diff --git a/src/core/auto-approval/__tests__/checkAutoApproval.spec.ts b/src/core/auto-approval/__tests__/checkAutoApproval.spec.ts
new file mode 100644
index 00000000000..736899178e7
--- /dev/null
+++ b/src/core/auto-approval/__tests__/checkAutoApproval.spec.ts
@@ -0,0 +1,126 @@
+import { checkAutoApproval } from "../index"
+import type { ExtensionState } from "@roo-code/types"
+
+function makeState(overrides: Record<string, unknown> = {}) {
+	return {
+		autoApprovalEnabled: false,
+		alwaysAllowReadOnly: false,
+		alwaysAllowWrite: false,
+		alwaysAllowExecute: false,
+		alwaysAllowMcp: false,
+		alwaysAllowModeSwitch: false,
+		alwaysAllowSubtasks: false,
+		alwaysAllowFollowupQuestions: false,
+		alwaysAllowReadOnlyOutsideWorkspace: false,
+		alwaysAllowWriteOutsideWorkspace: false,
+		alwaysAllowWriteProtected: false,
+		followupAutoApproveTimeoutMs: 0,
+		mcpServers: {},
+		deniedCommands: [] as string[],
+		allowedCommands: [] as string[],
+		...overrides,
+	} as Pick<ExtensionState, any>
+}
+
+describe("checkAutoApproval — denied commands enforcement", () => {
+	const deniedCommands = ["rm", "sudo"]
+
+	it("should deny a command matching the deny list even when autoApprovalEnabled is false", async () => {
+		const result = await checkAutoApproval({
+			state: makeState({ deniedCommands }),
+			ask: "command",
+			text: "rm -rf /tmp/test",
+		})
+
+		expect(result.decision).toBe("deny")
+	})
+
+	it("should deny a command matching the deny list even when alwaysAllowExecute is false", async () => {
+		const result = await checkAutoApproval({
+			state: makeState({ autoApprovalEnabled: true, deniedCommands }),
+			ask: "command",
+			text: "sudo apt install something",
+		})
+
+		expect(result.decision).toBe("deny")
+	})
+
+	it("should deny a chained command where denied command appears after &&", async () => {
+		const result = await checkAutoApproval({
+			state: makeState({ deniedCommands }),
+			ask: "command",
+			text: "cat file.txt && rm file.txt",
+		})
+
+		expect(result.decision).toBe("deny")
+	})
+
+	it("should deny the exact heredoc bypass scenario from the issue", async () => {
+		const command = [
+			"cat > verify-hook-install.nu << 'HEREDOC'",
+			"use scripts/development/modules/nu/install_hooks.nu [install-git-hooks]",
+			"let project_root = ($env | get -o FILE_PWD | default (pwd))",
+			"install-git-hooks $project_root",
+			"HEREDOC",
+			"nu verify-hook-install.nu && rm verify-hook-install.nu",
+		].join("\n")
+
+		const result = await checkAutoApproval({
+			state: makeState({
+				autoApprovalEnabled: true,
+				alwaysAllowExecute: true,
+				deniedCommands: ["rm"],
+				allowedCommands: ["cat", "nu"],
+			}),
+			ask: "command",
+			text: command,
+		})
+
+		expect(result.decision).toBe("deny")
+	})
+
+	it("should return 'ask' for a non-denied command when autoApprovalEnabled is false", async () => {
+		const result = await checkAutoApproval({
+			state: makeState({ deniedCommands }),
+			ask: "command",
+			text: "git status",
+		})
+
+		expect(result.decision).toBe("ask")
+	})
+
+	it("should not deny when deny list is empty", async () => {
+		const result = await checkAutoApproval({
+			state: makeState(),
+			ask: "command",
+			text: "rm -rf /tmp/test",
+		})
+
+		expect(result.decision).toBe("ask")
+	})
+
+	it("should respect longest prefix match: allowed 'rm -i' overrides denied 'rm'", async () => {
+		const result = await checkAutoApproval({
+			state: makeState({
+				autoApprovalEnabled: true,
+				alwaysAllowExecute: true,
+				deniedCommands: ["rm"],
+				allowedCommands: ["rm -i"],
+			}),
+			ask: "command",
+			text: "rm -i file.txt",
+		})
+
+		expect(result.decision).toBe("approve")
+	})
+
+	it("should return 'ask' when state is undefined", async () => {
+		const result = await checkAutoApproval({
+			state: undefined,
+			ask: "command",
+			text: "rm file",
+		})
+
+		expect(result.decision).toBe("ask")
+	})
+})
diff --git a/src/core/auto-approval/__tests__/commands.spec.ts b/src/core/auto-approval/__tests__/commands.spec.ts
index 90d2808ba9c..09528b012b8 100644
--- a/src/core/auto-approval/__tests__/commands.spec.ts
+++ b/src/core/auto-approval/__tests__/commands.spec.ts
@@ -82,6 +82,46 @@ describe("containsDangerousSubstitution — true positives still caught", () =>
 	})
 })
 
