diff --git a/CHANGELOG.md b/CHANGELOG.md
index b495fb798bb..f486b910056 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -35,6 +35,7 @@ Docs: https://docs.openclaw.ai
 - 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/exec approvals: treat backslash-newline as shell line continuation during macOS shell-chain parsing so line-continued `$(` substitutions fail closed instead of slipping past command-substitution checks.
+- Security/exec approvals: bind macOS skill auto-allow trust to both executable name and resolved path so same-basename binaries no longer inherit trust from unrelated skill bins.
 - 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/ExecApprovalEvaluation.swift b/apps/macos/Sources/OpenClaw/ExecApprovalEvaluation.swift
index c7d9d0928e1..a36e58db1d8 100644
--- a/apps/macos/Sources/OpenClaw/ExecApprovalEvaluation.swift
+++ b/apps/macos/Sources/OpenClaw/ExecApprovalEvaluation.swift
@@ -45,8 +45,8 @@ enum ExecApprovalEvaluator {
 
         let skillAllow: Bool
         if approvals.agent.autoAllowSkills, !allowlistResolutions.isEmpty {
-            let bins = await SkillBinsCache.shared.currentBins()
-            skillAllow = allowlistResolutions.allSatisfy { bins.contains($0.executableName) }
+            let bins = await SkillBinsCache.shared.currentTrust()
+            skillAllow = self.isSkillAutoAllowed(allowlistResolutions, trustedBinsByName: bins)
         } else {
             skillAllow = false
         }
@@ -65,4 +65,26 @@ enum ExecApprovalEvaluator {
             allowlistMatch: allowlistSatisfied ? allowlistMatches.first : nil,
             skillAllow: skillAllow)
     }
+
+    static func isSkillAutoAllowed(
+        _ resolutions: [ExecCommandResolution],
+        trustedBinsByName: [String: Set<String>]) -> Bool
+    {
+        guard !resolutions.isEmpty, !trustedBinsByName.isEmpty else { return false }
+        return resolutions.allSatisfy { resolution in
+            guard let executableName = SkillBinsCache.normalizeSkillBinName(resolution.executableName),
+                  let resolvedPath = SkillBinsCache.normalizeResolvedPath(resolution.resolvedPath)
+            else {
+                return false
+            }
+            return trustedBinsByName[executableName]?.contains(resolvedPath) == true
+        }
+    }
+
+    static func _testIsSkillAutoAllowed(
+        _ resolutions: [ExecCommandResolution],
+        trustedBinsByName: [String: Set<String>]) -> Bool
+    {
+        self.isSkillAutoAllowed(resolutions, trustedBinsByName: trustedBinsByName)
+    }
 }
diff --git a/apps/macos/Sources/OpenClaw/ExecApprovals.swift b/apps/macos/Sources/OpenClaw/ExecApprovals.swift
index ba49b37cd9f..7fc4385b96c 100644
--- a/apps/macos/Sources/OpenClaw/ExecApprovals.swift
+++ b/apps/macos/Sources/OpenClaw/ExecApprovals.swift
@@ -777,6 +777,7 @@ actor SkillBinsCache {
     static let shared = SkillBinsCache()
 
     private var bins: Set<String> = []
+    private var trustByName: [String: Set<String>] = [:]
     private var lastRefresh: Date?
     private let refreshInterval: TimeInterval = 90
 
@@ -787,27 +788,90 @@ actor SkillBinsCache {
         return self.bins
     }
 
+    func currentTrust(force: Bool = false) async -> [String: Set<String>] {
+        if force || self.isStale() {
+            await self.refresh()
+        }
+        return self.trustByName
+    }
+
     func refresh() async {
         do {
             let report = try await GatewayConnection.shared.skillsStatus()
-            var next = Set<String>()
-            for skill in report.skills {
-                for bin in skill.requirements.bins {
-                    let trimmed = bin.trimmingCharacters(in: .whitespacesAndNewlines)
-                    if !trimmed.isEmpty { next.insert(trimmed) }
-                }
-            }
-            self.bins = next
+            let trust = Self.buildTrustIndex(report: report, searchPaths: CommandResolver.preferredPaths())
+            self.bins = trust.names
+            self.trustByName = trust.pathsByName
             self.lastRefresh = Date()
         } catch {
             if self.lastRefresh == nil {
                 self.bins = []
+                self.trustByName = [:]
             }
         }
     }
 
