diff --git a/webview-ui/src/utils/__tests__/commandPatterns.spec.ts b/webview-ui/src/utils/__tests__/commandPatterns.spec.ts
index 783c0d6215..15dbab5e0f 100644
--- a/webview-ui/src/utils/__tests__/commandPatterns.spec.ts
+++ b/webview-ui/src/utils/__tests__/commandPatterns.spec.ts
@@ -117,6 +117,243 @@ describe("extractCommandPatterns", () => {
 			expect(patterns).toEqual(["git", "git add", "git status"])
 		})
 	})
+
+	describe("complex real-world examples", () => {
+		it("should correctly parse unzip with pipe chain", () => {
+			const command = "unzip -l builds/roo-cline-3.21.5-error-boundary-component.vsix|grep map"
+			const patterns = extractCommandPatterns(command)
+
+			// Should extract individual commands from the chain
+			expect(patterns).toContain("unzip")
+			expect(patterns).toContain("grep")
+
+			// Should not include the full chain
+			expect(patterns).not.toContain(command)
+
+			// Should not include flags or arguments
+			expect(patterns).not.toContain("unzip -l")
+			expect(patterns).not.toContain("grep map")
+		})
+
+		it("should correctly parse git push with multiple arguments", () => {
+			const command = "git push github refactor-use-files-for-history -f"
+			const patterns = extractCommandPatterns(command)
+
+			// Should extract base command and subcommand
+			expect(patterns).toContain("git")
+			expect(patterns).toContain("git push")
+
+			// Should not include remote, branch, or flags
+			expect(patterns).not.toContain("git push github")
+			expect(patterns).not.toContain("github")
+			expect(patterns).not.toContain("refactor-use-files-for-history")
+			expect(patterns).not.toContain("-f")
+		})
+
+		it("should correctly parse complex build and install chain", () => {
+			const command =
+				"../roo-main/build.sh && code --install-extension builds/roo-cline-3.21.5-error-boundary-component.vsix && code"
+			const patterns = extractCommandPatterns(command)
+
+			// Should extract script file
+			expect(patterns).toContain("../roo-main/build.sh")
+
+			// Should extract code command (appears twice, but set will dedupe)
+			expect(patterns).toContain("code")
+
+			// Should not include the full chain
+			expect(patterns).not.toContain(command)
+
+			// Should not include flags or arguments
+			expect(patterns).not.toContain("code --install-extension")
+			expect(patterns).not.toContain("--install-extension")
+			expect(patterns).not.toContain("builds/roo-cline-3.21.5-error-boundary-component.vsix")
+		})
+
+		it("should handle npm scripts with arguments", () => {
+			const command = "npm run build -- --watch"
+			const patterns = extractCommandPatterns(command)
+
+			expect(patterns).toContain("npm")
+			expect(patterns).toContain("npm run")
+			// Should stop at 'run' to allow any script
+			expect(patterns).not.toContain("npm run build")
+		})
+
+		it("should handle docker commands with subcommands", () => {
+			const command = "docker compose up -d"
+			const patterns = extractCommandPatterns(command)
+
+			expect(patterns).toContain("docker")
+			expect(patterns).toContain("docker compose")
+			expect(patterns).not.toContain("docker compose up")
+			expect(patterns).not.toContain("-d")
+		})
+
+		it("should handle kubectl commands", () => {
+			const command = "kubectl get pods -n production"
+			const patterns = extractCommandPatterns(command)
+
+			expect(patterns).toContain("kubectl")
+			expect(patterns).toContain("kubectl get")
+			expect(patterns).not.toContain("kubectl get pods")
+			expect(patterns).not.toContain("-n")
+			expect(patterns).not.toContain("production")
+		})
+
+		it("should handle make targets", () => {
+			const command = "make clean && make build"
+			const patterns = extractCommandPatterns(command)
+
+			expect(patterns).toContain("make")
+			expect(patterns).toContain("make clean")
+			expect(patterns).toContain("make build")
+		})
+
+		it("should handle python scripts with arguments", () => {
+			const command = "python3 scripts/deploy.py --env production"
+			const patterns = extractCommandPatterns(command)
+
+			expect(patterns).toContain("python3")
+			// Should stop after interpreter
+			expect(patterns).not.toContain("scripts/deploy.py")
+			expect(patterns).not.toContain("--env")
+		})
+
+		it("should handle environment variables with commands", () => {
+			const command = "NODE_ENV=test npm test && NODE_ENV=production npm start"
+			const patterns = extractCommandPatterns(command)
+
+			expect(patterns).toContain("npm")
+			expect(patterns).toContain("npm test")
+			expect(patterns).toContain("npm start")
+			expect(patterns).not.toContain("NODE_ENV=test")
+			expect(patterns).not.toContain("NODE_ENV=production")
+		})
+
+		it("should handle complex pipe with multiple tools", () => {
