diff --git a/README.md b/README.md
index 0c49608..03f042a 100644
--- a/README.md
+++ b/README.md
@@ -420,6 +420,10 @@ nanobot channels login
 nanobot gateway
 ```
 
+> WhatsApp bridge updates are not applied automatically for existing installations.
+> If you upgrade nanobot and need the latest WhatsApp bridge, run:
+> `rm -rf ~/.nanobot/bridge && nanobot channels login`
+
 </details>
 
 <details>
@@ -671,6 +675,7 @@ Config file: `~/.nanobot/config.json`
 | `custom` | Any OpenAI-compatible endpoint (direct, no LiteLLM) | — |
 | `openrouter` | LLM (recommended, access to all models) | [openrouter.ai](https://openrouter.ai) |
 | `anthropic` | LLM (Claude direct) | [console.anthropic.com](https://console.anthropic.com) |
+| `azure_openai` | LLM (Azure OpenAI) | [portal.azure.com](https://portal.azure.com) |
 | `openai` | LLM (GPT direct) | [platform.openai.com](https://platform.openai.com) |
 | `deepseek` | LLM (DeepSeek direct) | [platform.deepseek.com](https://platform.deepseek.com) |
 | `groq` | LLM + **Voice transcription** (Whisper) | [console.groq.com](https://console.groq.com) |
diff --git a/bridge/src/whatsapp.ts b/bridge/src/whatsapp.ts
index 069d72b..b91bacc 100644
--- a/bridge/src/whatsapp.ts
+++ b/bridge/src/whatsapp.ts
@@ -9,11 +9,17 @@ import makeWASocket, {
   useMultiFileAuthState,
   fetchLatestBaileysVersion,
   makeCacheableSignalKeyStore,
+  downloadMediaMessage,
+  extractMessageContent as baileysExtractMessageContent,
 } from '@whiskeysockets/baileys';
 
 import { Boom } from '@hapi/boom';
 import qrcode from 'qrcode-terminal';
 import pino from 'pino';
+import { writeFile, mkdir } from 'fs/promises';
+import { join } from 'path';
+import { homedir } from 'os';
+import { randomBytes } from 'crypto';
 
 const VERSION = '0.1.0';
 
@@ -24,6 +30,7 @@ export interface InboundMessage {
   content: string;
   timestamp: number;
   isGroup: boolean;
+  media?: string[];
 }
 
 export interface WhatsAppClientOptions {
@@ -110,14 +117,33 @@ export class WhatsAppClient {
       if (type !== 'notify') return;
 
       for (const msg of messages) {
-        // Skip own messages
         if (msg.key.fromMe) continue;
-
-        // Skip status updates
         if (msg.key.remoteJid === 'status@broadcast') continue;
 
-        const content = this.extractMessageContent(msg);
-        if (!content) continue;
+        const unwrapped = baileysExtractMessageContent(msg.message);
+        if (!unwrapped) continue;
+
+        const content = this.getTextContent(unwrapped);
+        let fallbackContent: string | null = null;
+        const mediaPaths: string[] = [];
+
+        if (unwrapped.imageMessage) {
+          fallbackContent = '[Image]';
+          const path = await this.downloadMedia(msg, unwrapped.imageMessage.mimetype ?? undefined);
+          if (path) mediaPaths.push(path);
+        } else if (unwrapped.documentMessage) {
+          fallbackContent = '[Document]';
+          const path = await this.downloadMedia(msg, unwrapped.documentMessage.mimetype ?? undefined,
+            unwrapped.documentMessage.fileName ?? undefined);
+          if (path) mediaPaths.push(path);
+        } else if (unwrapped.videoMessage) {
+          fallbackContent = '[Video]';
+          const path = await this.downloadMedia(msg, unwrapped.videoMessage.mimetype ?? undefined);
+          if (path) mediaPaths.push(path);
+        }
+
+        const finalContent = content || (mediaPaths.length === 0 ? fallbackContent : '') || '';
+        if (!finalContent && mediaPaths.length === 0) continue;
 
         const isGroup = msg.key.remoteJid?.endsWith('@g.us') || false;
 
@@ -125,18 +151,45 @@ export class WhatsAppClient {
           id: msg.key.id || '',
           sender: msg.key.remoteJid || '',
           pn: msg.key.remoteJidAlt || '',
-          content,
+          content: finalContent,
           timestamp: msg.messageTimestamp as number,
           isGroup,
+          ...(mediaPaths.length > 0 ? { media: mediaPaths } : {}),
         });
       }
     });
   }
 
-  private extractMessageContent(msg: any): string | null {
-    const message = msg.message;
-    if (!message) return null;
