diff --git a/server/storage/models/.gitignore b/server/storage/models/.gitignore
index f5c78ac877..5e83df7bcc 100644
--- a/server/storage/models/.gitignore
+++ b/server/storage/models/.gitignore
@@ -9,3 +9,4 @@ gemini
 togetherAi
 tesseract
 ppio
+context-windows/*
\ No newline at end of file
diff --git a/server/utils/AiProviders/anthropic/index.js b/server/utils/AiProviders/anthropic/index.js
index c4f53acf63..450b376b3e 100644
--- a/server/utils/AiProviders/anthropic/index.js
+++ b/server/utils/AiProviders/anthropic/index.js
@@ -45,11 +45,11 @@ class AnthropicLLM {
   }
 
   static promptWindowLimit(modelName) {
-    return MODEL_MAP.anthropic[modelName] ?? 100_000;
+    return MODEL_MAP.get("anthropic", modelName) ?? 100_000;
   }
 
   promptWindowLimit() {
-    return MODEL_MAP.anthropic[this.model] ?? 100_000;
+    return MODEL_MAP.get("anthropic", this.model) ?? 100_000;
   }
 
   isValidChatCompletionModel(_modelName = "") {
diff --git a/server/utils/AiProviders/cohere/index.js b/server/utils/AiProviders/cohere/index.js
index 33b65df21c..a6647f5b65 100644
--- a/server/utils/AiProviders/cohere/index.js
+++ b/server/utils/AiProviders/cohere/index.js
@@ -63,11 +63,11 @@ class CohereLLM {
   }
 
   static promptWindowLimit(modelName) {
-    return MODEL_MAP.cohere[modelName] ?? 4_096;
+    return MODEL_MAP.get("cohere", modelName) ?? 4_096;
   }
 
   promptWindowLimit() {
-    return MODEL_MAP.cohere[this.model] ?? 4_096;
+    return MODEL_MAP.get("cohere", this.model) ?? 4_096;
   }
 
   async isValidChatCompletionModel(model = "") {
diff --git a/server/utils/AiProviders/deepseek/index.js b/server/utils/AiProviders/deepseek/index.js
index b91332a84a..4b5b334bfe 100644
--- a/server/utils/AiProviders/deepseek/index.js
+++ b/server/utils/AiProviders/deepseek/index.js
@@ -29,7 +29,9 @@ class DeepSeekLLM {
 
     this.embedder = embedder ?? new NativeEmbedder();
     this.defaultTemp = 0.7;
-    this.log("Initialized with model:", this.model);
+    this.log(
+      `Initialized ${this.model} with context window ${this.promptWindowLimit()}`
+    );
   }
 
   log(text, ...args) {
@@ -53,11 +55,11 @@ class DeepSeekLLM {
   }
 
   static promptWindowLimit(modelName) {
-    return MODEL_MAP.deepseek[modelName] ?? 8192;
+    return MODEL_MAP.get("deepseek", modelName) ?? 8192;
   }
 
   promptWindowLimit() {
-    return MODEL_MAP.deepseek[this.model] ?? 8192;
+    return MODEL_MAP.get("deepseek", this.model) ?? 8192;
   }
 
   async isValidChatCompletionModel(modelName = "") {
diff --git a/server/utils/AiProviders/gemini/defaultModels.js b/server/utils/AiProviders/gemini/defaultModels.js
index fde63341d2..4a52dc99c6 100644
--- a/server/utils/AiProviders/gemini/defaultModels.js
+++ b/server/utils/AiProviders/gemini/defaultModels.js
@@ -1,7 +1,7 @@
 const { MODEL_MAP } = require("../modelMap");
 
 const stableModels = [
-  // %STABLE_MODELS% - updated 2025-04-07T20:29:49.276Z
+  // %STABLE_MODELS% - updated 2025-05-13T23:13:58.920Z
   "gemini-1.5-pro-001",
   "gemini-1.5-pro-002",
   "gemini-1.5-pro",
@@ -14,6 +14,7 @@ const stableModels = [
   "gemini-2.0-flash-001",
   "gemini-2.0-flash-lite-001",
   "gemini-2.0-flash-lite",
+  "gemini-2.0-flash-preview-image-generation",
   // %EOC_STABLE_MODELS%
 ];
 
