diff --git a/src/plugin/hooks/create-model-fallback-session-hook.ts b/src/plugin/hooks/create-model-fallback-session-hook.ts
new file mode 100644
index 000000000..96bac6d13
--- /dev/null
+++ b/src/plugin/hooks/create-model-fallback-session-hook.ts
@@ -0,0 +1,131 @@
+import type { OhMyOpenCodeConfig, HookName } from "../../config"
+
+import { createModelFallbackHook } from "../../hooks"
+import { normalizeSDKResponse } from "../../shared"
+
+import { resolveModelFallbackEnabled } from "./model-fallback-config"
+
+type SafeHook = <THook>(hookName: HookName, factory: () => THook) => THook | null
+
+type ModelFallbackSessionContext = {
+  directory: string
+  client: {
+    session: {
+      get: (input: { path: { id: string } }) => Promise<unknown>
+      update: (input: {
+        path: { id: string }
+        body: { title: string }
+        query: { directory: string }
+      }) => Promise<unknown>
+    }
+    tui: {
+      showToast: (input: {
+        body: {
+          title: string
+          message: string
+          variant: "success" | "error" | "info" | "warning"
+          duration: number
+        }
+      }) => Promise<unknown>
+    }
+  }
+}
+
+function createFallbackTitleUpdater(
+  ctx: ModelFallbackSessionContext,
+  enabled: boolean,
+):
+  | ((input: {
+      sessionID: string
+      providerID: string
+      modelID: string
+      variant?: string
+    }) => Promise<void>)
+  | undefined {
+  if (!enabled) {
+    return undefined
+  }
+
+  const fallbackTitleMaxEntries = 200
+  const fallbackTitleState = new Map<string, { baseTitle?: string; lastKey?: string }>()
+
+  return async (input) => {
+    const key = `${input.providerID}/${input.modelID}${input.variant ? `:${input.variant}` : ""}`
+    const existing = fallbackTitleState.get(input.sessionID) ?? {}
+    if (existing.lastKey === key) {
+      return
+    }
+
+    if (!existing.baseTitle) {
+      const sessionResp = await ctx.client.session.get({ path: { id: input.sessionID } }).catch(() => null)
+      const sessionInfo = sessionResp
+        ? normalizeSDKResponse(sessionResp, null as { title?: string } | null, {
+            preferResponseOnMissingData: true,
+          })
+        : null
+      const rawTitle = sessionInfo?.title
+      if (typeof rawTitle === "string" && rawTitle.length > 0) {
+        existing.baseTitle = rawTitle.replace(/\s*\[fallback:[^\]]+\]$/i, "").trim()
+      } else {
+        existing.baseTitle = "Session"
+      }
+    }
+
+    const variantLabel = input.variant ? ` ${input.variant}` : ""
+    const newTitle = `${existing.baseTitle} [fallback: ${input.providerID}/${input.modelID}${variantLabel}]`
+
+    await ctx.client.session
+      .update({
+        path: { id: input.sessionID },
+        body: { title: newTitle },
+        query: { directory: ctx.directory },
+      })
+      .catch(() => {})
+
+    existing.lastKey = key
+    fallbackTitleState.set(input.sessionID, existing)
+    if (fallbackTitleState.size > fallbackTitleMaxEntries) {
+      const oldestKey = fallbackTitleState.keys().next().value
+      if (oldestKey) {
+        fallbackTitleState.delete(oldestKey)
+      }
+    }
+  }
+}
+
+export function createConfiguredModelFallbackHook(args: {
+  ctx: ModelFallbackSessionContext
+  pluginConfig: OhMyOpenCodeConfig
+  isHookEnabled: (hookName: HookName) => boolean
+  safeHook: SafeHook
+}): ReturnType<typeof createModelFallbackHook> | null {
+  const { ctx, pluginConfig, isHookEnabled, safeHook } = args
+  const isModelFallbackEnabled = resolveModelFallbackEnabled(pluginConfig)
+
+  if (!isModelFallbackEnabled || !isHookEnabled("model-fallback")) {
+    return null
+  }
+
+  const onApplied = createFallbackTitleUpdater(
+    ctx,
+    pluginConfig.experimental?.model_fallback_title ?? false,
+  )
+
+  return safeHook("model-fallback", () =>
+    createModelFallbackHook({
+      toast: async ({ title, message, variant, duration }) => {
+        await ctx.client.tui
+          .showToast({
+            body: {
+              title,
+              message,
+              variant: variant ?? "warning",
+              duration: duration ?? 5000,
+            },
+          })
+          .catch(() => {})
+      },
+      onApplied,
+    }),
+  )
+}
diff --git a/src/plugin/hooks/create-session-hooks.ts b/src/plugin/hooks/create-session-hooks.ts
index daa5e4ff5..3dcc0d7d6 100644
--- a/src/plugin/hooks/create-session-hooks.ts
+++ b/src/plugin/hooks/create-session-hooks.ts
@@ -1,13 +1,10 @@
 import type { OhMyOpenCodeConfig, HookName } from "../../config"
 import type { ModelCacheState } from "../../plugin-state"
-import type { PluginContext } from "../types"
-
 import {
   createContextWindowMonitorHook,
   createSessionRecoveryHook,
   createSessionNotification,
   createThinkModeHook,
-  createModelFallbackHook,
   createAnthropicContextWindowLimitRecoveryHook,
   createAutoUpdateCheckerHook,
   createAgentUsageReminderHook,
@@ -31,10 +28,10 @@ import {
   detectExternalNotificationPlugin,
   getNotificationConflictWarning,
   log,
-  normalizeSDKResponse,
 } from "../../shared"
 import { safeCreateHook } from "../../shared/safe-create-hook"
 import { sessionExists } from "../../tools"
+import { createConfiguredModelFallbackHook } from "./create-model-fallback-session-hook"
 
