diff --git a/src/core/auto-approval/__tests__/commands.spec.ts b/src/core/auto-approval/__tests__/commands.spec.ts
index 90d2808ba9c..cccb34a7c64 100644
--- a/src/core/auto-approval/__tests__/commands.spec.ts
+++ b/src/core/auto-approval/__tests__/commands.spec.ts
@@ -1,4 +1,9 @@
-import { containsDangerousSubstitution, getCommandDecision } from "../commands"
+import {
+	containsDangerousSubstitution,
+	getCommandDecision,
+	findLongestPrefixMatch,
+	isAutoApprovedSingleCommand,
+} from "../commands"
 
 describe("containsDangerousSubstitution", () => {
 	describe("zsh array assignments (should NOT be flagged)", () => {
@@ -99,3 +104,70 @@ describe("getCommandDecision — integration with dangerous substitution checks"
 		expect(getCommandDecision('echo "${var@P}"', allowedCommands)).toBe("ask_user")
 	})
 })
+
+describe("findLongestPrefixMatch — trailing wildcard support", () => {
+	it("should match 'git*' against 'git commit -m \"Fix nav bar\"'", () => {
+		expect(findLongestPrefixMatch('git commit -m "Fix nav bar"', ["git*"])).toBe("git*")
+	})
+
+	it("should match 'git *' against 'git commit' but not 'gitk'", () => {
+		// "git *" normalizes to "git " (with trailing space)
+		expect(findLongestPrefixMatch("git commit", ["git *"])).toBe("git *")
+		expect(findLongestPrefixMatch("gitk", ["git *"])).toBeNull()
+	})
+
+	it("should match 'git*' against 'gitk' (no space required)", () => {
+		expect(findLongestPrefixMatch("gitk", ["git*"])).toBe("git*")
+	})
+
+	it("should strip multiple trailing asterisks", () => {
+		expect(findLongestPrefixMatch("git status", ["git**"])).toBe("git**")
+	})
+
+	it("should prefer a longer trailing-wildcard prefix over a shorter one", () => {
+		expect(findLongestPrefixMatch("git push origin", ["git*", "git push*"])).toBe("git push*")
+	})
+
+	it("should prefer a specific trailing-wildcard prefix over standalone '*'", () => {
+		expect(findLongestPrefixMatch("git status", ["*", "git*"])).toBe("git*")
+	})
+
+	it("should still match standalone '*' when no other prefix matches", () => {
+		expect(findLongestPrefixMatch("unknown command", ["*", "git*"])).toBe("*")
+	})
+
+	it("should return null when no prefix matches and no wildcard present", () => {
+		expect(findLongestPrefixMatch("npm install", ["git*"])).toBeNull()
+	})
+})
+
+describe("isAutoApprovedSingleCommand — trailing wildcard support", () => {
+	it("should auto-approve 'git commit -m ...' when allowedCommands has 'git*'", () => {
+		expect(isAutoApprovedSingleCommand('git commit -m "Fix dark mode"', ["git*"])).toBe(true)
+	})
+
+	it("should not auto-approve 'npm install' when allowedCommands has 'git*'", () => {
+		expect(isAutoApprovedSingleCommand("npm install", ["git*"])).toBe(false)
+	})
+
+	it("should auto-approve 'git commit' with 'git *' but not 'gitk'", () => {
+		expect(isAutoApprovedSingleCommand("git commit", ["git *"])).toBe(true)
+		expect(isAutoApprovedSingleCommand("gitk", ["git *"])).toBe(false)
+	})
+})
+
+describe("getCommandDecision — trailing wildcard with deny list", () => {
+	it("should auto-approve 'git status' with 'git*' in allowlist", () => {
+		expect(getCommandDecision("git status", ["git*"], [])).toBe("auto_approve")
+	})
+
+	it("should deny 'git push' when denied and allowed with equal-length prefixes", () => {
+		// "git*" (length 4) vs "git push" (length 8) in denylist -> deny wins (longer)
+		expect(getCommandDecision("git push origin", ["git*"], ["git push"])).toBe("auto_deny")
+	})
+
+	it("should approve 'git status' when denied prefix is less specific", () => {
+		// "git status*" (length 11) vs "git*" (length 4) in denylist -> allow wins (longer)
+		expect(getCommandDecision("git status", ["git status*"], ["git*"])).toBe("auto_approve")
+	})
+})
diff --git a/src/core/auto-approval/commands.ts b/src/core/auto-approval/commands.ts
index d9e88c7ba26..2334601cb0b 100644
--- a/src/core/auto-approval/commands.ts
+++ b/src/core/auto-approval/commands.ts
@@ -99,13 +99,30 @@ export function findLongestPrefixMatch(command: string, prefixes: string[]): str
 
