diff --git a/packages/pi-coding-agent/src/core/tools/bash-interceptor.test.ts b/packages/pi-coding-agent/src/core/tools/bash-interceptor.test.ts
new file mode 100644
index 000000000..315fc4dc0
--- /dev/null
+++ b/packages/pi-coding-agent/src/core/tools/bash-interceptor.test.ts
@@ -0,0 +1,198 @@
+import { describe, it } from "node:test";
+import assert from "node:assert/strict";
+import {
+	checkBashInterception,
+	compileInterceptor,
+	DEFAULT_BASH_INTERCEPTOR_RULES,
+	type BashInterceptorRule,
+} from "./bash-interceptor.js";
+
+const ALL_TOOLS = ["read", "grep", "find", "edit", "write"];
+const NO_TOOLS: string[] = [];
+
+describe("checkBashInterception", () => {
+	describe("read rule (cat/head/tail/less/more)", () => {
+		it("blocks cat with a file argument", () => {
+			const r = checkBashInterception("cat README.md", ALL_TOOLS);
+			assert.equal(r.block, true);
+			assert.equal(r.suggestedTool, "read");
+		});
+
+		it("blocks head and tail", () => {
+			assert.equal(checkBashInterception("head -n 20 file.ts", ALL_TOOLS).block, true);
+			assert.equal(checkBashInterception("tail -f app.log", ALL_TOOLS).block, true);
+		});
+
+		it("does NOT block cat used as heredoc (cat <<EOF)", () => {
+			const r = checkBashInterception("cat <<EOF > file.txt", ALL_TOOLS);
+			assert.notEqual(r.suggestedTool, "read");
+		});
+
+		it("does NOT block when read tool is absent", () => {
+			assert.equal(checkBashInterception("cat README.md", NO_TOOLS).block, false);
+			assert.equal(checkBashInterception("cat README.md", ["grep"]).block, false);
+		});
+	});
+
+	describe("grep rule", () => {
+		it("blocks grep and rg", () => {
+			assert.equal(checkBashInterception("grep foo bar.ts", ALL_TOOLS).block, true);
+			assert.equal(checkBashInterception("rg -r pattern .", ALL_TOOLS).block, true);
+		});
+
+		it("blocks grep with leading whitespace", () => {
+			assert.equal(checkBashInterception("  grep -r foo .", ALL_TOOLS).block, true);
+		});
+
+		it("does NOT block when grep tool is absent", () => {
+			assert.equal(checkBashInterception("grep foo bar", ["read", "edit"]).block, false);
+		});
+	});
+
+	describe("find rule", () => {
+		it("blocks find with -name flag", () => {
+			assert.equal(checkBashInterception('find . -name "*.ts"', ALL_TOOLS).block, true);
+		});
+
+		it("blocks find with -type flag", () => {
+			assert.equal(checkBashInterception("find /tmp -maxdepth 1 -type f", ALL_TOOLS).block, true);
+		});
+
+		it("does NOT block find without name/type flags", () => {
+			assert.equal(checkBashInterception("find /tmp -maxdepth 1", ALL_TOOLS).block, false);
+		});
+
+		it("does NOT block when find tool is absent", () => {
+			assert.equal(checkBashInterception('find . -name "*.ts"', ["read", "grep"]).block, false);
+		});
+	});
+
+	describe("edit rule (sed/perl/awk)", () => {
+		it("blocks sed -i", () => {
+			assert.equal(checkBashInterception("sed -i 's/foo/bar/' file.ts", ALL_TOOLS).block, true);
+			assert.equal(checkBashInterception("sed --in-place 's/x/y/' f", ALL_TOOLS).block, true);
+		});
+
+		it("does NOT block sed without -i (read-only)", () => {
+			assert.equal(checkBashInterception("sed 's/foo/bar/' file.ts", ALL_TOOLS).block, false);
+		});
+
+		it("blocks perl -pi and perl -p -i", () => {
+			assert.equal(checkBashInterception("perl -pi -e 's/foo/bar/' file", ALL_TOOLS).block, true);
+			assert.equal(checkBashInterception("perl -p -i -e 's/x/y/' f", ALL_TOOLS).block, true);
+		});
+
+		it("blocks awk -i inplace", () => {