@@ -22,7 +23,7 @@ const stableModels = [
 // generally, v1beta models have `exp` in the name, but not always
 // so we check for both against a static list as well via API.
 const v1BetaModels = [
-  // %V1BETA_MODELS% - updated 2025-04-07T20:29:49.276Z
+  // %V1BETA_MODELS% - updated 2025-05-13T23:13:58.920Z
   "gemini-1.5-pro-latest",
   "gemini-1.5-flash-latest",
   "gemini-1.5-flash-8b-latest",
@@ -30,6 +31,9 @@ const v1BetaModels = [
   "gemini-1.5-flash-8b-exp-0924",
   "gemini-2.5-pro-exp-03-25",
   "gemini-2.5-pro-preview-03-25",
+  "gemini-2.5-flash-preview-04-17",
+  "gemini-2.5-flash-preview-04-17-thinking",
+  "gemini-2.5-pro-preview-05-06",
   "gemini-2.0-flash-exp",
   "gemini-2.0-flash-exp-image-generation",
   "gemini-2.0-flash-lite-preview-02-05",
@@ -41,6 +45,7 @@ const v1BetaModels = [
   "gemini-2.0-flash-thinking-exp",
   "gemini-2.0-flash-thinking-exp-1219",
   "learnlm-1.5-pro-experimental",
+  "learnlm-2.0-flash-experimental",
   "gemma-3-1b-it",
   "gemma-3-4b-it",
   "gemma-3-12b-it",
@@ -48,17 +53,17 @@ const v1BetaModels = [
   // %EOC_V1BETA_MODELS%
 ];
 
-const defaultGeminiModels = [
+const defaultGeminiModels = () => [
   ...stableModels.map((model) => ({
     id: model,
     name: model,
-    contextWindow: MODEL_MAP.gemini[model],
+    contextWindow: MODEL_MAP.get("gemini", model),
     experimental: false,
   })),
   ...v1BetaModels.map((model) => ({
     id: model,
     name: model,
-    contextWindow: MODEL_MAP.gemini[model],
+    contextWindow: MODEL_MAP.get("gemini", model),
     experimental: true,
   })),
 ];
diff --git a/server/utils/AiProviders/gemini/index.js b/server/utils/AiProviders/gemini/index.js
index bd2268e517..c7d39bc782 100644
--- a/server/utils/AiProviders/gemini/index.js
+++ b/server/utils/AiProviders/gemini/index.js
@@ -107,7 +107,7 @@ class GeminiLLM {
     try {
       const cacheModelPath = path.resolve(cacheFolder, "models.json");
       if (!fs.existsSync(cacheModelPath))
-        return MODEL_MAP.gemini[modelName] ?? 30_720;
+        return MODEL_MAP.get("gemini", modelName) ?? 30_720;
 
       const models = safeJsonParse(fs.readFileSync(cacheModelPath));
       const model = models.find((model) => model.id === modelName);
@@ -118,15 +118,14 @@ class GeminiLLM {
       return model.contextWindow;
     } catch (e) {
       console.error(`GeminiLLM:promptWindowLimit`, e.message);
-      return MODEL_MAP.gemini[modelName] ?? 30_720;
+      return MODEL_MAP.get("gemini", modelName) ?? 30_720;
     }
   }
 
   promptWindowLimit() {
     try {
       if (!fs.existsSync(this.cacheModelPath))
-        return MODEL_MAP.gemini[this.model] ?? 30_720;
-
+        return MODEL_MAP.get("gemini", this.model) ?? 30_720;
       const models = safeJsonParse(fs.readFileSync(this.cacheModelPath));
       const model = models.find((model) => model.id === this.model);
       if (!model)
@@ -136,7 +135,7 @@ class GeminiLLM {
       return model.contextWindow;
     } catch (e) {
       console.error(`GeminiLLM:promptWindowLimit`, e.message);
-      return MODEL_MAP.gemini[this.model] ?? 30_720;
+      return MODEL_MAP.get("gemini", this.model) ?? 30_720;
     }
   }
 
