.sequential("Reaper", { timeout: 120_000 }, () => {
     expect(reaper2.containerId).toBe(reaper.containerId);
   });
 
+  it("should create new reaper container when existing reaper cannot be reached", async () => {
+    const reaper = await getReaper();
+    vi.resetModules();
+    const unreachablePort = await new RandomPortGenerator().generatePort();
+    const reaperContainerInfo = (await client.container.list()).filter((c) => c.Id === reaper.containerId)[0];
+    reaperContainerInfo.Labels["TESTCONTAINERS_RYUK_TEST_LABEL"] = "false";
+    const reaperPort = reaperContainerInfo.Ports.find((port) => port.PrivatePort == 8080);
+    if (!reaperPort) {
+      throw new Error("Expected Reaper to map exposed port 8080");
+    }
+    reaperPort.PublicPort = unreachablePort;
+    vi.spyOn(client.container, "list").mockResolvedValue([reaperContainerInfo]);
+
+    const reaper2 = await getReaper();
+
+    expect(reaper2.containerId).not.toBe(reaper.containerId);
+  });
+
   it("should use custom port when TESTCONTAINERS_RYUK_PORT is set", async () => {
     const customPort = (await new RandomPortGenerator().generatePort()).toString();
     vi.stubEnv("TESTCONTAINERS_RYUK_PORT", customPort);
diff --git a/packages/testcontainers/src/reaper/reaper.ts b/packages/testcontainers/src/reaper/reaper.ts
index e13ba495c..430043bc5 100644
--- a/packages/testcontainers/src/reaper/reaper.ts
+++ b/packages/testcontainers/src/reaper/reaper.ts
@@ -29,30 +29,44 @@ export async function getReaper(client: ContainerRuntimeClient): Promise<Reaper>
   }
 
   reaper = await withFileLock("testcontainers-node.lock", async () => {
-    const reaperContainer = await findReaperContainer(client);
-    sessionId = reaperContainer?.Labels[LABEL_TESTCONTAINERS_SESSION_ID] ?? new RandomUuid().nextUuid();
+    const reaperContainers = await findReaperContainers(client);
 
     if (process.env.TESTCONTAINERS_RYUK_DISABLED === "true") {
+      sessionId = new RandomUuid().nextUuid();
       return new DisabledReaper(sessionId, "");
-    } else if (reaperContainer) {
-      return await useExistingReaper(reaperContainer, sessionId, client.info.containerRuntime.host);
-    } else {
-      return await createNewReaper(sessionId, client.info.containerRuntime.remoteSocketPath);
     }
+
+    for (const reaperContainer of reaperContainers) {
+      const existingSessionId = reaperContainer.Labels[LABEL_TESTCONTAINERS_SESSION_ID] ?? new RandomUuid().nextUuid();
+      try {
+        sessionId = existingSessionId;
+        return await useExistingReaper(reaperContainer, sessionId, client.info.containerRuntime.host);
+      } catch (error) {
+        const message = error instanceof Error ? error.message : String(error);
+        log.warn(`Failed to reuse existing Reaper: ${message}. Trying another Reaper...`, {
+          containerId: reaperContainer.Id,
+        });
+      }
+    }
+
+    sessionId = new RandomUuid().nextUuid();
+    return await createNewReaper(sessionId, client.info.containerRuntime.remoteSocketPath);
   });
 
   reaper.addSession(sessionId);
   return reaper;
 }
 
-async function findReaperContainer(client: ContainerRuntimeClient): Promise<ContainerInfo | undefined> {
+async function findReaperContainers(client: ContainerRuntimeClient): Promise<ContainerInfo[]> {
   const containers = await client.container.list();
-  return containers.find(
-    (container) =>
-      container.State === "running" &&
-      container.Labels[LABEL_TESTCONTAINERS_RYUK] === "true" &&
-      container.Labels["TESTCONTAINERS_RYUK_TEST_LABEL"] !== "true"
-  );
+  return containers
+    .filter(
+      (container) =>
+        container.State === "running" &&
+        container.Labels[LABEL_TESTCONTAINERS_RYUK] === "true" &&
+        container.Labels["TESTCONTAINERS_RYUK_TEST_LABEL"] !== "true"
+    )
+    .sort((a, b) => b.Created - a.Created);
 }
 
 async function useExistingReaper(reaperContainer: ContainerInfo, sessionId: string, host: string): Promise<Reaper> {