+			assert.equal(checkBashInterception("awk -i inplace '{print}' file", ALL_TOOLS).block, true);
+		});
+
+		it("does NOT block when edit tool is absent", () => {
+			assert.equal(checkBashInterception("sed -i 's/a/b/' f", ["read", "grep"]).block, false);
+		});
+	});
+
+	describe("write rule (echo/printf/heredoc redirect)", () => {
+		it("blocks echo with > redirect", () => {
+			assert.equal(checkBashInterception("echo hello > file.txt", ALL_TOOLS).block, true);
+		});
+
+		it("blocks printf with > redirect", () => {
+			assert.equal(checkBashInterception('printf "%s" content > out.txt', ALL_TOOLS).block, true);
+		});
+
+		it("does NOT block echo without redirect", () => {
+			assert.equal(checkBashInterception("echo hello", ALL_TOOLS).block, false);
+		});
+
+		it("does NOT block >> append redirect (write tool does not support appending)", () => {
+			assert.equal(checkBashInterception("echo hello >> file.txt", ALL_TOOLS).block, false);
+		});
+
+		it("does NOT block stderr redirect (2>)", () => {
+			assert.equal(checkBashInterception("echo test 2> /dev/null", ALL_TOOLS).block, false);
+		});
+
+		it("does NOT block pipe (echo foo | grep bar)", () => {
+			assert.equal(checkBashInterception("echo foo | grep bar", ALL_TOOLS).block, false);
+		});
+
+		it("does NOT block when write tool is absent", () => {
+			assert.equal(checkBashInterception("echo hello > file.txt", ["read", "grep"]).block, false);
+		});
+	});
+
+	describe("pass-through commands", () => {
+		it("passes npm install", () => {
+			assert.equal(checkBashInterception("npm install", ALL_TOOLS).block, false);
+		});
+
+		it("passes ls > output.txt (not an echo/printf/cat)", () => {
+			assert.equal(checkBashInterception("ls > output.txt", ALL_TOOLS).block, false);
+		});
+
+		it("passes tee file.txt", () => {
+			assert.equal(checkBashInterception("tee file.txt", ALL_TOOLS).block, false);
+		});
+
+		it("passes git log", () => {
+			assert.equal(checkBashInterception("git log --oneline", ALL_TOOLS).block, false);
+		});
+	});
+
+	describe("block message content", () => {
+		it("includes the original command in the block message", () => {
+			const r = checkBashInterception("cat README.md", ALL_TOOLS);
+			assert.ok(r.message?.includes("cat README.md"), "message should contain original command");
+		});
+
+		it("returns block:false with no message when not blocked", () => {
+			const r = checkBashInterception("npm install", ALL_TOOLS);
+			assert.equal(r.block, false);
+			assert.equal(r.message, undefined);
+		});
+	});
+});
+
+describe("compileInterceptor", () => {
+	it("produces same results as checkBashInterception", () => {
+		const interceptor = compileInterceptor(DEFAULT_BASH_INTERCEPTOR_RULES);
+		const cases: [string, string[], boolean][] = [
+			["cat README.md", ALL_TOOLS, true],
+			["npm install", ALL_TOOLS, false],
+			["grep foo bar", ALL_TOOLS, true],
+			["echo hello >> file", ALL_TOOLS, false],
+			["echo test 2> /dev/null", ALL_TOOLS, false],
+		];
+		for (const [cmd, tools, expected] of cases) {
+			assert.equal(
+				interceptor.check(cmd, tools).block,
+				expected,
+				`pre-compiled: "${cmd}" expected block=${expected}`,
+			);
+		}
+	});
+
+	it("silently skips rules with invalid regex patterns", () => {
+		const rules: BashInterceptorRule[] = [
+			{ pattern: "[invalid(", tool: "read", message: "broken" },
+			{ pattern: "^\\s*cat\\s+", tool: "read", message: "valid" },
+		];
+		const interceptor = compileInterceptor(rules);
+		assert.equal(interceptor.check("cat file.txt", ["read"]).block, true);
+	});
+