@@ -281,7 +280,7 @@ class GeminiLLM {
 
     if (allModels.length === 0) {
       console.error(`Gemini:getGeminiModels - No models found`);
-      return defaultGeminiModels;
+      return defaultGeminiModels();
     }
 
     console.log(
diff --git a/server/utils/AiProviders/gemini/syncStaticLists.mjs b/server/utils/AiProviders/gemini/syncStaticLists.mjs
index 42382fae38..b276995acd 100644
--- a/server/utils/AiProviders/gemini/syncStaticLists.mjs
+++ b/server/utils/AiProviders/gemini/syncStaticLists.mjs
@@ -9,7 +9,6 @@
 import fs from "fs";
 import path from "path";
 import dotenv from "dotenv";
-import { MODEL_MAP } from "../modelMap.js";
 
 dotenv.config({ path: `../../../.env.development` });
 const existingCachePath = path.resolve('../../../storage/models/gemini')
@@ -46,34 +45,4 @@ function updateDefaultModelsFile(models) {
   fs.writeFileSync(path.join("./defaultModels.js"), defaultModelFileContents);
   console.log("Updated defaultModels.js. Dont forget to `yarn lint` and commit!");
 }
-
-function updateModelMap(models) {
-  const existingModelMap = MODEL_MAP;
-  console.log('Updating modelMap.js `gemini` object...')
-  console.log(`Removed existing gemini object (${Object.keys(existingModelMap.gemini).length} models) from modelMap.js`);
-  existingModelMap.gemini = {};
-
-  for (const model of models) existingModelMap.gemini[model.id] = model.contextWindow;
-  console.log(`Updated modelMap.js 'gemini' object with ${Object.keys(existingModelMap.gemini).length} models from API`);
-
-  // Update the modelMap.js file
-  const contents = `/**
- * The model name and context window for all know model windows
- * that are available through providers which has discrete model options.
- * This file is automatically generated by syncStaticLists.mjs
- * and should not be edited manually.
- * 
- * Last updated: ${new Date().toISOString()}
- */
-const MODEL_MAP = {
-  ${Object.entries(existingModelMap).map(([key, value]) => `${key}: ${JSON.stringify(value, null, 2)}`).join(',\n')}
-};
-
-module.exports = { MODEL_MAP };
-`;
-  fs.writeFileSync(path.resolve("../modelMap.js"), contents);
-  console.log('Updated modelMap.js `gemini` object. Dont forget to `yarn lint` and commit!');
-}
-
 updateDefaultModelsFile(models);
-updateModelMap(models);
diff --git a/server/utils/AiProviders/groq/index.js b/server/utils/AiProviders/groq/index.js
index 9e7e77fa16..8eddefab0c 100644
--- a/server/utils/AiProviders/groq/index.js
+++ b/server/utils/AiProviders/groq/index.js
@@ -49,11 +49,11 @@ class GroqLLM {
   }
 
   static promptWindowLimit(modelName) {
-    return MODEL_MAP.groq[modelName] ?? 8192;
+    return MODEL_MAP.get("groq", modelName) ?? 8192;
   }
 
   promptWindowLimit() {
-    return MODEL_MAP.groq[this.model] ?? 8192;
+    return MODEL_MAP.get("groq", this.model) ?? 8192;
   }
 
