diff --git a/CHANGELOG.md b/CHANGELOG.md
index 20aacf256..18ef0efa6 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -27,6 +27,7 @@ Docs: https://docs.clawd.bot
 - Auto-reply: only report a model switch when session state is available. (#1465) Thanks @robbyczgw-cla.
 - Control UI: resolve local avatar URLs with basePath across injection + identity RPC. (#1457) Thanks @dlauer.
 - Agents: surface concrete API error details instead of generic AI service errors.
+- Exec approvals: allow per-segment allowlists for chained shell commands on gateway + node hosts. (#1458) Thanks @czekaj.
 - Agents: avoid sanitizing tool call IDs for OpenAI responses to preserve Pi pairing.
 - Docs: fix gog auth services example to include docs scope. (#1454) Thanks @zerone0x.
 - macOS: prefer linked channels in gateway summary to avoid false “not linked” status.
diff --git a/docs/tools/exec-approvals.md b/docs/tools/exec-approvals.md
index 6857970f6..fc657a74f 100644
--- a/docs/tools/exec-approvals.md
+++ b/docs/tools/exec-approvals.md
@@ -113,6 +113,9 @@ that can run in allowlist mode **without** explicit allowlist entries. Safe bins
 positional file args and path-like tokens, so they can only operate on the incoming stream.
 Shell chaining and redirections are not auto-allowed in allowlist mode.
 
+Shell chaining (`&&`, `||`, `;`) is allowed when every top-level segment satisfies the allowlist
+(including safe bins or skill auto-allow). Redirections remain unsupported in allowlist mode.
+
 Default safe bins: `jq`, `grep`, `cut`, `sort`, `uniq`, `head`, `tail`, `tr`, `wc`.
 
 ## Control UI editing
diff --git a/src/agents/bash-tools.exec.approval-id.test.ts b/src/agents/bash-tools.exec.approval-id.test.ts
index 651f1f4d9..16a198b5c 100644
--- a/src/agents/bash-tools.exec.approval-id.test.ts
+++ b/src/agents/bash-tools.exec.approval-id.test.ts
@@ -16,11 +16,15 @@ vi.mock("./tools/nodes-utils.js", () => ({
 
 describe("exec approvals", () => {
   let previousHome: string | undefined;
+  let previousUserProfile: string | undefined;
 
   beforeEach(async () => {
     previousHome = process.env.HOME;
+    previousUserProfile = process.env.USERPROFILE;
     const tempDir = await fs.mkdtemp(path.join(os.tmpdir(), "clawdbot-test-"));
     process.env.HOME = tempDir;
+    // Windows uses USERPROFILE for os.homedir()
+    process.env.USERPROFILE = tempDir;
   });
 
   afterEach(() => {
@@ -30,6 +34,11 @@ describe("exec approvals", () => {
     } else {
       process.env.HOME = previousHome;
     }
+    if (previousUserProfile === undefined) {
+      delete process.env.USERPROFILE;
+    } else {
+      process.env.USERPROFILE = previousUserProfile;
+    }
   });
 