+	it("returns block:false when available tools list is empty", () => {
+		const interceptor = compileInterceptor(DEFAULT_BASH_INTERCEPTOR_RULES);
+		assert.equal(interceptor.check("cat README.md", []).block, false);
+	});
+
+	it("allows custom rule override", () => {
+		const customRules: BashInterceptorRule[] = [
+			{ pattern: "^\\s*curl\\s+", tool: "fetch", message: "Use fetch tool instead." },
+		];
+		const interceptor = compileInterceptor(customRules);
+		assert.equal(interceptor.check("curl https://example.com", ["fetch"]).block, true);
+		// default rules not active
+		assert.equal(interceptor.check("cat file.txt", ["read"]).block, false);
+	});
+});
diff --git a/packages/pi-coding-agent/src/core/tools/bash-interceptor.ts b/packages/pi-coding-agent/src/core/tools/bash-interceptor.ts
index acf719238..309c6a10f 100644
--- a/packages/pi-coding-agent/src/core/tools/bash-interceptor.ts
+++ b/packages/pi-coding-agent/src/core/tools/bash-interceptor.ts
@@ -14,7 +14,8 @@ export interface BashInterceptorRule {
 
 export const DEFAULT_BASH_INTERCEPTOR_RULES: BashInterceptorRule[] = [
 	{
-		pattern: "^\\s*(cat|head|tail|less|more)\\s+",
+		// cat/head/tail for file viewing — excludes heredoc syntax (cat <<)
+		pattern: "^\\s*(cat(?!\\s*<<)|head|tail|less|more)\\s+",
 		tool: "read",
 		message: "Use the read tool to view file contents instead of shell commands.",
 	},
@@ -44,7 +45,9 @@ export const DEFAULT_BASH_INTERCEPTOR_RULES: BashInterceptorRule[] = [
 		message: "Use the edit tool for in-place file modifications instead of awk.",
 	},
 	{
-		pattern: "^\\s*(echo|printf|cat\\s*<<)\\s+.*[^|]>\\s*\\S",
+		// echo/printf/heredoc writing to a file via > (not >> append, not 2> stderr redirect)
+		// Matches a single > not preceded by |, >, or a digit (fd redirect like 2>)
+		pattern: "^\\s*(echo|printf|cat\\s*<<)\\s+.*(?<![|>\\d])>(?!>)\\s*\\S",
 		tool: "write",
 		message: "Use the write tool to create/overwrite files instead of shell redirects.",
 	},
@@ -56,22 +59,48 @@ export interface InterceptionResult {
 	suggestedTool?: string;
 }
 
+export interface CompiledInterceptor {
+	check: (command: string, availableTools: string[]) => InterceptionResult;
+}
+
 /**
- * Compile rules into regex objects, silently skipping invalid patterns.
+ * Compile rules into an interceptor with pre-built regex objects.
+ * Silently skips rules with invalid patterns.
+ *
+ * Pre-compiling at construction time avoids repeated `new RegExp()` calls
+ * on every bash command invocation.
  */
-function compileRules(rules: BashInterceptorRule[]): Array<{ regex: RegExp; rule: BashInterceptorRule }> {
-	return rules.flatMap((rule) => {
+export function compileInterceptor(rules: BashInterceptorRule[]): CompiledInterceptor {
+	const compiled = rules.flatMap((rule) => {
 		try {
 			return [{ regex: new RegExp(rule.pattern, rule.flags), rule }];
 		} catch {
 			return []; // skip invalid regex
 		}
 	});
+
+	return {
+		check(command: string, availableTools: string[]): InterceptionResult {
+			const trimmed = command.trim();
+			for (const { regex, rule } of compiled) {
+				if (regex.test(trimmed) && availableTools.includes(rule.tool)) {
+					return {
+						block: true,
+						message: `Blocked: ${rule.message}\n\nOriginal command: ${command}`,
+						suggestedTool: rule.tool,
+					};
+				}
+			}
+			return { block: false };
+		},
+	};
 }
 
 /**
  * Check whether a bash command should be intercepted.
  *
+ * Compiles rules on each call — prefer `compileInterceptor()` for repeated use.