   async isValidChatCompletionModel(modelName = "") {
diff --git a/server/utils/AiProviders/modelMap/index.js b/server/utils/AiProviders/modelMap/index.js
new file mode 100644
index 0000000000..dbf0aff6a6
--- /dev/null
+++ b/server/utils/AiProviders/modelMap/index.js
@@ -0,0 +1,140 @@
+const path = require("path");
+const fs = require("fs");
+const LEGACY_MODEL_MAP = require("./legacy");
+
+class ContextWindowFinder {
+  static instance = null;
+  static modelMap = LEGACY_MODEL_MAP;
+
+  /**
+   * Mapping for AnythingLLM provider <> LiteLLM provider
+   * @type {Record<string, string>}
+   */
+  static trackedProviders = {
+    anthropic: "anthropic",
+    openai: "openai",
+    cohere: "cohere_chat",
+    gemini: "vertex_ai-language-models",
+    groq: "groq",
+    xai: "xai",
+    deepseek: "deepseek",
+  };
+  static expiryMs = 1000 * 60 * 60 * 24 * 3; // 3 days
+  static remoteUrl =
+    "https://raw.githubusercontent.com/BerriAI/litellm/main/model_prices_and_context_window.json";
+
+  cacheLocation = path.resolve(
+    process.env.STORAGE_DIR
+      ? path.resolve(process.env.STORAGE_DIR, "models", "context-windows")
+      : path.resolve(__dirname, `../../../storage/models/context-windows`)
+  );
+  cacheFilePath = path.resolve(this.cacheLocation, "context-windows.json");
+  cacheFileExpiryPath = path.resolve(this.cacheLocation, ".cached_at");
+
+  constructor() {
+    if (ContextWindowFinder.instance) return ContextWindowFinder.instance;
+    ContextWindowFinder.instance = this;
+    if (!fs.existsSync(this.cacheLocation))
+      fs.mkdirSync(this.cacheLocation, { recursive: true });
+    this.#pullRemoteModelMap();
+  }
+
+  log(text, ...args) {
+    console.log(`\x1b[33m[ContextWindowFinder]\x1b[0m ${text}`, ...args);
+  }
+
+  /**
+   * Checks if the cache is stale by checking if the cache file exists and if the cache file is older than the expiry time.
+   * @returns {boolean}
+   */
+  get isCacheStale() {
+    if (!fs.existsSync(this.cacheFileExpiryPath)) return true;
+    const cachedAt = fs.readFileSync(this.cacheFileExpiryPath, "utf8");
+    return Date.now() - cachedAt > ContextWindowFinder.expiryMs;
+  }
+
+  get cache() {
+    if (!fs.existsSync(this.cacheFileExpiryPath)) return null;
+    if (!this.isCacheStale)
+      return JSON.parse(
+        fs.readFileSync(this.cacheFilePath, { encoding: "utf8" })
+      );
+    return null;
+  }
+
+  /**
+   * Pulls the remote model map from the remote URL, formats it and caches it.
+   * @returns {Record<string, Record<string, number>>} - The formatted model map
+   */
+  async #pullRemoteModelMap() {
+    const remoteContexWindowMap = await fetch(ContextWindowFinder.remoteUrl)
+      .then((res) => res.json())
+      .then((data) => {
+        fs.writeFileSync(this.cacheFilePath, JSON.stringify(data, null, 2));
+        fs.writeFileSync(this.cacheFileExpiryPath, Date.now().toString());
+        this.log("Remote model map synced and cached");
+        return data;
+      })
+      .catch((error) => {
+        this.log("Error syncing remote model map", error);
+        return null;
+      });
+    if (!remoteContexWindowMap) return null;
+
+    const modelMap = this.#formatModelMap(remoteContexWindowMap);
+    fs.writeFileSync(this.cacheFilePath, JSON.stringify(modelMap, null, 2));
+    fs.writeFileSync(this.cacheFileExpiryPath, Date.now().toString());
+    return modelMap;
+  }
+
+  /**
+   * Formats the remote model map to a format that is compatible with how we store the model map
+   * for all providers who use it.
+   * @param {Record<string, any>} modelMap - The remote model map
+   * @returns {Record<string, Record<string, number>>} - The formatted model map
+   */
+  #formatModelMap(modelMap = {}) {
+    const formattedModelMap = {};
+
+    for (const [provider, liteLLMProviderTag] of Object.entries(
+      ContextWindowFinder.trackedProviders
+    )) {
+      formattedModelMap[provider] = {};
+      const matches = Object.entries(modelMap).filter(
+        ([_key, config]) => config.litellm_provider === liteLLMProviderTag
+      );
+      for (const [key, config] of matches) {
+        const contextWindow = Number(config.max_input_tokens);
+        if (isNaN(contextWindow)) continue;
+
+        // Some models have a provider/model-tag format, so we need to get the last part since we dont do paths
+        // for names with the exception of some router-providers like OpenRouter or Together.
+        const modelName = key.split("/").pop();
+        formattedModelMap[provider][modelName] = contextWindow;
+      }
+    }
+    return formattedModelMap;
+  }
+
+  /**
+   * Gets the context window for a given provider and model.
+   * @param {string} provider - The provider to get the context window for
+   * @param {string} model - The model to get the context window for
+   * @returns {number} - The context window for the given provider and model
+   */
+  get(provider = null, model = null) {
+    if (!provider || !this.cache || !this.cache[provider]) return null;
+    if (!model) return this.cache[provider];
+    const modelContextWindow = this.cache[provider][model];
+    if (!modelContextWindow) {
+      this.log("Invalid access to model context window - not found in cache", {
+        provider,
+        model,
+      });
+      return null;
+    }
+    return Number(modelContextWindow);
+  }
+}
+
+module.exports = { MODEL_MAP: new ContextWindowFinder() };
diff --git a/server/utils/AiProviders/modelMap.js b/server/utils/AiProviders/modelMap/legacy.js
similarity index 90%
rename from server/utils/AiProviders/modelMap.js
rename to server/utils/AiProviders/modelMap/legacy.js
index a80400c30b..2faf99dc23 100644
--- a/server/utils/AiProviders/modelMap.js
+++ b/server/utils/AiProviders/modelMap/legacy.js
@@ -1,12 +1,4 @@
-/**
- * The model name and context window for all know model windows
- * that are available through providers which has discrete model options.
- * This file is automatically generated by syncStaticLists.mjs
- * and should not be edited manually.
- *
- * Last updated: 2025-04-07T20:29:49.277Z
- */
-const MODEL_MAP = {
+const LEGACY_MODEL_MAP = {
   anthropic: {
     "claude-instant-1.2": 100000,
     "claude-2.0": 100000,
@@ -117,5 +109,4 @@ const MODEL_MAP = {
     "grok-beta": 131072,
   },
 };
-
-module.exports = { MODEL_MAP };
+module.exports = LEGACY_MODEL_MAP;
diff --git a/server/utils/AiProviders/openAi/index.js b/server/utils/AiProviders/openAi/index.js
index 2e5996c939..ee33a12bac 100644
--- a/server/utils/AiProviders/openAi/index.js
+++ b/server/utils/AiProviders/openAi/index.js
@@ -25,6 +25,13 @@ class OpenAiLLM {
 