   it("reuses approval id as the node runId", async () => {
diff --git a/src/agents/bash-tools.exec.ts b/src/agents/bash-tools.exec.ts
index 75f6b1927..1f102d8ab 100644
--- a/src/agents/bash-tools.exec.ts
+++ b/src/agents/bash-tools.exec.ts
@@ -10,8 +10,7 @@ import {
   type ExecSecurity,
   type ExecApprovalsFile,
   addAllowlistEntry,
-  analyzeShellCommand,
-  evaluateExecAllowlist,
+  evaluateShellAllowlist,
   maxAsk,
   minSecurity,
   requiresExecApproval,
@@ -871,9 +870,16 @@ export function createExecTool(
         if (nodeEnv) {
           applyPathPrepend(nodeEnv, defaultPathPrepend, { requireExisting: true });
         }
-        const analysis = analyzeShellCommand({ command: params.command, cwd: workdir, env });
+        const baseAllowlistEval = evaluateShellAllowlist({
+          command: params.command,
+          allowlist: [],
+          safeBins: new Set(),
+          cwd: workdir,
+          env,
+        });
+        let analysisOk = baseAllowlistEval.analysisOk;
         let allowlistSatisfied = false;
-        if (hostAsk === "on-miss" && hostSecurity === "allowlist") {
+        if (hostAsk === "on-miss" && hostSecurity === "allowlist" && analysisOk) {
           try {
             const approvalsSnapshot = (await callGatewayTool(
               "exec.approvals.node.get",
@@ -891,12 +897,15 @@ export function createExecTool(
                 overrides: { security: "allowlist" },
               });
               // Allowlist-only precheck; safe bins are node-local and may diverge.
-              allowlistSatisfied = evaluateExecAllowlist({
-                analysis,
+              const allowlistEval = evaluateShellAllowlist({
+                command: params.command,
                 allowlist: resolved.allowlist,
                 safeBins: new Set(),
                 cwd: workdir,
-              }).allowlistSatisfied;
+                env,
+              });
+              allowlistSatisfied = allowlistEval.allowlistSatisfied;
+              analysisOk = allowlistEval.analysisOk;
             }
           } catch {
             // Fall back to requiring approval if node approvals cannot be fetched.
@@ -905,7 +914,7 @@ export function createExecTool(
         const requiresAsk = requiresExecApproval({
           ask: hostAsk,
           security: hostSecurity,
-          analysisOk: analysis.ok,
+          analysisOk,
           allowlistSatisfied,
         });
         const commandText = params.command;
@@ -1095,20 +1104,21 @@ export function createExecTool(
         if (hostSecurity === "deny") {
           throw new Error("exec denied: host=gateway security=deny");
         }
-        const analysis = analyzeShellCommand({ command: params.command, cwd: workdir, env });
-        const allowlistEval = evaluateExecAllowlist({
-          analysis,
+        const allowlistEval = evaluateShellAllowlist({
+          command: params.command,
           allowlist: approvals.allowlist,
           safeBins,
           cwd: workdir,
+          env,
         });
         const allowlistMatches = allowlistEval.allowlistMatches;
+        const analysisOk = allowlistEval.analysisOk;
         const allowlistSatisfied =
-          hostSecurity === "allowlist" && analysis.ok ? allowlistEval.allowlistSatisfied : false;
+          hostSecurity === "allowlist" && analysisOk ? allowlistEval.allowlistSatisfied : false;
         const requiresAsk = requiresExecApproval({
           ask: hostAsk,
           security: hostSecurity,
-          analysisOk: analysis.ok,
+          analysisOk,
           allowlistSatisfied,
         });
 
@@ -1117,7 +1127,7 @@ export function createExecTool(
           const approvalSlug = createApprovalSlug(approvalId);
           const expiresAtMs = Date.now() + DEFAULT_APPROVAL_TIMEOUT_MS;
           const contextKey = `exec:${approvalId}`;
-          const resolvedPath = analysis.segments[0]?.resolution?.resolvedPath;
+          const resolvedPath = allowlistEval.segments[0]?.resolution?.resolvedPath;
           const noticeSeconds = Math.max(1, Math.round(approvalRunningNoticeMs / 1000));
           const commandText = params.command;
           const effectiveTimeout =
@@ -1164,7 +1174,7 @@ export function createExecTool(
               if (askFallback === "full") {
                 approvedByAsk = true;
               } else if (askFallback === "allowlist") {
-                if (!analysis.ok || !allowlistSatisfied) {
+                if (!analysisOk || !allowlistSatisfied) {
                   deniedReason = "approval-timeout (allowlist-miss)";
                 } else {
                   approvedByAsk = true;
@@ -1177,7 +1187,7 @@ export function createExecTool(
             } else if (decision === "allow-always") {
               approvedByAsk = true;
               if (hostSecurity === "allowlist") {
-                for (const segment of analysis.segments) {
+                for (const segment of allowlistEval.segments) {
                   const pattern = segment.resolution?.resolvedPath ?? "";
                   if (pattern) {
                     addAllowlistEntry(approvals.file, agentId, pattern);
@@ -1188,7 +1198,7 @@ export function createExecTool(
 
             if (
               hostSecurity === "allowlist" &&
-              (!analysis.ok || !allowlistSatisfied) &&
+              (!analysisOk || !allowlistSatisfied) &&
               !approvedByAsk
             ) {
               deniedReason = deniedReason ?? "allowlist-miss";
@@ -1288,7 +1298,7 @@ export function createExecTool(
           };
         }
 