+    static func normalizeSkillBinName(_ value: String) -> String? {
+        let trimmed = value.trimmingCharacters(in: .whitespacesAndNewlines).lowercased()
+        return trimmed.isEmpty ? nil : trimmed
+    }
+
+    static func normalizeResolvedPath(_ value: String?) -> String? {
+        let trimmed = value?.trimmingCharacters(in: .whitespacesAndNewlines) ?? ""
+        guard !trimmed.isEmpty else { return nil }
+        return URL(fileURLWithPath: trimmed).standardizedFileURL.path
+    }
+
+    static func buildTrustIndex(
+        report: SkillsStatusReport,
+        searchPaths: [String]) -> SkillBinTrustIndex
+    {
+        var names = Set<String>()
+        var pathsByName: [String: Set<String>] = [:]
+
+        for skill in report.skills {
+            for bin in skill.requirements.bins {
+                let trimmed = bin.trimmingCharacters(in: .whitespacesAndNewlines)
+                guard !trimmed.isEmpty else { continue }
+                names.insert(trimmed)
+
+                guard let name = self.normalizeSkillBinName(trimmed),
+                      let resolvedPath = self.resolveSkillBinPath(trimmed, searchPaths: searchPaths),
+                      let normalizedPath = self.normalizeResolvedPath(resolvedPath)
+                else {
+                    continue
+                }
+
+                var paths = pathsByName[name] ?? Set<String>()
+                paths.insert(normalizedPath)
+                pathsByName[name] = paths
+            }
+        }
+
+        return SkillBinTrustIndex(names: names, pathsByName: pathsByName)
+    }
+
+    private static func resolveSkillBinPath(_ bin: String, searchPaths: [String]) -> String? {
+        let expanded = bin.hasPrefix("~") ? (bin as NSString).expandingTildeInPath : bin
+        if expanded.contains("/") || expanded.contains("\\") {
+            return FileManager().isExecutableFile(atPath: expanded) ? expanded : nil
+        }
+        return CommandResolver.findExecutable(named: expanded, searchPaths: searchPaths)
+    }
+
     private func isStale() -> Bool {
         guard let lastRefresh else { return true }
         return Date().timeIntervalSince(lastRefresh) > self.refreshInterval
     }
+
+    static func _testBuildTrustIndex(
+        report: SkillsStatusReport,
+        searchPaths: [String]) -> SkillBinTrustIndex
+    {
+        self.buildTrustIndex(report: report, searchPaths: searchPaths)
+    }
+}
+
+struct SkillBinTrustIndex {
+    let names: Set<String>
+    let pathsByName: [String: Set<String>]
 }
diff --git a/apps/macos/Tests/OpenClawIPCTests/ExecSkillBinTrustTests.swift b/apps/macos/Tests/OpenClawIPCTests/ExecSkillBinTrustTests.swift
new file mode 100644
index 00000000000..779b59a3499
--- /dev/null
+++ b/apps/macos/Tests/OpenClawIPCTests/ExecSkillBinTrustTests.swift
@@ -0,0 +1,90 @@
+import Foundation
+import Testing
+@testable import OpenClaw
+
+struct ExecSkillBinTrustTests {
+    @Test func `build trust index resolves skill bin paths`() throws {
+        let fixture = try Self.makeExecutable(named: "jq")
+        defer { try? FileManager.default.removeItem(at: fixture.root) }
+
+        let trust = SkillBinsCache._testBuildTrustIndex(
+            report: Self.makeReport(bins: ["jq"]),
+            searchPaths: [fixture.root.path])
+
+        #expect(trust.names == ["jq"])
+        #expect(trust.pathsByName["jq"] == [fixture.path])
+    }
+
+    @Test func `skill auto allow accepts trusted resolved skill bin path`() throws {
+        let fixture = try Self.makeExecutable(named: "jq")
+        defer { try? FileManager.default.removeItem(at: fixture.root) }
+
+        let trust = SkillBinsCache._testBuildTrustIndex(
+            report: Self.makeReport(bins: ["jq"]),
+            searchPaths: [fixture.root.path])
+        let resolution = ExecCommandResolution(
+            rawExecutable: "jq",
+            resolvedPath: fixture.path,
+            executableName: "jq",
+            cwd: nil)
+
+        #expect(ExecApprovalEvaluator._testIsSkillAutoAllowed([resolution], trustedBinsByName: trust.pathsByName))
+    }
+
+    @Test func `skill auto allow rejects same basename at different path`() throws {
+        let trusted = try Self.makeExecutable(named: "jq")
+        let untrusted = try Self.makeExecutable(named: "jq")
+        defer {
+            try? FileManager.default.removeItem(at: trusted.root)
+            try? FileManager.default.removeItem(at: untrusted.root)
+        }
+
+        let trust = SkillBinsCache._testBuildTrustIndex(
+            report: Self.makeReport(bins: ["jq"]),
+            searchPaths: [trusted.root.path])
+        let resolution = ExecCommandResolution(
+            rawExecutable: "jq",
+            resolvedPath: untrusted.path,
+            executableName: "jq",
+            cwd: nil)
+
+        #expect(!ExecApprovalEvaluator._testIsSkillAutoAllowed([resolution], trustedBinsByName: trust.pathsByName))
+    }
+
+    private static func makeExecutable(named name: String) throws -> (root: URL, path: String) {
+        let root = FileManager.default.temporaryDirectory
+            .appendingPathComponent("openclaw-skill-bin-\(UUID().uuidString)", isDirectory: true)
+        try FileManager.default.createDirectory(at: root, withIntermediateDirectories: true)
+        let file = root.appendingPathComponent(name)
+        try "#!/bin/sh\nexit 0\n".write(to: file, atomically: true, encoding: .utf8)
+        try FileManager.default.setAttributes(
+            [.posixPermissions: NSNumber(value: Int16(0o755))],
+            ofItemAtPath: file.path)
+        return (root, file.path)
+    }
+
+    private static func makeReport(bins: [String]) -> SkillsStatusReport {
+        SkillsStatusReport(
+            workspaceDir: "/tmp/workspace",
+            managedSkillsDir: "/tmp/skills",
+            skills: [
+                SkillStatus(
+                    name: "test-skill",
+                    description: "test",
+                    source: "local",
+                    filePath: "/tmp/skills/test-skill/SKILL.md",
+                    baseDir: "/tmp/skills/test-skill",
+                    skillKey: "test-skill",
+                    primaryEnv: nil,
+                    emoji: nil,
+                    homepage: nil,
+                    always: false,
+                    disabled: false,
+                    eligible: true,
+                    requirements: SkillRequirements(bins: bins, env: [], config: []),
+                    missing: SkillMissing(bins: [], env: [], config: []),
+                    configChecks: [],
+                    install: [])
+            ])
+    }
+}