diff --git a/src/cli/args.ts b/src/cli/args.ts
index d056c3e..7123dbf 100644
--- a/src/cli/args.ts
+++ b/src/cli/args.ts
@@ -271,14 +271,34 @@ export const CLI_FLAG_CATALOG = {
   "max-turns": { parser: { type: "string" }, mode: "headless" },
 } as const satisfies Record<string, CliFlagDefinition>;
 
+type CliFlagCatalog = typeof CLI_FLAG_CATALOG;
+
+type CliCatalogOptionDescriptors = {
+  [K in keyof CliFlagCatalog]: CliFlagCatalog[K]["parser"];
+};
+
+type CliParsedValueForDescriptor<Descriptor extends CliFlagParserConfig> =
+  Descriptor["type"] extends "boolean"
+    ? Descriptor["multiple"] extends true
+      ? boolean[]
+      : boolean
+    : Descriptor["multiple"] extends true
+      ? string[]
+      : string;
+
+export type CliParsedValues = {
+  [K in keyof CliCatalogOptionDescriptors]?: CliParsedValueForDescriptor<
+    CliCatalogOptionDescriptors[K]
+  >;
+};
+
 const CLI_FLAG_ENTRIES = Object.entries(CLI_FLAG_CATALOG) as Array<
-  [string, CliFlagDefinition]
+  [keyof CliFlagCatalog, CliFlagDefinition]
 >;
 
-export const CLI_OPTIONS: Record<string, CliFlagParserConfig> =
-  Object.fromEntries(
-    CLI_FLAG_ENTRIES.map(([name, definition]) => [name, definition.parser]),
-  );
+export const CLI_OPTIONS = Object.fromEntries(
+  CLI_FLAG_ENTRIES.map(([name, definition]) => [name, definition.parser]),
+) as CliCatalogOptionDescriptors;
 // Column width for left-aligned flag labels in generated --help output.
 const HELP_LABEL_WIDTH = 24;
 
@@ -334,12 +354,16 @@ export function preprocessCliArgs(args: string[]): string[] {
 }
 
 export function parseCliArgs(args: string[], strict: boolean) {
-  return parseArgs({
+  const parsed = parseArgs({
     args,
     options: CLI_OPTIONS,
     strict,
     allowPositionals: true,
   });
+  return {
+    ...parsed,
+    values: parsed.values as CliParsedValues,
+  };
 }
 
 export type ParsedCliArgs = ReturnType<typeof parseCliArgs>;
diff --git a/src/headless.ts b/src/headless.ts
index bb048a5..ea2b62e 100644
--- a/src/headless.ts
+++ b/src/headless.ts
@@ -151,11 +151,11 @@ type ReflectionOverrides = {
 };
 
 function parseReflectionOverrides(
-  values: Record<string, unknown>,
+  values: ParsedCliArgs["values"],
 ): ReflectionOverrides {
-  const triggerRaw = values["reflection-trigger"] as string | undefined;
-  const behaviorRaw = values["reflection-behavior"] as string | undefined;
-  const stepCountRaw = values["reflection-step-count"] as string | undefined;
+  const triggerRaw = values["reflection-trigger"];
+  const behaviorRaw = values["reflection-behavior"];
+  const stepCountRaw = values["reflection-step-count"];
 
   if (!triggerRaw && !behaviorRaw && !stepCountRaw) {
     return {};
@@ -275,11 +275,11 @@ export async function handleHeadlessCommand(
   // Set tool filter if provided (controls which tools are loaded)
   if (values.tools !== undefined) {
     const { toolFilter } = await import("./tools/filter");
-    toolFilter.setEnabledTools(values.tools as string);
+    toolFilter.setEnabledTools(values.tools);
   }
   // Set permission mode if provided (or via --yolo alias)
-  const permissionModeValue = values["permission-mode"] as string | undefined;
-  const yoloMode = values.yolo as boolean | undefined;
+  const permissionModeValue = values["permission-mode"];
+  const yoloMode = values.yolo;
   if (yoloMode || permissionModeValue) {
     const { permissionMode } = await import("./permissions/mode");
     if (yoloMode) {
@@ -307,15 +307,15 @@ export async function handleHeadlessCommand(
   if (values.allowedTools || values.disallowedTools) {
     const { cliPermissions } = await import("./permissions/cli");
     if (values.allowedTools) {
-      cliPermissions.setAllowedTools(values.allowedTools as string);
+      cliPermissions.setAllowedTools(values.allowedTools);
     }
     if (values.disallowedTools) {
-      cliPermissions.setDisallowedTools(values.disallowedTools as string);
+      cliPermissions.setDisallowedTools(values.disallowedTools);
     }
   }
 