+  private async downloadMedia(msg: any, mimetype?: string, fileName?: string): Promise<string | null> {
+    try {
+      const mediaDir = join(homedir(), '.nanobot', 'media');
+      await mkdir(mediaDir, { recursive: true });
 
+      const buffer = await downloadMediaMessage(msg, 'buffer', {}) as Buffer;
+
+      let outFilename: string;
+      if (fileName) {
+        // Documents have a filename — use it with a unique prefix to avoid collisions
+        const prefix = `wa_${Date.now()}_${randomBytes(4).toString('hex')}_`;
+        outFilename = prefix + fileName;
+      } else {
+        const mime = mimetype || 'application/octet-stream';
+        // Derive extension from mimetype subtype (e.g. "image/png" → ".png", "application/pdf" → ".pdf")
+        const ext = '.' + (mime.split('/').pop()?.split(';')[0] || 'bin');
+        outFilename = `wa_${Date.now()}_${randomBytes(4).toString('hex')}${ext}`;
+      }
+
+      const filepath = join(mediaDir, outFilename);
+      await writeFile(filepath, buffer);
+
+      return filepath;
+    } catch (err) {
+      console.error('Failed to download media:', err);
+      return null;
+    }
+  }
+
+  private getTextContent(message: any): string | null {
     // Text message
     if (message.conversation) {
       return message.conversation;
@@ -147,19 +200,19 @@ export class WhatsAppClient {
       return message.extendedTextMessage.text;
     }
 
-    // Image with caption
-    if (message.imageMessage?.caption) {
-      return `[Image] ${message.imageMessage.caption}`;
+    // Image with optional caption
+    if (message.imageMessage) {
+      return message.imageMessage.caption || '';
     }
 
-    // Video with caption
-    if (message.videoMessage?.caption) {
-      return `[Video] ${message.videoMessage.caption}`;
+    // Video with optional caption
+    if (message.videoMessage) {
+      return message.videoMessage.caption || '';
     }
 
-    // Document with caption
-    if (message.documentMessage?.caption) {
-      return `[Document] ${message.documentMessage.caption}`;
+    // Document with optional caption
+    if (message.documentMessage) {
+      return message.documentMessage.caption || '';
     }
 
     // Voice/Audio message
diff --git a/nanobot/channels/telegram.py b/nanobot/channels/telegram.py
index 9097496..aaa24e7 100644
--- a/nanobot/channels/telegram.py
+++ b/nanobot/channels/telegram.py
@@ -4,6 +4,8 @@ from __future__ import annotations
 
 import asyncio
 import re
+import time
+import unicodedata
 
 from loguru import logger
 from telegram import BotCommand, ReplyParameters, Update
@@ -19,6 +21,47 @@ from nanobot.utils.helpers import split_message
 TELEGRAM_MAX_MESSAGE_LEN = 4000  # Telegram message character limit
 
 
+def _strip_md(s: str) -> str:
+    """Strip markdown inline formatting from text."""
+    s = re.sub(r'\*\*(.+?)\*\*', r'\1', s)
+    s = re.sub(r'__(.+?)__', r'\1', s)
+    s = re.sub(r'~~(.+?)~~', r'\1', s)
+    s = re.sub(r'`([^`]+)`', r'\1', s)
+    return s.strip()
+
+
+def _render_table_box(table_lines: list[str]) -> str:
+    """Convert markdown pipe-table to compact aligned text for <pre> display."""
+
+    def dw(s: str) -> int:
+        return sum(2 if unicodedata.east_asian_width(c) in ('W', 'F') else 1 for c in s)
+
+    rows: list[list[str]] = []
+    has_sep = False
+    for line in table_lines:
+        cells = [_strip_md(c) for c in line.strip().strip('|').split('|')]
+        if all(re.match(r'^:?-+:?$', c) for c in cells if c):
+            has_sep = True
+            continue
+        rows.append(cells)
+    if not rows or not has_sep:
+        return '\n'.join(table_lines)
+
+    ncols = max(len(r) for r in rows)
+    for r in rows:
+        r.extend([''] * (ncols - len(r)))
+    widths = [max(dw(r[c]) for r in rows) for c in range(ncols)]
+
+    def dr(cells: list[str]) -> str:
+        return '  '.join(f'{c}{" " * (w - dw(c))}' for c, w in zip(cells, widths))
+
+    out = [dr(rows[0])]
+    out.append('  '.join('─' * w for w in widths))
+    for row in rows[1:]:
+        out.append(dr(row))
+    return '\n'.join(out)
+
+
 def _markdown_to_telegram_html(text: str) -> str:
     """
     Convert markdown to Telegram-safe HTML.