+ *
  * @param command - The shell command to check
  * @param availableTools - Tool names present in the current session
  * @param rules - Override the default rule set (optional)
@@ -82,18 +111,5 @@ export function checkBashInterception(
 	rules?: BashInterceptorRule[],
 ): InterceptionResult {
 	const effectiveRules = rules ?? DEFAULT_BASH_INTERCEPTOR_RULES;
-	const compiled = compileRules(effectiveRules);
-	const trimmed = command.trim();
-
-	for (const { regex, rule } of compiled) {
-		if (regex.test(trimmed) && availableTools.includes(rule.tool)) {
-			return {
-				block: true,
-				message: `Blocked: ${rule.message}\n\nOriginal command: ${command}`,
-				suggestedTool: rule.tool,
-			};
-		}
-	}
-
-	return { block: false };
+	return compileInterceptor(effectiveRules).check(command, availableTools);
 }
diff --git a/packages/pi-coding-agent/src/core/tools/bash.ts b/packages/pi-coding-agent/src/core/tools/bash.ts
index 82e67844d..6d84199c3 100644
--- a/packages/pi-coding-agent/src/core/tools/bash.ts
+++ b/packages/pi-coding-agent/src/core/tools/bash.ts
@@ -7,7 +7,7 @@ import type { AgentTool } from "@gsd/pi-agent-core";
 import { type Static, Type } from "@sinclair/typebox";
 import { spawn } from "child_process";
 import { getShellConfig, getShellEnv, killProcessTree, sanitizeCommand } from "../../utils/shell.js";
-import { type BashInterceptorRule, checkBashInterception } from "./bash-interceptor.js";
+import { type BashInterceptorRule, compileInterceptor, DEFAULT_BASH_INTERCEPTOR_RULES } from "./bash-interceptor.js";
 import { DEFAULT_MAX_BYTES, DEFAULT_MAX_LINES, formatSize, type TruncationResult, truncateTail } from "./truncate.js";
 import type { ArtifactManager } from "../artifact-manager.js";
 
@@ -207,6 +207,12 @@ export function createBashTool(cwd: string, options?: BashToolOptions): AgentToo
 	const spawnHook = options?.spawnHook;
 	const artifactManager = options?.artifactManager;
 
+	// Pre-compile interceptor rules once at construction time
+	const interceptorInstance =
+		options?.interceptor?.enabled
+			? compileInterceptor(options.interceptor.rules ?? DEFAULT_BASH_INTERCEPTOR_RULES)
+			: null;
+
 	return {
 		name: "bash",
 		label: "bash",
@@ -219,12 +225,12 @@ export function createBashTool(cwd: string, options?: BashToolOptions): AgentToo
 			onUpdate?,
 		) => {
 			// Check bash interceptor — block commands that duplicate dedicated tools
-			if (options?.interceptor?.enabled) {
+			if (interceptorInstance) {
 				const toolNames =
-					typeof options.availableToolNames === "function"
-						? options.availableToolNames()
-						: options.availableToolNames ?? [];
-				const interception = checkBashInterception(command, toolNames, options.interceptor.rules);
+					typeof options!.availableToolNames === "function"
+						? options!.availableToolNames()
+						: options!.availableToolNames ?? [];
+				const interception = interceptorInstance.check(command, toolNames);
 				if (interception.block) {
 					return {
 						content: [{ type: "text" as const, text: interception.message ?? "Command blocked by interceptor" }],
diff --git a/packages/pi-coding-agent/src/core/tools/index.ts b/packages/pi-coding-agent/src/core/tools/index.ts
index cc3e4f891..c95fe4b78 100644
--- a/packages/pi-coding-agent/src/core/tools/index.ts
+++ b/packages/pi-coding-agent/src/core/tools/index.ts
@@ -11,6 +11,8 @@ export {
 export {
 	type BashInterceptorRule,
 	checkBashInterception,
+	type CompiledInterceptor,
+	compileInterceptor,
 	DEFAULT_BASH_INTERCEPTOR_RULES,
 	type InterceptionResult,
 } from "./bash-interceptor.js";
diff --git a/packages/pi-coding-agent/src/index.ts b/packages/pi-coding-agent/src/index.ts
index 54513d12f..4d75e487e 100644
--- a/packages/pi-coding-agent/src/index.ts
+++ b/packages/pi-coding-agent/src/index.ts
@@ -230,6 +230,8 @@ export {
 	type BashToolOptions,
 	bashTool,
 	checkBashInterception,
+	type CompiledInterceptor,
+	compileInterceptor,
 	DEFAULT_BASH_INTERCEPTOR_RULES,
 	codingTools,
 	DEFAULT_MAX_BYTES,