   // Check for input-format early - if stream-json, we don't need a prompt
-  const inputFormat = values["input-format"] as string | undefined;
+  const inputFormat = values["input-format"];
   const isBidirectionalMode = inputFormat === "stream-json";
 
   // If headless output is being piped and the downstream closes early (e.g.
@@ -372,38 +372,35 @@ export async function handleHeadlessCommand(
   }
 
   // --new: Create a new conversation (for concurrent sessions)
-  let forceNewConversation = (values.new as boolean | undefined) ?? false;
-  const fromAgentId = values["from-agent"] as string | undefined;
+  let forceNewConversation = values.new ?? false;
+  const fromAgentId = values["from-agent"];
 
   // Resolve agent (same logic as interactive mode)
   let agent: AgentState | null = null;
-  let specifiedAgentId = values.agent as string | undefined;
-  const specifiedAgentName = values.name as string | undefined;
-  let specifiedConversationId = values.conversation as string | undefined;
-  const shouldContinue = values.continue as boolean | undefined;
-  const forceNew = values["new-agent"] as boolean | undefined;
-  const systemPromptPreset = values.system as string | undefined;
-  const systemCustom = values["system-custom"] as string | undefined;
-  const systemAppend = values["system-append"] as string | undefined;
-  const embeddingModel = values.embedding as string | undefined;
-  const memoryBlocksJson = values["memory-blocks"] as string | undefined;
-  const blockValueArgs = values["block-value"] as string[] | undefined;
-  const initBlocksRaw = values["init-blocks"] as string | undefined;
-  const baseToolsRaw = values["base-tools"] as string | undefined;
-  const skillsDirectory =
-    (values.skills as string | undefined) ?? skillsDirectoryOverride;
-  const noSkillsFlag = values["no-skills"] as boolean | undefined;
-  const noBundledSkillsFlag = values["no-bundled-skills"] as
-    | boolean
-    | undefined;
-  const skillSourcesRaw = values["skill-sources"] as string | undefined;
-  const memfsFlag = values.memfs as boolean | undefined;
-  const noMemfsFlag = values["no-memfs"] as boolean | undefined;
+  let specifiedAgentId = values.agent;
+  const specifiedAgentName = values.name;
+  let specifiedConversationId = values.conversation;
+  const shouldContinue = values.continue;
+  const forceNew = values["new-agent"];
+  const systemPromptPreset = values.system;
+  const systemCustom = values["system-custom"];
+  const systemAppend = values["system-append"];
+  const embeddingModel = values.embedding;
+  const memoryBlocksJson = values["memory-blocks"];
+  const blockValueArgs = values["block-value"];
+  const initBlocksRaw = values["init-blocks"];
+  const baseToolsRaw = values["base-tools"];
+  const skillsDirectory = values.skills ?? skillsDirectoryOverride;
+  const noSkillsFlag = values["no-skills"];
+  const noBundledSkillsFlag = values["no-bundled-skills"];
+  const skillSourcesRaw = values["skill-sources"];
+  const memfsFlag = values.memfs;
+  const noMemfsFlag = values["no-memfs"];
   // Startup policy for the git-backed memory pull on session init.
   // "blocking" (default): await the pull before proceeding.
   // "background": fire the pull async, emit init without waiting.
   // "skip": skip the pull entirely this session.
-  const memfsStartupRaw = values["memfs-startup"] as string | undefined;
+  const memfsStartupRaw = values["memfs-startup"];
   const memfsStartupPolicy: "blocking" | "background" | "skip" =
     memfsStartupRaw === "background" || memfsStartupRaw === "skip"
       ? memfsStartupRaw
@@ -415,13 +412,12 @@ export async function handleHeadlessCommand(
       : undefined;
   const shouldAutoEnableMemfsForNewAgent = !memfsFlag && !noMemfsFlag;
   const fromAfFile = resolveImportFlagAlias({
-    importFlagValue: values.import as string | undefined,
-    fromAfFlagValue: values["from-af"] as string | undefined,
+    importFlagValue: values.import,
+    fromAfFlagValue: values["from-af"],
   });
-  const preLoadSkillsRaw = values["pre-load-skills"] as string | undefined;
+  const preLoadSkillsRaw = values["pre-load-skills"];
   const systemInfoReminderEnabled =
-    systemInfoReminderEnabledOverride ??
-    !(values["no-system-info-reminder"] as boolean | undefined);
+    systemInfoReminderEnabledOverride ?? !values["no-system-info-reminder"];
   const reflectionOverrides = (() => {
     try {
       return parseReflectionOverrides(values);
@@ -432,8 +428,8 @@ export async function handleHeadlessCommand(
       process.exit(1);
     }
   })();
-  const maxTurnsRaw = values["max-turns"] as string | undefined;
-  const tagsRaw = values.tags as string | undefined;
+  const maxTurnsRaw = values["max-turns"];
+  const tagsRaw = values.tags;
   const resolvedSkillSources = (() => {
     if (skillSourcesOverride) {
       return skillSourcesOverride;
@@ -1098,8 +1094,7 @@ export async function handleHeadlessCommand(
   setAgentContext(agent.id, skillsDirectory, resolvedSkillSources);
 