-        if (hostSecurity === "allowlist" && (!analysis.ok || !allowlistSatisfied)) {
+        if (hostSecurity === "allowlist" && (!analysisOk || !allowlistSatisfied)) {
           throw new Error("exec denied: allowlist miss");
         }
 
@@ -1302,7 +1312,7 @@ export function createExecTool(
               agentId,
               match,
               params.command,
-              analysis.segments[0]?.resolution?.resolvedPath,
+              allowlistEval.segments[0]?.resolution?.resolvedPath,
             );
           }
         }
diff --git a/src/infra/exec-approvals.test.ts b/src/infra/exec-approvals.test.ts
index 191cc08bc..57abeb695 100644
--- a/src/infra/exec-approvals.test.ts
+++ b/src/infra/exec-approvals.test.ts
@@ -8,6 +8,7 @@ import {
   analyzeArgvCommand,
   analyzeShellCommand,
   evaluateExecAllowlist,
+  evaluateShellAllowlist,
   isSafeBinUsage,
   matchAllowlist,
   maxAsk,
@@ -121,9 +122,10 @@ describe("exec approvals shell parsing", () => {
     expect(res.segments.map((seg) => seg.argv[0])).toEqual(["echo", "jq"]);
   });
 
-  it("rejects chained commands", () => {
+  it("parses chained commands", () => {
     const res = analyzeShellCommand({ command: "ls && rm -rf /" });
-    expect(res.ok).toBe(false);
+    expect(res.ok).toBe(true);
+    expect(res.chains?.map((chain) => chain[0]?.argv[0])).toEqual(["ls", "rm"]);
   });
 
   it("parses argv commands", () => {
@@ -133,6 +135,60 @@ describe("exec approvals shell parsing", () => {
   });
 });
 
+describe("exec approvals shell allowlist (chained commands)", () => {
+  it("allows chained commands when all parts are allowlisted", () => {
+    const allowlist: ExecAllowlistEntry[] = [
+      { pattern: "/usr/bin/obsidian-cli" },
+      { pattern: "/usr/bin/head" },
+    ];
+    const result = evaluateShellAllowlist({
+      command:
+        "/usr/bin/obsidian-cli print-default && /usr/bin/obsidian-cli search foo | /usr/bin/head",
+      allowlist,
+      safeBins: new Set(),
+      cwd: "/tmp",
+    });
+    expect(result.analysisOk).toBe(true);
+    expect(result.allowlistSatisfied).toBe(true);
+  });
+
+  it("rejects chained commands when any part is not allowlisted", () => {
+    const allowlist: ExecAllowlistEntry[] = [{ pattern: "/usr/bin/obsidian-cli" }];
+    const result = evaluateShellAllowlist({
+      command: "/usr/bin/obsidian-cli print-default && /usr/bin/rm -rf /",
+      allowlist,
+      safeBins: new Set(),
+      cwd: "/tmp",
+    });
+    expect(result.analysisOk).toBe(true);
+    expect(result.allowlistSatisfied).toBe(false);
+  });
+
+  it("returns analysisOk=false for malformed chains", () => {
+    const allowlist: ExecAllowlistEntry[] = [{ pattern: "/usr/bin/echo" }];
+    const result = evaluateShellAllowlist({
+      command: "/usr/bin/echo ok &&",
+      allowlist,
+      safeBins: new Set(),
+      cwd: "/tmp",
+    });
+    expect(result.analysisOk).toBe(false);
+    expect(result.allowlistSatisfied).toBe(false);
+  });
+
+  it("respects quotes when splitting chains", () => {
+    const allowlist: ExecAllowlistEntry[] = [{ pattern: "/usr/bin/echo" }];
+    const result = evaluateShellAllowlist({
+      command: '/usr/bin/echo "foo && bar"',
+      allowlist,
+      safeBins: new Set(),
+      cwd: "/tmp",
+    });
+    expect(result.analysisOk).toBe(true);
+    expect(result.allowlistSatisfied).toBe(true);
+  });
+});
+
 describe("exec approvals safe bins", () => {
   it("allows safe bins with non-path args", () => {
     const dir = makeTempDir();
diff --git a/src/infra/exec-approvals.ts b/src/infra/exec-approvals.ts
index b2c53fc80..524a11d6b 100644
--- a/src/infra/exec-approvals.ts
+++ b/src/infra/exec-approvals.ts
@@ -506,29 +506,44 @@ export type ExecCommandAnalysis = {
   ok: boolean;
   reason?: string;
   segments: ExecCommandSegment[];
+  chains?: ExecCommandSegment[][]; // Segments grouped by chain operator (&&, ||, ;)
 };
 