+describe("getCommandDecision — denied commands in chained/wrapped commands", () => {
+	it("should auto_deny when denied command appears after && in a chain", () => {
+		expect(getCommandDecision("cat file.txt && rm file.txt", [], ["rm"])).toBe("auto_deny")
+	})
+
+	it("should auto_deny when denied command appears after || in a chain", () => {
+		expect(getCommandDecision("test -f file || rm file", [], ["rm"])).toBe("auto_deny")
+	})
+
+	it("should auto_deny when denied command appears after ; in a chain", () => {
+		expect(getCommandDecision("echo done; rm -rf /tmp/test", [], ["rm"])).toBe("auto_deny")
+	})
+
+	it("should auto_deny when denied command appears after pipe", () => {
+		expect(getCommandDecision("ls | rm file", [], ["rm"])).toBe("auto_deny")
+	})
+
+	it("should auto_deny for heredoc-style bypass with rm at end (multi-line)", () => {
+		const command = `cat > script.sh << 'HEREDOC'\necho hello\nHEREDOC\nnu script.sh && rm script.sh`
+		expect(getCommandDecision(command, [], ["rm"])).toBe("auto_deny")
+	})
+
+	it("should auto_deny when denied command is the first in a chain", () => {
+		expect(getCommandDecision("rm file && echo done", [], ["rm"])).toBe("auto_deny")
+	})
+
+	it("should auto_deny for the exact issue scenario", () => {
+		const command = `cat > verify-hook-install.nu << 'HEREDOC'\nuse scripts/development/modules/nu/install_hooks.nu [install-git-hooks]\nlet project_root = ($env | get -o FILE_PWD | default (pwd))\ninstall-git-hooks $project_root\nHEREDOC\nnu verify-hook-install.nu && rm verify-hook-install.nu`
+		expect(getCommandDecision(command, [], ["rm"])).toBe("auto_deny")
+	})
+
+	it("should not deny when denied command is not present", () => {
+		expect(getCommandDecision("git status && echo done", [], ["rm"])).toBe("ask_user")
+	})
+
+	it("should respect longest prefix match: allowed 'rm -i' overrides denied 'rm'", () => {
+		expect(getCommandDecision("rm -i file.txt", ["rm -i"], ["rm"])).toBe("auto_approve")
+	})
+})
+
 describe("getCommandDecision — integration with dangerous substitution checks", () => {
 	const allowedCommands = ["node", "echo"]
 
diff --git a/src/core/auto-approval/index.ts b/src/core/auto-approval/index.ts
index c8293c2a79f..b8ff8cb9f60 100644
--- a/src/core/auto-approval/index.ts
+++ b/src/core/auto-approval/index.ts
@@ -59,6 +59,17 @@ export async function checkAutoApproval({
 		return { decision: "approve" }
 	}
 
+	// Always enforce denied commands regardless of auto-approval settings.
+	// This prevents agents from bypassing the deny list by wrapping denied
+	// commands inside chains (&&, ||, ;) or multi-line scripts.
+	if (ask === "command" && text && state?.deniedCommands?.length) {
+		const decision = getCommandDecision(text, state.allowedCommands || [], state.deniedCommands)
+
+		if (decision === "auto_deny") {
+			return { decision: "deny" }
+		}
+	}
+
 	if (!state || !state.autoApprovalEnabled) {
 		return { decision: "ask" }
 	}