diff --git a/CHANGELOG.md b/CHANGELOG.md
index 688f7edd549..378abe860fa 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -33,6 +33,7 @@ Docs: https://docs.openclaw.ai
 - Security/exec approvals: unwrap more `pnpm` runtime forms during approval binding, including `pnpm --reporter ... exec` and direct `pnpm node` file runs, with matching regression coverage and docs updates.
 - Security/exec approvals: fail closed for Perl `-M` and `-I` approval flows so preload and load-path module resolution stays outside approval-backed runtime execution unless the operator uses a broader explicit trust path.
 - Security/exec approvals: recognize PowerShell `-File` and `-f` wrapper forms during inline-command extraction so approval and command-analysis paths treat file-based PowerShell launches like the existing `-Command` variants.
+- Security/exec approvals: unwrap `env` dispatch wrappers inside shell-segment allowlist resolution on macOS so `env FOO=bar /path/to/bin` resolves against the effective executable instead of the wrapper token.
 - Security/external content: strip zero-width and soft-hyphen marker-splitting characters during boundary sanitization so spoofed `EXTERNAL_UNTRUSTED_CONTENT` markers fall back to the existing hardening path instead of bypassing marker normalization.
 - Control UI/insecure auth: preserve explicit shared token and password auth on plain-HTTP Control UI connects so LAN and reverse-proxy sessions no longer drop shared auth before the first WebSocket handshake. (#45088) Thanks @velvet-shark.
 - macOS/onboarding: avoid self-restarting freshly bootstrapped launchd gateways and give new daemon installs longer to become healthy, so `openclaw onboard --install-daemon` no longer false-fails on slower Macs and fresh VM snapshots.
diff --git a/apps/macos/Sources/OpenClaw/ExecCommandResolution.swift b/apps/macos/Sources/OpenClaw/ExecCommandResolution.swift
index 91a22153f3c..ff5d360baea 100644
--- a/apps/macos/Sources/OpenClaw/ExecCommandResolution.swift
+++ b/apps/macos/Sources/OpenClaw/ExecCommandResolution.swift
@@ -37,8 +37,7 @@ struct ExecCommandResolution {
             var resolutions: [ExecCommandResolution] = []
             resolutions.reserveCapacity(segments.count)
             for segment in segments {
-                guard let token = self.parseFirstToken(segment),
-                      let resolution = self.resolveExecutable(rawExecutable: token, cwd: cwd, env: env)
+                guard let resolution = self.resolveShellSegmentExecutable(segment, cwd: cwd, env: env)
                 else {
                     return []
                 }
@@ -88,6 +87,20 @@ struct ExecCommandResolution {
             cwd: cwd)
     }
 
+    private static func resolveShellSegmentExecutable(
+        _ segment: String,
+        cwd: String?,
+        env: [String: String]?) -> ExecCommandResolution?
+    {
+        let tokens = self.tokenizeShellWords(segment)
+        guard !tokens.isEmpty else { return nil }
+        let effective = ExecEnvInvocationUnwrapper.unwrapDispatchWrappersForResolution(tokens)
+        guard let raw = effective.first?.trimmingCharacters(in: .whitespacesAndNewlines), !raw.isEmpty else {
+            return nil
+        }
+        return self.resolveExecutable(rawExecutable: raw, cwd: cwd, env: env)
+    }
+
     private static func parseFirstToken(_ command: String) -> String? {
         let trimmed = command.trimmingCharacters(in: .whitespacesAndNewlines)
         guard !trimmed.isEmpty else { return nil }
@@ -102,6 +115,59 @@ struct ExecCommandResolution {
         return trimmed.split(whereSeparator: { $0.isWhitespace }).first.map(String.init)
     }
 
+    private static func tokenizeShellWords(_ command: String) -> [String] {
+        let trimmed = command.trimmingCharacters(in: .whitespacesAndNewlines)
+        guard !trimmed.isEmpty else { return [] }
+
+        var tokens: [String] = []
+        var current = ""
+        var inSingle = false
+        var inDouble = false
+        var escaped = false
+
+        func appendCurrent() {
+            guard !current.isEmpty else { return }
+            tokens.append(current)
+            current.removeAll(keepingCapacity: true)
+        }
+
+        for ch in trimmed {
+            if escaped {
+                current.append(ch)
+                escaped = false
+                continue
+            }
+
+            if ch == "\\", !inSingle {
+                escaped = true
+                continue
+            }
+
+            if ch == "'", !inDouble {
+                inSingle.toggle()
+                continue
+            }
+
+            if ch == "\"", !inSingle {
+                inDouble.toggle()
+                continue
+            }
+
+            if ch.isWhitespace, !inSingle, !inDouble {
+                appendCurrent()
+                continue
+            }
+
+            current.append(ch)
+        }
+
+        if escaped {
+            current.append("\\")
+        }
+        appendCurrent()
+        return tokens
+    }
+
     private enum ShellTokenContext {
         case unquoted
         case doubleQuoted
diff --git a/apps/macos/Tests/OpenClawIPCTests/ExecAllowlistTests.swift b/apps/macos/Tests/OpenClawIPCTests/ExecAllowlistTests.swift
index f12b8f717dc..efe23213b99 100644
--- a/apps/macos/Tests/OpenClawIPCTests/ExecAllowlistTests.swift
+++ b/apps/macos/Tests/OpenClawIPCTests/ExecAllowlistTests.swift
@@ -208,6 +208,30 @@ struct ExecAllowlistTests {
         #expect(resolutions[1].executableName == "touch")
     }
 
+    @Test func `resolve for allowlist unwraps env dispatch wrappers inside shell segments`() {
+        let command = ["/bin/sh", "-lc", "env /usr/bin/touch /tmp/openclaw-allowlist-test"]
+        let resolutions = ExecCommandResolution.resolveForAllowlist(
+            command: command,
+            rawCommand: "env /usr/bin/touch /tmp/openclaw-allowlist-test",
+            cwd: nil,
+            env: ["PATH": "/usr/bin:/bin"])
+        #expect(resolutions.count == 1)
+        #expect(resolutions[0].resolvedPath == "/usr/bin/touch")
+        #expect(resolutions[0].executableName == "touch")
+    }
+
+    @Test func `resolve for allowlist unwraps env assignments inside shell segments`() {
+        let command = ["/bin/sh", "-lc", "env FOO=bar /usr/bin/touch /tmp/openclaw-allowlist-test"]
+        let resolutions = ExecCommandResolution.resolveForAllowlist(
+            command: command,
+            rawCommand: "env FOO=bar /usr/bin/touch /tmp/openclaw-allowlist-test",
+            cwd: nil,
+            env: ["PATH": "/usr/bin:/bin"])
+        #expect(resolutions.count == 1)
+        #expect(resolutions[0].resolvedPath == "/usr/bin/touch")
+        #expect(resolutions[0].executableName == "touch")
+    }
+
     @Test func `resolve for allowlist unwraps env to effective direct executable`() {
         let command = ["/usr/bin/env", "FOO=bar", "/usr/bin/printf", "ok"]
         let resolutions = ExecCommandResolution.resolveForAllowlist(