   // Validate output format
-  const outputFormat =
-    (values["output-format"] as string | undefined) || "text";
+  const outputFormat = values["output-format"] || "text";
   const includePartialMessages = Boolean(values["include-partial-messages"]);
   if (!["text", "json", "stream-json"].includes(outputFormat)) {
     console.error(
diff --git a/src/index.ts b/src/index.ts
index 056a566..e2b7f10 100755
--- a/src/index.ts
+++ b/src/index.ts
@@ -443,19 +443,18 @@ async function main(): Promise<void> {
   }
 
   // --continue: Resume last session (agent + conversation) automatically
-  const shouldContinue = (values.continue as boolean | undefined) ?? false;
+  const shouldContinue = values.continue ?? false;
   // --resume: Open agent selector UI after loading
-  const shouldResume = (values.resume as boolean | undefined) ?? false;
-  let specifiedConversationId =
-    (values.conversation as string | undefined) ?? null; // Specific conversation to resume
-  const forceNew = (values["new-agent"] as boolean | undefined) ?? false;
+  const shouldResume = values.resume ?? false;
+  let specifiedConversationId = values.conversation ?? null; // Specific conversation to resume
+  const forceNew = values["new-agent"] ?? false;
 
   // --new: Create a new conversation (for concurrent sessions)
-  const forceNewConversation = (values.new as boolean | undefined) ?? false;
+  const forceNewConversation = values.new ?? false;
 
-  const initBlocksRaw = values["init-blocks"] as string | undefined;
-  const baseToolsRaw = values["base-tools"] as string | undefined;
-  let specifiedAgentId = (values.agent as string | undefined) ?? null;
+  const initBlocksRaw = values["init-blocks"];
+  const baseToolsRaw = values["base-tools"];
+  let specifiedAgentId = values.agent ?? null;
   try {
     const normalized = normalizeConversationShorthandFlags({
       specifiedConversationId,
@@ -486,32 +485,26 @@ async function main(): Promise<void> {
     process.exit(1);
   }
 