+			const command = "ps aux | grep node | awk '{print $2}' | xargs kill -9"
+			const patterns = extractCommandPatterns(command)
+
+			expect(patterns).toContain("ps")
+			expect(patterns).toContain("grep")
+			expect(patterns).toContain("awk")
+			expect(patterns).toContain("xargs")
+			// Note: "xargs kill -9" is parsed as a single command where xargs is the command
+			// and "kill -9" are arguments, so kill is not extracted as a separate pattern
+			expect(patterns).not.toContain("kill")
+			expect(patterns).not.toContain("ps aux")
+			expect(patterns).not.toContain("grep node")
+			expect(patterns).not.toContain("kill -9")
+		})
+
+		it("should handle yarn workspaces commands", () => {
+			const command = "yarn workspace @myapp/frontend build"
+			const patterns = extractCommandPatterns(command)
+
+			expect(patterns).toContain("yarn")
+			expect(patterns).toContain("yarn workspace")
+			// Should not include the workspace name
+			expect(patterns).not.toContain("@myapp/frontend")
+			expect(patterns).not.toContain("build")
+		})
+
+		it("should handle pnpm commands", () => {
+			const command = "pnpm --filter ./packages/* test"
+			const patterns = extractCommandPatterns(command)
+
+			expect(patterns).toContain("pnpm")
+			// Should stop at flags
+			expect(patterns).not.toContain("pnpm --filter")
+			expect(patterns).not.toContain("test")
+		})
+
+		it("should handle curl with complex arguments", () => {
+			const command =
+				"curl -X POST https://api.example.com/data -H 'Content-Type: application/json' -d '{\"key\": \"value\"}'"
+			const patterns = extractCommandPatterns(command)
+
+			expect(patterns).toContain("curl")
+			// Should stop at flags
+			expect(patterns).not.toContain("curl -X")
+			expect(patterns).not.toContain("POST")
+			expect(patterns).not.toContain("https://api.example.com/data")
+		})
+
+		it("should handle ssh commands", () => {
+			const command = "ssh user@server.com 'cd /app && npm restart'"
+			const patterns = extractCommandPatterns(command)
+
+			expect(patterns).toContain("ssh")
+			// Should not include user@server or remote command
+			expect(patterns).not.toContain("user@server.com")
+			expect(patterns).not.toContain("cd")
+			expect(patterns).not.toContain("npm")
+		})
+
+		it("should handle rsync commands", () => {
+			const command = "rsync -avz --delete ./dist/ user@server:/var/www/html/"
+			const patterns = extractCommandPatterns(command)
+
+			expect(patterns).toContain("rsync")
+			// Should stop at flags
+			expect(patterns).not.toContain("rsync -avz")
+			expect(patterns).not.toContain("--delete")
+		})
+
+		it("should handle find with exec", () => {
+			const command = "find . -name '*.log' -exec rm {} \\;"
+			const patterns = extractCommandPatterns(command)
+
+			expect(patterns).toContain("find")
+			// Should not include dangerous operations
+			expect(patterns).not.toContain("rm")
+			expect(patterns).not.toContain("-exec")
+		})
+
+		it("should handle systemctl commands", () => {
+			const command = "sudo systemctl restart nginx"
+			const patterns = extractCommandPatterns(command)
+
+			expect(patterns).toContain("sudo")
+			// Note: sudo is the command, systemctl is treated as an argument
+			// The parser doesn't have special handling for sudo to extract the actual command
+			expect(patterns).not.toContain("systemctl")
+			expect(patterns).not.toContain("nginx")
+		})
+
+		it("should handle aws cli commands", () => {
+			const command = "aws s3 sync ./build s3://my-bucket --delete"
+			const patterns = extractCommandPatterns(command)
+
+			expect(patterns).toContain("aws")
+			// aws is not in special handling, so behavior may vary
+			expect(patterns).not.toContain("--delete")
+		})
+
+		it("should handle multiple redirects", () => {
+			const command = "echo 'test' > file.txt && cat file.txt >> output.log"
+			const patterns = extractCommandPatterns(command)
+
+			expect(patterns).toContain("echo")
+			expect(patterns).toContain("cat")
+			expect(patterns).not.toContain("echo 'test'")
+			expect(patterns).not.toContain("file.txt")
+			expect(patterns).not.toContain("output.log")
+		})
+
+		it("should handle background processes", () => {
+			const command = "npm start & npm run worker &"
+			const patterns = extractCommandPatterns(command)
+
+			expect(patterns).toContain("npm")
+			expect(patterns).toContain("npm start")
+			// Note: The & operator is not in the chainOperators list (only &&, ||, ;, |)
+			// So this is parsed as a single command "npm start & npm run worker &"
+			// The parser stops at the first & character when parsing "npm start &..."
+			expect(patterns).not.toContain("npm run")
+		})
+	})
 })
 
 describe("getPatternDescription", () => {