     this.embedder = embedder ?? new NativeEmbedder();
     this.defaultTemp = 0.7;
+    this.log(
+      `Initialized ${this.model} with context window ${this.promptWindowLimit()}`
+    );
+  }
+
+  log(text, ...args) {
+    console.log(`\x1b[36m[${this.constructor.name}]\x1b[0m ${text}`, ...args);
   }
 
   /**
@@ -54,11 +61,11 @@ class OpenAiLLM {
   }
 
   static promptWindowLimit(modelName) {
-    return MODEL_MAP.openai[modelName] ?? 4_096;
+    return MODEL_MAP.get("openai", modelName) ?? 4_096;
   }
 
   promptWindowLimit() {
-    return MODEL_MAP.openai[this.model] ?? 4_096;
+    return MODEL_MAP.get("openai", this.model) ?? 4_096;
   }
 
   // Short circuit if name has 'gpt' since we now fetch models from OpenAI API
diff --git a/server/utils/AiProviders/xai/index.js b/server/utils/AiProviders/xai/index.js
index 2319e72206..f911627094 100644
--- a/server/utils/AiProviders/xai/index.js
+++ b/server/utils/AiProviders/xai/index.js
@@ -28,7 +28,9 @@ class XAiLLM {
 
     this.embedder = embedder ?? new NativeEmbedder();
     this.defaultTemp = 0.7;
-    this.log("Initialized with model:", this.model);
+    this.log(
+      `Initialized ${this.model} with context window ${this.promptWindowLimit()}`
+    );
   }
 
   log(text, ...args) {
@@ -52,11 +54,11 @@ class XAiLLM {
   }
 
   static promptWindowLimit(modelName) {
-    return MODEL_MAP.xai[modelName] ?? 131_072;
+    return MODEL_MAP.get("xai", modelName) ?? 131_072;
   }
 
   promptWindowLimit() {
-    return MODEL_MAP.xai[this.model] ?? 131_072;
+    return MODEL_MAP.get("xai", this.model) ?? 131_072;
   }
 
   isValidChatCompletionModel(_modelName = "") {