@@ -34,6 +77,27 @@ def _markdown_to_telegram_html(text: str) -> str:
 
     text = re.sub(r'```[\w]*\n?([\s\S]*?)```', save_code_block, text)
 
+    # 1.5. Convert markdown tables to box-drawing (reuse code_block placeholders)
+    lines = text.split('\n')
+    rebuilt: list[str] = []
+    li = 0
+    while li < len(lines):
+        if re.match(r'^\s*\|.+\|', lines[li]):
+            tbl: list[str] = []
+            while li < len(lines) and re.match(r'^\s*\|.+\|', lines[li]):
+                tbl.append(lines[li])
+                li += 1
+            box = _render_table_box(tbl)
+            if box != '\n'.join(tbl):
+                code_blocks.append(box)
+                rebuilt.append(f"\x00CB{len(code_blocks) - 1}\x00")
+            else:
+                rebuilt.extend(tbl)
+        else:
+            rebuilt.append(lines[li])
+            li += 1
+    text = '\n'.join(rebuilt)
+
     # 2. Extract and protect inline code
     inline_codes: list[str] = []
     def save_inline_code(m: re.Match) -> str:
@@ -255,42 +319,48 @@ class TelegramChannel(BaseChannel):
         # Send text content
         if msg.content and msg.content != "[empty message]":
             is_progress = msg.metadata.get("_progress", False)
-            draft_id = msg.metadata.get("message_id")
 
             for chunk in split_message(msg.content, TELEGRAM_MAX_MESSAGE_LEN):
-                try:
-                    html = _markdown_to_telegram_html(chunk)
-                    if is_progress and draft_id:
-                        await self._app.bot.send_message_draft(
-                            chat_id=chat_id,
-                            draft_id=draft_id,
-                            text=html,
-                            parse_mode="HTML"
-                        )
-                    else:
-                        await self._app.bot.send_message(
-                            chat_id=chat_id,
-                            text=html,
-                            parse_mode="HTML",
-                            reply_parameters=reply_params
-                        )
-                except Exception as e:
-                    logger.warning("HTML parse failed, falling back to plain text: {}", e)
-                    try:
-                        if is_progress and draft_id:
-                            await self._app.bot.send_message_draft(
-                                chat_id=chat_id,
-                                draft_id=draft_id,
-                                text=chunk
-                            )
-                        else:
-                            await self._app.bot.send_message(
-                                chat_id=chat_id,
-                                text=chunk,
-                                reply_parameters=reply_params
-                            )
-                    except Exception as e2:
-                        logger.error("Error sending Telegram message: {}", e2)
+                # Final response: simulate streaming via draft, then persist
+                if not is_progress:
+                    await self._send_with_streaming(chat_id, chunk, reply_params)
+                else:
+                    await self._send_text(chat_id, chunk, reply_params)
+
+    async def _send_text(self, chat_id: int, text: str, reply_params=None) -> None:
+        """Send a plain text message with HTML fallback."""
+        try:
+            html = _markdown_to_telegram_html(text)
+            await self._app.bot.send_message(
+                chat_id=chat_id, text=html, parse_mode="HTML",
+                reply_parameters=reply_params,
+            )
+        except Exception as e:
+            logger.warning("HTML parse failed, falling back to plain text: {}", e)
+            try:
+                await self._app.bot.send_message(
+                    chat_id=chat_id, text=text, reply_parameters=reply_params,
+                )
+            except Exception as e2:
+                logger.error("Error sending Telegram message: {}", e2)
+
+    async def _send_with_streaming(self, chat_id: int, text: str, reply_params=None) -> None:
+        """Simulate streaming via send_message_draft, then persist with send_message."""
+        draft_id = int(time.time() * 1000) % (2**31)
+        try:
+            step = max(len(text) // 8, 40)
+            for i in range(step, len(text), step):
+                await self._app.bot.send_message_draft(
+                    chat_id=chat_id, draft_id=draft_id, text=text[:i],
+                )
+                await asyncio.sleep(0.04)
+            await self._app.bot.send_message_draft(
+                chat_id=chat_id, draft_id=draft_id, text=text,
+            )
+            await asyncio.sleep(0.15)
+        except Exception:
+            pass
+        await self._send_text(chat_id, text, reply_params)
 
     async def _on_start(self, update: Update, context: ContextTypes.DEFAULT_TYPE) -> None:
         """Handle /start command."""
