diff --git a/Fluid.xcodeproj/project.pbxproj b/Fluid.xcodeproj/project.pbxproj
index d72a6a01..2264c7c2 100644
--- a/Fluid.xcodeproj/project.pbxproj
+++ b/Fluid.xcodeproj/project.pbxproj
@@ -12,6 +12,7 @@
 		7C3697892ED70F9C005874CE /* DynamicNotchKit in Frameworks */ = {isa = PBXBuildFile; productRef = 7C3697882ED70F9C005874CE /* DynamicNotchKit */; };
 		7C5AF14B2F15041600DE21B0 /* MediaRemoteAdapter in Frameworks */ = {isa = PBXBuildFile; productRef = 7C5AF14A2F15041600DE21B0 /* MediaRemoteAdapter */; };
 		7C91B0012F42AA0100C0DEF0 /* HotkeyShortcutTests.swift in Sources */ = {isa = PBXBuildFile; fileRef = 7C91B0022F42AA0100C0DEF0 /* HotkeyShortcutTests.swift */; };
+		7227748E55EEC815B29C9CDA /* CommandModeDestructiveCommandTests.swift in Sources */ = {isa = PBXBuildFile; fileRef = AE848A4EF5AF955BAD08708B /* CommandModeDestructiveCommandTests.swift */; };
 		7CDB0A2D2F3C4D5600FB7CAD /* DictationE2ETests.swift in Sources */ = {isa = PBXBuildFile; fileRef = 7CDB0A292F3C4D5600FB7CAD /* DictationE2ETests.swift */; };
 		7CDB0A2E2F3C4D5600FB7CAD /* AudioFixtureLoader.swift in Sources */ = {isa = PBXBuildFile; fileRef = 7CDB0A2A2F3C4D5600FB7CAD /* AudioFixtureLoader.swift */; };
 		7CDB0A2F2F3C4D5600FB7CAD /* dictation_fixture.wav in Resources */ = {isa = PBXBuildFile; fileRef = 7CDB0A2B2F3C4D5600FB7CAD /* dictation_fixture.wav */; };
@@ -33,6 +34,7 @@
 		7C078D8F2E3B339200FB7CAC /* FluidVoice Debug.app */ = {isa = PBXFileReference; explicitFileType = wrapper.application; includeInIndex = 0; path = "FluidVoice Debug.app"; sourceTree = BUILT_PRODUCTS_DIR; };
 		7CDB0A202F3C4D5600FB7CAD /* FluidDictationIntegrationTests.xctest */ = {isa = PBXFileReference; explicitFileType = wrapper.cfbundle; includeInIndex = 0; path = FluidDictationIntegrationTests.xctest; sourceTree = BUILT_PRODUCTS_DIR; };
 		7C91B0022F42AA0100C0DEF0 /* HotkeyShortcutTests.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = HotkeyShortcutTests.swift; sourceTree = "<group>"; };
+		AE848A4EF5AF955BAD08708B /* CommandModeDestructiveCommandTests.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = CommandModeDestructiveCommandTests.swift; sourceTree = "<group>"; };
 		7CDB0A292F3C4D5600FB7CAD /* DictationE2ETests.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = DictationE2ETests.swift; sourceTree = "<group>"; };
 		7CDB0A2A2F3C4D5600FB7CAD /* AudioFixtureLoader.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = AudioFixtureLoader.swift; sourceTree = "<group>"; };
 		7CDB0A2B2F3C4D5600FB7CAD /* dictation_fixture.wav */ = {isa = PBXFileReference; lastKnownFileType = audio.wav; path = dictation_fixture.wav; sourceTree = "<group>"; };
@@ -104,6 +106,7 @@
 				7CDB0A272F3C4D5600FB7CAD /* Resources */,
 				7CDB0A292F3C4D5600FB7CAD /* DictationE2ETests.swift */,
 				7C91B0022F42AA0100C0DEF0 /* HotkeyShortcutTests.swift */,
+				AE848A4EF5AF955BAD08708B /* CommandModeDestructiveCommandTests.swift */,
 			);
 			path = FluidDictationIntegrationTests;
 			sourceTree = "<group>";
@@ -258,6 +261,7 @@
 				7CDB0A2E2F3C4D5600FB7CAD /* AudioFixtureLoader.swift in Sources */,
 				7CDB0A2D2F3C4D5600FB7CAD /* DictationE2ETests.swift in Sources */,
 				7C91B0012F42AA0100C0DEF0 /* HotkeyShortcutTests.swift in Sources */,
+				7227748E55EEC815B29C9CDA /* CommandModeDestructiveCommandTests.swift in Sources */,
 			);
 			runOnlyForDeploymentPostprocessing = 0;
 		};
diff --git a/Sources/Fluid/Services/CommandModeService.swift b/Sources/Fluid/Services/CommandModeService.swift
index b356788c..5d557843 100644
--- a/Sources/Fluid/Services/CommandModeService.swift
+++ b/Sources/Fluid/Services/CommandModeService.swift
@@ -432,7 +432,7 @@ final class CommandModeService: ObservableObject {
                 }
 