-const DISALLOWED_TOKENS = new Set([";", "&", ">", "<", "`", "\n", "\r", "(", ")"]);
+const DISALLOWED_PIPELINE_TOKENS = new Set([">", "<", "`", "\n", "\r", "(", ")"]);
 
-function splitShellPipeline(command: string): { ok: boolean; reason?: string; segments: string[] } {
-  const segments: string[] = [];
+type IteratorAction = "split" | "skip" | "include" | { reject: string };
+
+/**
+ * Iterates through a command string while respecting shell quoting rules.
+ * The callback receives each character and the next character, and returns an action:
+ * - "split": push current buffer as a segment and start a new one
+ * - "skip": skip this character (and optionally the next via skip count)
+ * - "include": add this character to the buffer
+ * - { reject: reason }: abort with an error
+ */
+function iterateQuoteAware(
+  command: string,
+  onChar: (ch: string, next: string | undefined, index: number) => IteratorAction,
+): { ok: true; parts: string[]; hasSplit: boolean } | { ok: false; reason: string } {
+  const parts: string[] = [];
   let buf = "";
   let inSingle = false;
   let inDouble = false;
   let escaped = false;
+  let hasSplit = false;
 
-  const pushSegment = () => {
+  const pushPart = () => {
     const trimmed = buf.trim();
-    if (!trimmed) {
-      return false;
+    if (trimmed) {
+      parts.push(trimmed);
     }
-    segments.push(trimmed);
     buf = "";
-    return true;
   };
 
   for (let i = 0; i < command.length; i += 1) {
     const ch = command[i];
+    const next = command[i + 1];
+
     if (escaped) {
       buf += ch;
       escaped = false;
@@ -559,34 +574,66 @@ function splitShellPipeline(command: string): { ok: boolean; reason?: string; se
       buf += ch;
       continue;
     }
-    if (ch === "|" && command[i + 1] === "|") {
-      return { ok: false, reason: "unsupported shell token: ||", segments: [] };
+
+    const action = onChar(ch, next, i);
+    if (typeof action === "object" && "reject" in action) {
+      return { ok: false, reason: action.reject };
     }
-    if (ch === "|" && command[i + 1] === "&") {
-      return { ok: false, reason: "unsupported shell token: |&", segments: [] };
-    }
-    if (ch === "|") {
-      if (!pushSegment()) {
-        return { ok: false, reason: "empty pipeline segment", segments: [] };
-      }
+    if (action === "split") {
+      pushPart();
+      hasSplit = true;
       continue;
     }
-    if (DISALLOWED_TOKENS.has(ch)) {
-      return { ok: false, reason: `unsupported shell token: ${ch}`, segments: [] };
-    }
-    if (ch === "$" && command[i + 1] === "(") {
-      return { ok: false, reason: "unsupported shell token: $()", segments: [] };
+    if (action === "skip") {
+      continue;
     }
     buf += ch;
   }
 
   if (escaped || inSingle || inDouble) {
-    return { ok: false, reason: "unterminated shell quote/escape", segments: [] };
+    return { ok: false, reason: "unterminated shell quote/escape" };
   }
-  if (!pushSegment()) {
-    return { ok: false, reason: "empty command", segments: [] };
+  pushPart();
+  return { ok: true, parts, hasSplit };
+}
+
+function splitShellPipeline(command: string): { ok: boolean; reason?: string; segments: string[] } {
+  let emptySegment = false;
+  const result = iterateQuoteAware(command, (ch, next) => {
+    if (ch === "|" && next === "|") {
+      return { reject: "unsupported shell token: ||" };
+    }
+    if (ch === "|" && next === "&") {
+      return { reject: "unsupported shell token: |&" };
+    }
+    if (ch === "|") {
+      emptySegment = true;
+      return "split";
+    }
+    if (ch === "&" || ch === ";") {
+      return { reject: `unsupported shell token: ${ch}` };
+    }
+    if (DISALLOWED_PIPELINE_TOKENS.has(ch)) {
+      return { reject: `unsupported shell token: ${ch}` };
+    }
+    if (ch === "$" && next === "(") {
+      return { reject: "unsupported shell token: $()" };
+    }
+    emptySegment = false;
+    return "include";
+  });
+
+  if (!result.ok) {
+    return { ok: false, reason: result.reason, segments: [] };
   }
-  return { ok: true, segments };
+  if (emptySegment || result.parts.length === 0) {
+    return {
+      ok: false,
+      reason: result.parts.length === 0 ? "empty command" : "empty pipeline segment",
+      segments: [],
+    };
+  }
+  return { ok: true, segments: result.parts };
 }
 