 export type SessionHooks = {
   contextWindowMonitor: ReturnType<typeof createContextWindowMonitorHook> | null
@@ -42,7 +39,7 @@ export type SessionHooks = {
   sessionRecovery: ReturnType<typeof createSessionRecoveryHook> | null
   sessionNotification: ReturnType<typeof createSessionNotification> | null
   thinkMode: ReturnType<typeof createThinkModeHook> | null
-  modelFallback: ReturnType<typeof createModelFallbackHook> | null
+  modelFallback: ReturnType<typeof createConfiguredModelFallbackHook>
   anthropicContextWindowLimitRecovery: ReturnType<typeof createAnthropicContextWindowLimitRecoveryHook> | null
   autoUpdateChecker: ReturnType<typeof createAutoUpdateCheckerHook> | null
   agentUsageReminder: ReturnType<typeof createAgentUsageReminderHook> | null
@@ -63,7 +60,7 @@ export type SessionHooks = {
 }
 
 export function createSessionHooks(args: {
-  ctx: PluginContext
+  ctx: Parameters<typeof createContextWindowMonitorHook>[0]
   pluginConfig: OhMyOpenCodeConfig
   modelCacheState: ModelCacheState
   isHookEnabled: (hookName: HookName) => boolean
@@ -105,73 +102,12 @@ export function createSessionHooks(args: {
     ? safeHook("think-mode", () => createThinkModeHook())
     : null
 
-  const enableFallbackTitle = pluginConfig.experimental?.model_fallback_title ?? false
-  const fallbackTitleMaxEntries = 200
-  const fallbackTitleState = new Map<string, { baseTitle?: string; lastKey?: string }>()
-  const updateFallbackTitle = async (input: {
-    sessionID: string
-    providerID: string
-    modelID: string
-    variant?: string
-  }) => {
-    if (!enableFallbackTitle) return
-    const key = `${input.providerID}/${input.modelID}${input.variant ? `:${input.variant}` : ""}`
-    const existing = fallbackTitleState.get(input.sessionID) ?? {}
-    if (existing.lastKey === key) return
-
-    if (!existing.baseTitle) {
-      const sessionResp = await ctx.client.session.get({ path: { id: input.sessionID } }).catch(() => null)
-      const sessionInfo = sessionResp
-        ? normalizeSDKResponse(sessionResp, null as { title?: string } | null, { preferResponseOnMissingData: true })
-        : null
-      const rawTitle = sessionInfo?.title
-      if (typeof rawTitle === "string" && rawTitle.length > 0) {
-        existing.baseTitle = rawTitle.replace(/\s*\[fallback:[^\]]+\]$/i, "").trim()
-      } else {
-        existing.baseTitle = "Session"
-      }
-    }
-
-    const variantLabel = input.variant ? ` ${input.variant}` : ""
-    const newTitle = `${existing.baseTitle} [fallback: ${input.providerID}/${input.modelID}${variantLabel}]`
-
-    await ctx.client.session
-      .update({
-        path: { id: input.sessionID },
-        body: { title: newTitle },
-        query: { directory: ctx.directory },
-      })
-      .catch(() => {})
-
-    existing.lastKey = key
-    fallbackTitleState.set(input.sessionID, existing)
-    if (fallbackTitleState.size > fallbackTitleMaxEntries) {
-      const oldestKey = fallbackTitleState.keys().next().value
-      if (oldestKey) fallbackTitleState.delete(oldestKey)
-    }
-  }
-
-  // Model fallback hook (configurable via model_fallback config + disabled_hooks)
-  // This handles automatic model switching when model errors occur
-  const isModelFallbackConfigEnabled = pluginConfig.model_fallback ?? false
-  const modelFallback = isModelFallbackConfigEnabled && isHookEnabled("model-fallback")
-    ? safeHook("model-fallback", () =>
-      createModelFallbackHook({
-        toast: async ({ title, message, variant, duration }) => {
-          await ctx.client.tui
-            .showToast({
-              body: {
-                title,
-                message,
-                variant: variant ?? "warning",
-                duration: duration ?? 5000,
-              },
-            })
-            .catch(() => {})
-        },
-        onApplied: enableFallbackTitle ? updateFallbackTitle : undefined,
-      }))
-    : null
+  const modelFallback = createConfiguredModelFallbackHook({
+    ctx,
+    pluginConfig,
+    isHookEnabled,
+    safeHook,
+  })
 
