diff --git a/README.md b/README.md
index 211d872d..ad0f0791 100644
--- a/README.md
+++ b/README.md
@@ -17,6 +17,12 @@ OrcaCD is a simple GitOps tool for Docker. It allows you to deploy your applicat
 
 You can get started with OrcaCD by following the guide in the [documentation](https://orcacd.dev).
 
+### Restricted deployment directories
+
+The agent checks deployment paths for symlinks before deploying. A container can create a symlink in a writable bind mount and use it as a mount source on a later deployment to access paths outside its application directory. If directory permissions prevent the agent from inspecting a path, the deployment is rejected.
+
+Prefer granting the agent search permission on the affected parent directories. If that is impractical, you can uncomment the `cap_add` block for `DAC_READ_SEARCH` in the agent's Compose configuration and recreate the agent container. This optional Linux capability bypasses file read and directory read/search permissions for **all files accessible to the agent**, not just the deployments directory. It does not bypass write permissions. It is disabled by default; symlink checks remain enabled.
+
 ## Contribute
 
 You're very welcome to contribute to OrcaCD! Please follow the [contribution guide](https://github.com/OrcaCD/orca-cd/blob/main/CONTRIBUTING.md) to get started. If you wish to contribute to the documentation head over to the [repository](https://github.com/OrcaCD/docs).
diff --git a/backend/internal/agent/docker/deployment_paths.go b/backend/internal/agent/docker/deployment_paths.go
index 94bfe2e5..f5c410de 100644
--- a/backend/internal/agent/docker/deployment_paths.go
+++ b/backend/internal/agent/docker/deployment_paths.go
@@ -28,6 +28,9 @@ func deploymentPathViolation(path, deploymentsDir, applicationDir string) string
 	}
 	link, err := firstSymlink(deploymentsDir, path)
 	if err != nil {
+		if errors.Is(err, os.ErrPermission) {
+			return fmt.Sprintf("could not be checked for symlinks: %v; allow the agent to search the parent directories, or opt in to the agent's DAC_READ_SEARCH capability (bypasses read/search permissions for all files accessible to the agent)", err)
+		}
 		return fmt.Sprintf("could not be checked for symlinks: %v", err)
 	}
 	if link != "" {
diff --git a/backend/internal/agent/docker/deployment_paths_test.go b/backend/internal/agent/docker/deployment_paths_test.go
index acb2b29c..5c5b09c0 100644
--- a/backend/internal/agent/docker/deployment_paths_test.go
+++ b/backend/internal/agent/docker/deployment_paths_test.go
@@ -1,6 +1,7 @@
 package docker
 
 import (
+	"errors"
 	"os"
 	"path/filepath"
 	"strings"
@@ -9,6 +10,36 @@ import (
 	composetypes "github.com/compose-spec/compose-go/v2/types"
 )
 
+func TestDeploymentPaths_RejectsInaccessiblePathsWithGuidance(t *testing.T) {
+	rules := setupDeploymentDirs(t)
+	parent := filepath.Join(rules.applicationDir, "data")
+	source := filepath.Join(parent, "private")
+	if err := os.Mkdir(source, 0o750); err != nil {
+		t.Fatal(err)
+	}
+	if err := os.Chmod(parent, 0); err != nil {
+		t.Fatal(err)
+	}
+	t.Cleanup(func() {
+		//nolint:gosec // Restore directory traversal so t.TempDir can clean up.
+		if err := os.Chmod(parent, 0o750); err != nil {
+			t.Error(err)
+		}
+	})
+	if _, err := os.Lstat(source); !errors.Is(err, os.ErrPermission) {
+		if err == nil {
+			t.Skip("process can bypass directory permissions")
+		}
+		t.Fatal(err)
+	}
+
+	err := checkDeployPolicy(bindMountProject(source), rules)
+	requireErrorContains(t, err, "could not be checked for symlinks")
+	requireErrorContains(t, err, "allow the agent to search the parent directories")
+	requireErrorContains(t, err, "opt in to the agent's DAC_READ_SEARCH capability")
+	requireErrorContains(t, err, "bypasses read/search permissions for all files accessible to the agent")
+}
+
 func setupDeploymentDirs(t *testing.T) pathRules {
 	t.Helper()
 	deploymentsDir := t.TempDir()
diff --git a/docker-compose.yml b/docker-compose.yml
index f0f8b953..5c7b11bc 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -22,6 +22,10 @@ services:
       - no-new-privileges:true
     cap_drop:
       - ALL
+    # Optional: inspect deployment paths inside directories restricted by application containers.
+    # This bypasses read/search permissions for all files accessible to the agent.
+    # cap_add:
+    #   - DAC_READ_SEARCH
     use_api_socket: true # Allows container to access Docker API on host
     volumes:
       - ./deployments:/deployments
diff --git a/e2e/docker-compose.e2e.yml b/e2e/docker-compose.e2e.yml
index 1057c116..2788f016 100644
--- a/e2e/docker-compose.e2e.yml
+++ b/e2e/docker-compose.e2e.yml
@@ -29,6 +29,13 @@ services:
     profiles:
       - agent
     container_name: orca-agent-e2e-test
+    security_opt:
+      - no-new-privileges:true
+    cap_drop:
+      - ALL
+    cap_add:
+      # Exercise the optional capability for restricted deployment directories.
+      - DAC_READ_SEARCH
     use_api_socket: true
     volumes:
       - ./data/agent/deployments:/deployments
diff --git a/e2e/tests/agent.test.ts b/e2e/tests/agent.test.ts
index 6c2fcf09..0e477a36 100644
--- a/e2e/tests/agent.test.ts
+++ b/e2e/tests/agent.test.ts
@@ -136,6 +136,9 @@ test.describe("Agent setup", () => {
 		const compose = await setup.locator("pre").innerText();
 		expect(compose).toContain(`HUB_URL: ${APP_URL}`);
 		expect(compose).toMatch(/image: ghcr\.io\/orcacd\/agent:\S+/);
+		expect(compose).toMatch(/cap_drop:\s+- ALL/);
+		expect(compose).not.toMatch(/^\s*cap_add:/m);
+		expect(compose).toMatch(/# cap_add:\s+#\s+- DAC_READ_SEARCH/);
 		authToken = compose.match(/AUTH_TOKEN: (\S+)/)?.[1] ?? "";
 		expect(authToken).not.toBe("");
 		await setup.getByRole("button", { name: "Close" }).click();
diff --git a/e2e/tests/applications.test.ts b/e2e/tests/applications.test.ts
index 3ec3437d..78820ee0 100644
--- a/e2e/tests/applications.test.ts
+++ b/e2e/tests/applications.test.ts
@@ -15,6 +15,7 @@ import {
 	pullImage,
 	removeApplicationContainers,
 	removeVolumes,
+	runWithAgentVolumes,
 	startContainer,
 	stopContainer,
 } from "./helpers/docker.ts";
@@ -130,7 +131,7 @@ const SAFE_VOLUME = `${SAFE_PROJECT}_data`;
 const safeCompose = policyComposeFile(
 	`    volumes:
       - data:/named
-      - ./bound:/bound
+      - ./bound/data:/bound
 `,
 	`volumes:
   data:
@@ -944,7 +945,7 @@ test.describe("Compose security policy", () => {
 		const bind = mounts.find((mount) => mount.Destination === "/bound");
 		expect(bind?.Type).toBe("bind");
 		// The agent translates the path inside its container to the one on the Docker host
-		expect(bind?.Source).toMatch(new RegExp(`/${SAFE_PROJECT}/bound$`));
+		expect(bind?.Source).toMatch(new RegExp(`/${SAFE_PROJECT}/bound/data$`));
 