 function tokenizeShellSegment(segment: string): string[] | null {
@@ -652,26 +699,61 @@ function tokenizeShellSegment(segment: string): string[] | null {
   return tokens;
 }
 
+function parseSegmentsFromParts(
+  parts: string[],
+  cwd?: string,
+  env?: NodeJS.ProcessEnv,
+): ExecCommandSegment[] | null {
+  const segments: ExecCommandSegment[] = [];
+  for (const raw of parts) {
+    const argv = tokenizeShellSegment(raw);
+    if (!argv || argv.length === 0) {
+      return null;
+    }
+    segments.push({
+      raw,
+      argv,
+      resolution: resolveCommandResolutionFromArgv(argv, cwd, env),
+    });
+  }
+  return segments;
+}
+
 export function analyzeShellCommand(params: {
   command: string;
   cwd?: string;
   env?: NodeJS.ProcessEnv;
 }): ExecCommandAnalysis {
+  // First try splitting by chain operators (&&, ||, ;)
+  const chainParts = splitCommandChain(params.command);
+  if (chainParts) {
+    const chains: ExecCommandSegment[][] = [];
+    const allSegments: ExecCommandSegment[] = [];
+
+    for (const part of chainParts) {
+      const pipelineSplit = splitShellPipeline(part);
+      if (!pipelineSplit.ok) {
+        return { ok: false, reason: pipelineSplit.reason, segments: [] };
+      }
+      const segments = parseSegmentsFromParts(pipelineSplit.segments, params.cwd, params.env);
+      if (!segments) {
+        return { ok: false, reason: "unable to parse shell segment", segments: [] };
+      }
+      chains.push(segments);
+      allSegments.push(...segments);
+    }
+
+    return { ok: true, segments: allSegments, chains };
+  }
+
+  // No chain operators, parse as simple pipeline
   const split = splitShellPipeline(params.command);
   if (!split.ok) {
     return { ok: false, reason: split.reason, segments: [] };
   }
-  const segments: ExecCommandSegment[] = [];
-  for (const raw of split.segments) {
-    const argv = tokenizeShellSegment(raw);
-    if (!argv || argv.length === 0) {
-      return { ok: false, reason: "unable to parse shell segment", segments: [] };
-    }
-    segments.push({
-      raw,
-      argv,
-      resolution: resolveCommandResolutionFromArgv(argv, params.cwd, params.env),
-    });
+  const segments = parseSegmentsFromParts(split.segments, params.cwd, params.env);
+  if (!segments) {
+    return { ok: false, reason: "unable to parse shell segment", segments: [] };
   }
   return { ok: true, segments };
 }
@@ -771,27 +853,27 @@ export type ExecAllowlistEvaluation = {
   allowlistMatches: ExecAllowlistEntry[];
 };
 