   const anthropicContextWindowLimitRecovery = isHookEnabled("anthropic-context-window-limit-recovery")
     ? safeHook("anthropic-context-window-limit-recovery", () =>
diff --git a/src/plugin/hooks/model-fallback-config.test.ts b/src/plugin/hooks/model-fallback-config.test.ts
new file mode 100644
index 000000000..283b7946b
--- /dev/null
+++ b/src/plugin/hooks/model-fallback-config.test.ts
@@ -0,0 +1,63 @@
+declare const require: (name: string) => any
+const { describe, expect, test } = require("bun:test")
+
+import type { OhMyOpenCodeConfig } from "../../config"
+
+import {
+  hasConfiguredModelFallbacks,
+  resolveModelFallbackEnabled,
+} from "./model-fallback-config"
+
+describe("model-fallback-config", () => {
+  test("detects agent fallback_models configuration", () => {
+    //#given
+    const pluginConfig: OhMyOpenCodeConfig = {
+      agents: {
+        sisyphus: {
+          fallback_models: ["openai/gpt-5.2", "anthropic/claude-opus-4-6"],
+        },
+      },
+    }
+
+    //#when
+    const result = hasConfiguredModelFallbacks(pluginConfig)
+
+    //#then
+    expect(result).toBe(true)
+  })
+
+  test("auto-enables model fallback when category fallback_models are configured", () => {
+    //#given
+    const pluginConfig: OhMyOpenCodeConfig = {
+      categories: {
+        quick: {
+          fallback_models: ["openai/gpt-5.2"],
+        },
+      },
+    }
+
+    //#when
+    const result = resolveModelFallbackEnabled(pluginConfig)
+
+    //#then
+    expect(result).toBe(true)
+  })
+
+  test("keeps model fallback disabled when explicitly turned off", () => {
+    //#given
+    const pluginConfig: OhMyOpenCodeConfig = {
+      model_fallback: false,
+      agents: {
+        sisyphus: {
+          fallback_models: ["openai/gpt-5.2"],
+        },
+      },
+    }
+
+    //#when
+    const result = resolveModelFallbackEnabled(pluginConfig)
+
+    //#then
+    expect(result).toBe(false)
+  })
+})
diff --git a/src/plugin/hooks/model-fallback-config.ts b/src/plugin/hooks/model-fallback-config.ts
new file mode 100644
index 000000000..a63b3ae58
--- /dev/null
+++ b/src/plugin/hooks/model-fallback-config.ts
@@ -0,0 +1,33 @@
+import type { OhMyOpenCodeConfig } from "../../config"
+
+import { log, normalizeFallbackModels } from "../../shared"
+
+type FallbackModelsConfig = {
+  fallback_models?: string | string[]
+}
+
+function hasFallbackModels(config: FallbackModelsConfig | undefined): boolean {
+  return (normalizeFallbackModels(config?.fallback_models)?.length ?? 0) > 0
+}
+
+export function hasConfiguredModelFallbacks(pluginConfig: OhMyOpenCodeConfig): boolean {
+  const agentConfigs = Object.values<FallbackModelsConfig | undefined>(pluginConfig.agents ?? {})
+  if (agentConfigs.some(hasFallbackModels)) {
+    return true
+  }
+
+  const categoryConfigs = Object.values<FallbackModelsConfig | undefined>(pluginConfig.categories ?? {})
+  return categoryConfigs.some(hasFallbackModels)
+}
+
+export function resolveModelFallbackEnabled(pluginConfig: OhMyOpenCodeConfig): boolean {
+  const hasConfiguredFallbacks = hasConfiguredModelFallbacks(pluginConfig)
+
+  if (pluginConfig.model_fallback === false && hasConfiguredFallbacks) {
+    log(
+      "model_fallback is disabled while fallback_models are configured; set model_fallback=true to keep provider fallback retries enabled",
+    )
+  }
+
+  return pluginConfig.model_fallback ?? hasConfiguredFallbacks
+}
diff --git a/src/shared/model-error-classifier.test.ts b/src/shared/model-error-classifier.test.ts
index d359c26d3..a9fa2fb99 100644
--- a/src/shared/model-error-classifier.test.ts
+++ b/src/shared/model-error-classifier.test.ts
@@ -40,6 +40,28 @@ describe("model-error-classifier", () => {
     expect(result).toBe(true)
   })
 