 	const trimmedCommand = command.trim().toLowerCase()
 	let longestMatch: string | null = null
+	let longestMatchLength = 0
 
 	for (const prefix of prefixes) {
 		const lowerPrefix = prefix.toLowerCase()
-		// Handle wildcard "*" - it matches any command
-		if (lowerPrefix === "*" || trimmedCommand.startsWith(lowerPrefix)) {
-			if (!longestMatch || lowerPrefix.length > longestMatch.length) {
+
+		// Handle standalone wildcard "*" - it matches any command
+		if (lowerPrefix === "*") {
+			if (!longestMatch) {
+				longestMatch = lowerPrefix
+				longestMatchLength = 1
+			}
+			continue
+		}
+
+		// Strip trailing asterisk(s) to support trailing-wildcard patterns
+		// e.g. "git*" -> "git", "git *" -> "git " (note the space is preserved)
+		const normalizedPrefix = lowerPrefix.replace(/\*+$/, "")
+
+		if (trimmedCommand.startsWith(normalizedPrefix)) {
+			// Use the original prefix length for comparison so that
+			// "git*" (4 chars) beats a standalone "*" (1 char)
+			if (lowerPrefix.length > longestMatchLength) {
 				longestMatch = lowerPrefix
+				longestMatchLength = lowerPrefix.length
 			}
 		}
 	}
@@ -145,7 +162,10 @@ export function isAutoApprovedSingleCommand(
 		return allowedCommands.some((prefix) => {
 			const lowerPrefix = prefix.toLowerCase()
 			// Handle wildcard "*" - it matches any command
-			return lowerPrefix === "*" || trimmedCommand.startsWith(lowerPrefix)
+			if (lowerPrefix === "*") return true
+			// Strip trailing asterisk(s) to support trailing-wildcard patterns
+			const normalizedPrefix = lowerPrefix.replace(/\*+$/, "")
+			return trimmedCommand.startsWith(normalizedPrefix)
 		})
 	}
 
diff --git a/webview-ui/src/i18n/locales/en/settings.json b/webview-ui/src/i18n/locales/en/settings.json
index 3b2497aaee7..5ad2609bcb8 100644
--- a/webview-ui/src/i18n/locales/en/settings.json
+++ b/webview-ui/src/i18n/locales/en/settings.json
@@ -327,7 +327,7 @@
 			"label": "Execute",
 			"description": "Automatically execute allowed terminal commands without requiring approval",
 			"allowedCommands": "Allowed Auto-Execute Commands",
-			"allowedCommandsDescription": "Command prefixes that can be auto-executed when \"Always approve execute operations\" is enabled. Add * to allow all commands (use with caution).",
+			"allowedCommandsDescription": "Command prefixes that can be auto-executed when \"Always approve execute operations\" is enabled. For example, \"git\" matches all git commands. Trailing wildcards like \"git*\" are also supported. Add * to allow all commands (use with caution).",
 			"deniedCommands": "Denied Commands",
 			"deniedCommandsDescription": "Command prefixes that will be automatically denied without asking for approval. In case of conflicts with allowed commands, the longest prefix match takes precedence. Add * to deny all commands.",
 			"commandPlaceholder": "Enter command prefix (e.g., 'git ')",