-export function evaluateExecAllowlist(params: {
-  analysis: ExecCommandAnalysis;
-  allowlist: ExecAllowlistEntry[];
-  safeBins: Set<string>;
-  cwd?: string;
-  skillBins?: Set<string>;
-  autoAllowSkills?: boolean;
-}): ExecAllowlistEvaluation {
-  const allowlistMatches: ExecAllowlistEntry[] = [];
-  if (!params.analysis.ok || params.analysis.segments.length === 0) {
-    return { allowlistSatisfied: false, allowlistMatches };
-  }
+function evaluateSegments(
+  segments: ExecCommandSegment[],
+  params: {
+    allowlist: ExecAllowlistEntry[];
+    safeBins: Set<string>;
+    cwd?: string;
+    skillBins?: Set<string>;
+    autoAllowSkills?: boolean;
+  },
+): { satisfied: boolean; matches: ExecAllowlistEntry[] } {
+  const matches: ExecAllowlistEntry[] = [];
   const allowSkills = params.autoAllowSkills === true && (params.skillBins?.size ?? 0) > 0;
-  const allowlistSatisfied = params.analysis.segments.every((segment) => {
+
+  const satisfied = segments.every((segment) => {
     const candidatePath = resolveAllowlistCandidatePath(segment.resolution, params.cwd);
     const candidateResolution =
       candidatePath && segment.resolution
         ? { ...segment.resolution, resolvedPath: candidatePath }
         : segment.resolution;
     const match = matchAllowlist(params.allowlist, candidateResolution);
-    if (match) allowlistMatches.push(match);
+    if (match) matches.push(match);
     const safe = isSafeBinUsage({
       argv: segment.argv,
       resolution: segment.resolution,
@@ -804,7 +886,230 @@ export function evaluateExecAllowlist(params: {
         : false;
     return Boolean(match || safe || skillAllow);
   });
-  return { allowlistSatisfied, allowlistMatches };
+
+  return { satisfied, matches };
+}
+
+export function evaluateExecAllowlist(params: {
+  analysis: ExecCommandAnalysis;
+  allowlist: ExecAllowlistEntry[];
+  safeBins: Set<string>;
+  cwd?: string;
+  skillBins?: Set<string>;
+  autoAllowSkills?: boolean;
+}): ExecAllowlistEvaluation {
+  const allowlistMatches: ExecAllowlistEntry[] = [];
+  if (!params.analysis.ok || params.analysis.segments.length === 0) {
+    return { allowlistSatisfied: false, allowlistMatches };
+  }
+
+  // If the analysis contains chains, evaluate each chain part separately
+  if (params.analysis.chains) {
+    for (const chainSegments of params.analysis.chains) {
+      const result = evaluateSegments(chainSegments, {
+        allowlist: params.allowlist,
+        safeBins: params.safeBins,
+        cwd: params.cwd,
+        skillBins: params.skillBins,
+        autoAllowSkills: params.autoAllowSkills,
+      });
+      if (!result.satisfied) {
+        return { allowlistSatisfied: false, allowlistMatches: [] };
+      }
+      allowlistMatches.push(...result.matches);
+    }
+    return { allowlistSatisfied: true, allowlistMatches };
+  }
+
+  // No chains, evaluate all segments together
+  const result = evaluateSegments(params.analysis.segments, {
+    allowlist: params.allowlist,
+    safeBins: params.safeBins,
+    cwd: params.cwd,
+    skillBins: params.skillBins,
+    autoAllowSkills: params.autoAllowSkills,
+  });
+  return { allowlistSatisfied: result.satisfied, allowlistMatches: result.matches };
+}
+
+/**
+ * Splits a command string by chain operators (&&, ||, ;) while respecting quotes.
+ * Returns null when no chain is present or when the chain is malformed.
+ */
+function splitCommandChain(command: string): string[] | null {
+  const parts: string[] = [];
+  let buf = "";
+  let inSingle = false;
+  let inDouble = false;
+  let escaped = false;
+  let foundChain = false;
+  let invalidChain = false;
+
+  const pushPart = () => {
+    const trimmed = buf.trim();
+    if (trimmed) {
+      parts.push(trimmed);
+      buf = "";
+      return true;
+    }
+    buf = "";
+    return false;
+  };
+
+  for (let i = 0; i < command.length; i += 1) {
+    const ch = command[i];
+    if (escaped) {
+      buf += ch;
+      escaped = false;
+      continue;
+    }
+    if (!inSingle && !inDouble && ch === "\\") {
+      escaped = true;
+      buf += ch;
+      continue;
+    }
+    if (inSingle) {
+      if (ch === "'") inSingle = false;
+      buf += ch;
+      continue;
+    }
+    if (inDouble) {
+      if (ch === '"') inDouble = false;
+      buf += ch;
+      continue;
+    }
+    if (ch === "'") {
+      inSingle = true;
+      buf += ch;
+      continue;
+    }
+    if (ch === '"') {
+      inDouble = true;
+      buf += ch;
+      continue;
+    }
+
+    if (ch === "&" && command[i + 1] === "&") {
+      if (!pushPart()) invalidChain = true;
+      i += 1;
+      foundChain = true;
+      continue;
+    }
+    if (ch === "|" && command[i + 1] === "|") {
+      if (!pushPart()) invalidChain = true;
+      i += 1;
+      foundChain = true;
+      continue;
+    }
+    if (ch === ";") {
+      if (!pushPart()) invalidChain = true;
+      foundChain = true;
+      continue;
+    }
+
+    buf += ch;
+  }
+
+  const pushedFinal = pushPart();
+  if (!foundChain) return null;
+  if (invalidChain || !pushedFinal) return null;
+  return parts.length > 0 ? parts : null;
+}
+
+export type ExecAllowlistAnalysis = {
+  analysisOk: boolean;
+  allowlistSatisfied: boolean;
+  allowlistMatches: ExecAllowlistEntry[];
+  segments: ExecCommandSegment[];
+};
+
+/**
+ * Evaluates allowlist for shell commands (including &&, ||, ;) and returns analysis metadata.
+ */
+export function evaluateShellAllowlist(params: {
+  command: string;
+  allowlist: ExecAllowlistEntry[];
+  safeBins: Set<string>;
+  cwd?: string;
+  env?: NodeJS.ProcessEnv;
+  skillBins?: Set<string>;
+  autoAllowSkills?: boolean;
+}): ExecAllowlistAnalysis {
+  const chainParts = splitCommandChain(params.command);
+  if (!chainParts) {
+    const analysis = analyzeShellCommand({
+      command: params.command,
+      cwd: params.cwd,
+      env: params.env,
+    });
+    if (!analysis.ok) {
+      return {
+        analysisOk: false,
+        allowlistSatisfied: false,
+        allowlistMatches: [],
+        segments: [],
+      };
+    }
+    const evaluation = evaluateExecAllowlist({
+      analysis,
+      allowlist: params.allowlist,
+      safeBins: params.safeBins,
+      cwd: params.cwd,
+      skillBins: params.skillBins,
+      autoAllowSkills: params.autoAllowSkills,
+    });
+    return {
+      analysisOk: true,
+      allowlistSatisfied: evaluation.allowlistSatisfied,
+      allowlistMatches: evaluation.allowlistMatches,
+      segments: analysis.segments,
+    };
+  }
+
+  const allowlistMatches: ExecAllowlistEntry[] = [];
+  const segments: ExecCommandSegment[] = [];
+
+  for (const part of chainParts) {
+    const analysis = analyzeShellCommand({
+      command: part,
+      cwd: params.cwd,
+      env: params.env,
+    });
+    if (!analysis.ok) {
+      return {
+        analysisOk: false,
+        allowlistSatisfied: false,
+        allowlistMatches: [],
+        segments: [],
+      };
+    }
+
+    segments.push(...analysis.segments);
+    const evaluation = evaluateExecAllowlist({
+      analysis,
+      allowlist: params.allowlist,
+      safeBins: params.safeBins,
+      cwd: params.cwd,
+      skillBins: params.skillBins,
+      autoAllowSkills: params.autoAllowSkills,
+    });
+    allowlistMatches.push(...evaluation.allowlistMatches);
+    if (!evaluation.allowlistSatisfied) {
+      return {
+        analysisOk: true,
+        allowlistSatisfied: false,
+        allowlistMatches,
+        segments,
+      };
+    }
+  }
+
+  return {
+    analysisOk: true,
+    allowlistSatisfied: true,
+    allowlistMatches,
+    segments,
+  };
 }
 