+  test("treats FreeUsageLimitError names as retryable", () => {
+    //#given
+    const error = { name: "FreeUsageLimitError" }
+
+    //#when
+    const result = shouldRetryError(error)
+
+    //#then
+    expect(result).toBe(true)
+  })
+
+  test("treats free tier usage limit messages as retryable", () => {
+    //#given
+    const error = { message: "Free tier daily limit reached for this provider" }
+
+    //#when
+    const result = shouldRetryError(error)
+
+    //#then
+    expect(result).toBe(true)
+  })
+
   test("selectFallbackProvider prefers first connected provider in preference order", () => {
     //#given
     readConnectedProvidersCacheMock.mockReturnValue(["anthropic", "nvidia"])
diff --git a/src/shared/model-error-classifier.ts b/src/shared/model-error-classifier.ts
index 22d5606c7..ecfd8f036 100644
--- a/src/shared/model-error-classifier.ts
+++ b/src/shared/model-error-classifier.ts
@@ -6,13 +6,14 @@ import { readConnectedProvidersCache } from "./connected-providers-cache"
  * These errors completely halt the action loop and should trigger fallback retry.
  */
 const RETRYABLE_ERROR_NAMES = new Set([
-  "ProviderModelNotFoundError",
-  "RateLimitError",
-  "QuotaExceededError",
-  "InsufficientCreditsError",
-  "ModelUnavailableError",
-  "ProviderConnectionError",
-  "AuthenticationError",
+  "providermodelnotfounderror",
+  "ratelimiterror",
+  "quotaexceedederror",
+  "insufficientcreditserror",
+  "modelunavailableerror",
+  "providerconnectionerror",
+  "authenticationerror",
+  "freeusagelimiterror",
 ])
 
 /**
@@ -20,24 +21,28 @@ const RETRYABLE_ERROR_NAMES = new Set([
  * These errors are typically user-induced or fixable without switching models.
  */
 const NON_RETRYABLE_ERROR_NAMES = new Set([
-  "MessageAbortedError",
-  "PermissionDeniedError",
-  "ContextLengthError",
-  "TimeoutError",
-  "ValidationError",
-  "SyntaxError",
-  "UserError",
+  "messageabortederror",
+  "permissiondeniederror",
+  "contextlengtherror",
+  "timeouterror",
+  "validationerror",
+  "syntaxerror",
+  "usererror",
 ])
 
 /**
  * Message patterns that indicate a retryable error even without a known error name.
  */
-const RETRYABLE_MESSAGE_PATTERNS = [
+const RETRYABLE_MESSAGE_PATTERNS: Array<string | RegExp> = [
   "rate_limit",
   "rate limit",
   "quota",
   "quota will reset after",
   "usage limit has been reached",
+  /free\s+usage/i,
+  /free\s+tier/i,
+  /daily\s+limit/i,
+  /limit\s+reached/i,
   "all credentials for model",
   "cooling down",
   "exhausted your capacity",
@@ -77,6 +82,11 @@ function hasProviderAutoRetrySignal(message: string): boolean {
   return AUTO_RETRY_GATE_PATTERNS.some((pattern) => message.includes(pattern))
 }
 
+function matchesRetryableMessagePattern(message: string): boolean {
+  return RETRYABLE_MESSAGE_PATTERNS.some((pattern) =>
+    typeof pattern === "string" ? message.includes(pattern) : pattern.test(message))
+}
+
 export interface ErrorInfo {
   name?: string
   message?: string
@@ -89,12 +99,14 @@ export interface ErrorInfo {
 export function isRetryableModelError(error: ErrorInfo): boolean {
   // If we have an error name, check against known lists
   if (error.name) {
+    const normalizedErrorName = error.name.toLowerCase()
+
     // Explicit non-retryable takes precedence
-    if (NON_RETRYABLE_ERROR_NAMES.has(error.name)) {
+    if (NON_RETRYABLE_ERROR_NAMES.has(normalizedErrorName)) {
       return false
     }
     // Check if it's a known retryable error
-    if (RETRYABLE_ERROR_NAMES.has(error.name)) {
+    if (RETRYABLE_ERROR_NAMES.has(normalizedErrorName)) {
       return true
     }
   }
@@ -104,7 +116,7 @@ export function isRetryableModelError(error: ErrorInfo): boolean {
   if (hasProviderAutoRetrySignal(msg)) {
     return true
   }
-  return RETRYABLE_MESSAGE_PATTERNS.some((pattern) => msg.includes(pattern))
+  return matchesRetryableMessagePattern(msg)
 }
 
 /**