 		await expect
 			.poll(() => execInContainer(container.id, ["cat", "/named/file"]), { timeout: 15_000 })
@@ -955,6 +956,35 @@ test.describe("Compose security policy", () => {
 		expect(events).toHaveLength(1);
 		expect(events[0]).toMatchObject({ type: "deployment", status: "succeeded" });
 	});
+
+	test("redeploys through a directory restricted to an application user", async ({ page }) => {
+		const id = policyAppIds.get(SAFE_NAME)!;
+		const parent = `/deployments/${SAFE_PROJECT}/bound`;
+		const restrict = runWithAgentVolumes([
+			"sh",
+			"-ec",
+			`chown 1234:1234 ${parent}; chmod 700 ${parent}`,
+		]);
+		expect(restrict.status, restrict.stderr).toBe(0);
+		try {
+			const before = (await applicationEvents(page, id)).length;
+			expect((await api(page, "POST", `/applications/${id}/deploy`)).status).toBe(202);
+			await expect
+				.poll(async () => (await applicationEvents(page, id)).length, { timeout: 60_000 })
+				.toBe(before + 1);
+			await expect
+				.poll(async () => (await applicationEvents(page, id))[0].status, { timeout: 60_000 })
+				.toBe("succeeded");
+			expect((await getApplication(page, id)).lastSyncError).toBeUndefined();
+		} finally {
+			const restore = runWithAgentVolumes([
+				"sh",
+				"-ec",
+				`chmod 755 ${parent}; chown 0:0 ${parent}`,
+			]);
+			expect(restore.status, restore.stderr).toBe(0);
+		}
+	});
 });
 
 test.describe("Deployment notifications", () => {
diff --git a/e2e/tests/helpers/docker.ts b/e2e/tests/helpers/docker.ts
index 45bed630..41125abc 100644
--- a/e2e/tests/helpers/docker.ts
+++ b/e2e/tests/helpers/docker.ts
@@ -125,7 +125,7 @@ export function inspectContainer(id: string) {
 
 // The deployments directory is owned by root on Linux hosts and the agent image has no shell,
 // so a throwaway container with the agent's volumes reads it
-function runWithAgentVolumes(command: string[]) {
+export function runWithAgentVolumes(command: string[]) {
 	return spawnSync(
 		"docker",
 		["run", "--rm", "--volumes-from", AGENT_CONTAINER, BUSYBOX_IMAGE, ...command],
diff --git a/frontend/src/components/dialogs/agent-setup-dialog.tsx b/frontend/src/components/dialogs/agent-setup-dialog.tsx
index ebdcf65d..1d85bbe9 100644
--- a/frontend/src/components/dialogs/agent-setup-dialog.tsx
+++ b/frontend/src/components/dialogs/agent-setup-dialog.tsx
@@ -49,6 +49,10 @@ export function buildAgentComposeFile({
       - no-new-privileges:true
     cap_drop:
       - ALL
+    # Optional: inspect deployment paths inside directories restricted by application containers.
+    # This bypasses read/search permissions for all files accessible to the agent.
+    # cap_add:
+    #   - DAC_READ_SEARCH
     volumes:
       - ./deployments:/deployments
 `;