 export function requiresExecApproval(params: {
diff --git a/src/node-host/runner.ts b/src/node-host/runner.ts
index a66aa63f1..1274d83a5 100644
--- a/src/node-host/runner.ts
+++ b/src/node-host/runner.ts
@@ -6,8 +6,8 @@ import path from "node:path";
 import {
   addAllowlistEntry,
   analyzeArgvCommand,
-  analyzeShellCommand,
   evaluateExecAllowlist,
+  evaluateShellAllowlist,
   requiresExecApproval,
   normalizeExecApprovals,
   recordAllowlistUse,
@@ -18,6 +18,8 @@ import {
   resolveExecApprovalsSocketPath,
   saveExecApprovals,
   type ExecApprovalsFile,
+  type ExecAllowlistEntry,
+  type ExecCommandSegment,
 } from "../infra/exec-approvals.js";
 import {
   requestExecHostViaSocket,
@@ -585,24 +587,45 @@ async function handleInvoke(
   const sessionKey = params.sessionKey?.trim() || "node";
   const runId = params.runId?.trim() || crypto.randomUUID();
   const env = sanitizeEnv(params.env ?? undefined);
-  const analysis = rawCommand
-    ? analyzeShellCommand({ command: rawCommand, cwd: params.cwd ?? undefined, env })
-    : analyzeArgvCommand({ argv, cwd: params.cwd ?? undefined, env });
   const cfg = loadConfig();
   const agentExec = agentId ? resolveAgentConfig(cfg, agentId)?.tools?.exec : undefined;
   const safeBins = resolveSafeBins(agentExec?.safeBins ?? cfg.tools?.exec?.safeBins);
   const bins = autoAllowSkills ? await skillBins.current() : new Set<string>();
-  const allowlistEval = evaluateExecAllowlist({
-    analysis,
-    allowlist: approvals.allowlist,
-    safeBins,
-    cwd: params.cwd ?? undefined,
-    skillBins: bins,
-    autoAllowSkills,
-  });
-  const allowlistMatches = allowlistEval.allowlistMatches;
-  const allowlistSatisfied =
-    security === "allowlist" && analysis.ok ? allowlistEval.allowlistSatisfied : false;
+  let analysisOk = false;
+  let allowlistMatches: ExecAllowlistEntry[] = [];
+  let allowlistSatisfied = false;
+  let segments: ExecCommandSegment[] = [];
+  if (rawCommand) {
+    const allowlistEval = evaluateShellAllowlist({
+      command: rawCommand,
+      allowlist: approvals.allowlist,
+      safeBins,
+      cwd: params.cwd ?? undefined,
+      env,
+      skillBins: bins,
+      autoAllowSkills,
+    });
+    analysisOk = allowlistEval.analysisOk;
+    allowlistMatches = allowlistEval.allowlistMatches;
+    allowlistSatisfied =
+      security === "allowlist" && analysisOk ? allowlistEval.allowlistSatisfied : false;
+    segments = allowlistEval.segments;
+  } else {
+    const analysis = analyzeArgvCommand({ argv, cwd: params.cwd ?? undefined, env });
+    const allowlistEval = evaluateExecAllowlist({
+      analysis,
+      allowlist: approvals.allowlist,
+      safeBins,
+      cwd: params.cwd ?? undefined,
+      skillBins: bins,
+      autoAllowSkills,
+    });
+    analysisOk = analysis.ok;
+    allowlistMatches = allowlistEval.allowlistMatches;
+    allowlistSatisfied =
+      security === "allowlist" && analysisOk ? allowlistEval.allowlistSatisfied : false;
+    segments = analysis.segments;
+  }
 