-  const specifiedAgentName = (values.name as string | undefined) ?? null;
-  const specifiedModel = (values.model as string | undefined) ?? undefined;
-  const systemPromptPreset = (values.system as string | undefined) ?? undefined;
-  const systemCustom =
-    (values["system-custom"] as string | undefined) ?? undefined;
+  const specifiedAgentName = values.name ?? null;
+  const specifiedModel = values.model ?? undefined;
+  const systemPromptPreset = values.system ?? undefined;
+  const systemCustom = values["system-custom"] ?? undefined;
   // Note: systemAppend is also parsed but only used in headless mode (headless.ts handles it)
-  const memoryBlocksJson =
-    (values["memory-blocks"] as string | undefined) ?? undefined;
-  const specifiedToolset = (values.toolset as string | undefined) ?? undefined;
-  const skillsDirectory = (values.skills as string | undefined) ?? undefined;
-  const memfsFlag = values.memfs as boolean | undefined;
-  const noMemfsFlag = values["no-memfs"] as boolean | undefined;
+  const memoryBlocksJson = values["memory-blocks"] ?? undefined;
+  const specifiedToolset = values.toolset ?? undefined;
+  const skillsDirectory = values.skills ?? undefined;
+  const memfsFlag = values.memfs;
+  const noMemfsFlag = values["no-memfs"];
   const requestedMemoryPromptMode: "memfs" | "standard" | undefined = memfsFlag
     ? "memfs"
     : noMemfsFlag
       ? "standard"
       : undefined;
   const shouldAutoEnableMemfsForNewAgent = !memfsFlag && !noMemfsFlag;
-  const noSkillsFlag = values["no-skills"] as boolean | undefined;
-  const noBundledSkillsFlag = values["no-bundled-skills"] as
-    | boolean
-    | undefined;
-  const skillSourcesRaw = values["skill-sources"] as string | undefined;
-  const noSystemInfoReminderFlag = values["no-system-info-reminder"] as
-    | boolean
-    | undefined;
+  const noSkillsFlag = values["no-skills"];
+  const noBundledSkillsFlag = values["no-bundled-skills"];
+  const skillSourcesRaw = values["skill-sources"];
+  const noSystemInfoReminderFlag = values["no-system-info-reminder"];
   const resolvedSkillSources = (() => {
     try {
       return resolveSkillSourcesSelection({
@@ -527,8 +520,8 @@ async function main(): Promise<void> {
     }
   })();
   const fromAfFile = resolveImportFlagAlias({
-    importFlagValue: values.import as string | undefined,
-    fromAfFlagValue: values["from-af"] as string | undefined,
+    importFlagValue: values.import,
+    fromAfFlagValue: values["from-af"],
   });
   const isHeadless = values.prompt || values.run || !process.stdin.isTTY;
 
@@ -865,23 +858,23 @@ async function main(): Promise<void> {
   // Set tool filter if provided (controls which tools are loaded)
   if (values.tools !== undefined) {
     const { toolFilter } = await import("./tools/filter");
-    toolFilter.setEnabledTools(values.tools as string);
+    toolFilter.setEnabledTools(values.tools);
   }
 
   // Set CLI permission overrides if provided
   if (values.allowedTools || values.disallowedTools) {
     const { cliPermissions } = await import("./permissions/cli");
     if (values.allowedTools) {
-      cliPermissions.setAllowedTools(values.allowedTools as string);
+      cliPermissions.setAllowedTools(values.allowedTools);
     }
     if (values.disallowedTools) {
-      cliPermissions.setDisallowedTools(values.disallowedTools as string);
+      cliPermissions.setDisallowedTools(values.disallowedTools);
     }
   }
 
   // Set permission mode if provided (or via --yolo alias)
-  const permissionModeValue = values["permission-mode"] as string | undefined;
-  const yoloMode = values.yolo as boolean | undefined;
+  const permissionModeValue = values["permission-mode"];
+  const yoloMode = values.yolo;
 
   if (yoloMode || permissionModeValue) {
     if (yoloMode) {
diff --git a/src/tests/cli/args.test.ts b/src/tests/cli/args.test.ts
index 227d4ae..933e6d0 100644
--- a/src/tests/cli/args.test.ts
+++ b/src/tests/cli/args.test.ts
@@ -16,7 +16,14 @@ describe("shared CLI arg schema", () => {
     const validModes = new Set(["interactive", "headless", "both"]);
     const validTypes = new Set(["boolean", "string"]);
 
-    for (const [flagName, definition] of Object.entries(CLI_FLAG_CATALOG)) {
+    for (const [flagName, definition] of Object.entries(
+      CLI_FLAG_CATALOG,
+    ) as Array<
+      [
+        keyof typeof CLI_FLAG_CATALOG,
+        (typeof CLI_FLAG_CATALOG)[keyof typeof CLI_FLAG_CATALOG],
+      ]
+    >) {
       expect(validModes.has(definition.mode)).toBe(true);
       expect(validTypes.has(definition.parser.type)).toBe(true);
       expect(CLI_OPTIONS[flagName]).toEqual(definition.parser);