                 // Check if we need confirmation for destructive commands
-                if SettingsStore.shared.commandModeConfirmBeforeExecute, self.isDestructiveCommand(tc.command) {
+                if SettingsStore.shared.commandModeConfirmBeforeExecute, Self.isDestructiveCommand(tc.command) {
                     self.didRequireConfirmationThisRun = true
                     self.pendingCommand = PendingCommand(
                         id: tc.id,
@@ -591,8 +591,28 @@ final class CommandModeService: ObservableObject {
         }
     }
 
-    private func isDestructiveCommand(_ command: String) -> Bool {
-        let cmd = command.lowercased()
+    nonisolated static func isDestructiveCommand(_ command: String) -> Bool {
+        // Inspect each chained segment independently so a destructive command
+        // hidden after a separator (for example "echo ok && killall Finder")
+        // is not masked by a benign leading command. "&&", "||", ";", "&"
+        // (background) and newlines all separate commands in the shell. Pipe
+        // ("|") is intentionally not a split point here; piped destructive
+        // commands are matched by the substring patterns in isDestructiveSegment.
+        // "&&" is normalized before the single "&" so it is not mistaken for two
+        // background separators.
+        let normalized = command
+            .replacingOccurrences(of: "&&", with: "\n")
+            .replacingOccurrences(of: "||", with: "\n")
+            .replacingOccurrences(of: ";", with: "\n")
+            .replacingOccurrences(of: "&", with: "\n")
+
+        return normalized
+            .components(separatedBy: "\n")
+            .contains { isDestructiveSegment($0.trimmingCharacters(in: .whitespaces)) }
+    }
+
+    private nonisolated static func isDestructiveSegment(_ segment: String) -> Bool {
+        let cmd = segment.lowercased()
 
         // Commands that start with these are destructive
         let destructivePrefixes = [
diff --git a/Tests/FluidDictationIntegrationTests/CommandModeDestructiveCommandTests.swift b/Tests/FluidDictationIntegrationTests/CommandModeDestructiveCommandTests.swift
new file mode 100644
index 00000000..29137bc6
--- /dev/null
+++ b/Tests/FluidDictationIntegrationTests/CommandModeDestructiveCommandTests.swift
@@ -0,0 +1,70 @@
+@testable import FluidVoice_Debug
+import XCTest
+
+final class CommandModeDestructiveCommandTests: XCTestCase {
+    // MARK: - Chained separators hide a destructive command
+
+    func testAndSeparatorHidesDestructiveCommand() {
+        XCTAssertTrue(CommandModeService.isDestructiveCommand("echo ok && killall Finder"))
+    }
+
+    func testSemicolonSeparatorHidesDestructiveCommand() {
+        XCTAssertTrue(CommandModeService.isDestructiveCommand("true; shred secret.txt"))
+    }
+
+    func testOrSeparatorHidesDestructiveCommand() {
+        XCTAssertTrue(CommandModeService.isDestructiveCommand("echo a || killall Finder"))
+    }
+
+    func testNewlineSeparatorHidesDestructiveCommand() {
+        XCTAssertTrue(CommandModeService.isDestructiveCommand("echo hi\nsudo reboot"))
+    }
+
+    func testBackgroundSeparatorHidesDestructiveCommand() {
+        XCTAssertTrue(CommandModeService.isDestructiveCommand("echo ok & killall Finder"))
+    }
+
+    func testOrSeparatorWithRemoveIsDetected() {
+        XCTAssertTrue(CommandModeService.isDestructiveCommand("foo || rm bar"))
+    }
+
+    func testTrailingSegmentDeepInChainIsDetected() {
+        XCTAssertTrue(CommandModeService.isDestructiveCommand("cd /tmp && echo hi && sudo rm -rf /"))
+    }
+
+    // MARK: - Safe chains stay allowed
+
+    func testSafeAndChainIsAllowed() {
+        XCTAssertFalse(CommandModeService.isDestructiveCommand("cd /tmp && ls"))
+    }
+
+    func testSafeSemicolonChainIsAllowed() {
+        XCTAssertFalse(CommandModeService.isDestructiveCommand("echo a; echo b"))
+    }
+
+    func testBackgroundedSafeCommandIsAllowed() {
+        XCTAssertFalse(CommandModeService.isDestructiveCommand("sleep 10 & echo done"))
+    }
+
+    // MARK: - Existing single-command detection is preserved
+
+    func testSingleRemoveCommandIsDetected() {
+        XCTAssertTrue(CommandModeService.isDestructiveCommand("rm -rf /tmp/foo"))
+    }
+
+    func testSingleSudoCommandIsDetected() {
+        XCTAssertTrue(CommandModeService.isDestructiveCommand("sudo reboot"))
+    }
+
+    func testSingleKillallCommandIsDetected() {
+        XCTAssertTrue(CommandModeService.isDestructiveCommand("killall Finder"))
+    }
+
+    func testPipedDestructiveCommandIsDetected() {
+        XCTAssertTrue(CommandModeService.isDestructiveCommand("cat foo | rm bar"))
+    }
+
+    func testSafeSingleCommandIsAllowed() {
+        XCTAssertFalse(CommandModeService.isDestructiveCommand("ls -la"))
+    }
+}