   const useMacAppExec = process.platform === "darwin";
   if (useMacAppExec) {
@@ -709,7 +732,7 @@ async function handleInvoke(
   const requiresAsk = requiresExecApproval({
     ask,
     security,
-    analysisOk: analysis.ok,
+    analysisOk,
     allowlistSatisfied,
   });
 
@@ -737,15 +760,15 @@ async function handleInvoke(
     return;
   }
   if (approvalDecision === "allow-always" && security === "allowlist") {
-    if (analysis.ok) {
-      for (const segment of analysis.segments) {
+    if (analysisOk) {
+      for (const segment of segments) {
         const pattern = segment.resolution?.resolvedPath ?? "";
         if (pattern) addAllowlistEntry(approvals.file, agentId, pattern);
       }
     }
   }
 
-  if (security === "allowlist" && (!analysis.ok || !allowlistSatisfied) && !approvedByAsk) {
+  if (security === "allowlist" && (!analysisOk || !allowlistSatisfied) && !approvedByAsk) {
     await sendNodeEvent(
       client,
       "exec.denied",
@@ -774,7 +797,7 @@ async function handleInvoke(
         agentId,
         match,
         cmdText,
-        analysis.segments[0]?.resolution?.resolvedPath,
+        segments[0]?.resolution?.resolvedPath,
       );
     }
   }