diff --git a/nanobot/channels/whatsapp.py b/nanobot/channels/whatsapp.py
index 0d1ec7e..1307716 100644
--- a/nanobot/channels/whatsapp.py
+++ b/nanobot/channels/whatsapp.py
@@ -2,6 +2,7 @@
 
 import asyncio
 import json
+import mimetypes
 from collections import OrderedDict
 
 from loguru import logger
@@ -128,10 +129,22 @@ class WhatsAppChannel(BaseChannel):
                 logger.info("Voice message received from {}, but direct download from bridge is not yet supported.", sender_id)
                 content = "[Voice Message: Transcription not available for WhatsApp yet]"
 
+            # Extract media paths (images/documents/videos downloaded by the bridge)
+            media_paths = data.get("media") or []
+
+            # Build content tags matching Telegram's pattern: [image: /path] or [file: /path]
+            if media_paths:
+                for p in media_paths:
+                    mime, _ = mimetypes.guess_type(p)
+                    media_type = "image" if mime and mime.startswith("image/") else "file"
+                    media_tag = f"[{media_type}: {p}]"
+                    content = f"{content}\n{media_tag}" if content else media_tag
+
             await self._handle_message(
                 sender_id=sender_id,
                 chat_id=sender,  # Use full LID for replies
                 content=content,
+                media=media_paths,
                 metadata={
                     "message_id": message_id,
                     "timestamp": data.get("timestamp"),
diff --git a/nanobot/cli/commands.py b/nanobot/cli/commands.py
index 7d2c161..ca5d8d7 100644
--- a/nanobot/cli/commands.py
+++ b/nanobot/cli/commands.py
@@ -213,6 +213,7 @@ def onboard():
 def _make_provider(config: Config):
     """Create the appropriate LLM provider from config."""
     from nanobot.providers.openai_codex_provider import OpenAICodexProvider
+    from nanobot.providers.azure_openai_provider import AzureOpenAIProvider
 
     model = config.agents.defaults.model
     provider_name = config.get_provider_name(model)
@@ -231,6 +232,20 @@ def _make_provider(config: Config):
             default_model=model,
         )
 
+    # Azure OpenAI: direct Azure OpenAI endpoint with deployment name
+    if provider_name == "azure_openai":
+        if not p or not p.api_key or not p.api_base:
+            console.print("[red]Error: Azure OpenAI requires api_key and api_base.[/red]")
+            console.print("Set them in ~/.nanobot/config.json under providers.azure_openai section")
+            console.print("Use the model field to specify the deployment name.")
+            raise typer.Exit(1)
+        
+        return AzureOpenAIProvider(
+            api_key=p.api_key,
+            api_base=p.api_base,
+            default_model=model,
+        )
+
     from nanobot.providers.litellm_provider import LiteLLMProvider
     from nanobot.providers.registry import find_by_name
     spec = find_by_name(provider_name)
diff --git a/nanobot/config/schema.py b/nanobot/config/schema.py
index 2073eeb..803cb61 100644
--- a/nanobot/config/schema.py
+++ b/nanobot/config/schema.py
@@ -251,6 +251,7 @@ class ProvidersConfig(Base):
     """Configuration for LLM providers."""
 
     custom: ProviderConfig = Field(default_factory=ProviderConfig)  # Any OpenAI-compatible endpoint
+    azure_openai: ProviderConfig = Field(default_factory=ProviderConfig)  # Azure OpenAI (model = deployment name)
     anthropic: ProviderConfig = Field(default_factory=ProviderConfig)
     openai: ProviderConfig = Field(default_factory=ProviderConfig)
     openrouter: ProviderConfig = Field(default_factory=ProviderConfig)
diff --git a/nanobot/providers/__init__.py b/nanobot/providers/__init__.py
index b2bb2b9..5bd06f9 100644
--- a/nanobot/providers/__init__.py
+++ b/nanobot/providers/__init__.py
@@ -3,5 +3,6 @@
 from nanobot.providers.base import LLMProvider, LLMResponse
 from nanobot.providers.litellm_provider import LiteLLMProvider
 from nanobot.providers.openai_codex_provider import OpenAICodexProvider
+from nanobot.providers.azure_openai_provider import AzureOpenAIProvider
 
-__all__ = ["LLMProvider", "LLMResponse", "LiteLLMProvider", "OpenAICodexProvider"]
+__all__ = ["LLMProvider", "LLMResponse", "LiteLLMProvider", "OpenAICodexProvider", "AzureOpenAIProvider"]
diff --git a/nanobot/providers/azure_openai_provider.py b/nanobot/providers/azure_openai_provider.py
new file mode 100644
index 0000000..bd79b00
--- /dev/null
+++ b/nanobot/providers/azure_openai_provider.py
@@ -0,0 +1,210 @@
+"""Azure OpenAI provider implementation with API version 2024-10-21."""
+
+from __future__ import annotations
+
+import uuid
+from typing import Any
+from urllib.parse import urljoin
+
+import httpx
+import json_repair
+
+from nanobot.providers.base import LLMProvider, LLMResponse, ToolCallRequest
+
+_AZURE_MSG_KEYS = frozenset({"role", "content", "tool_calls", "tool_call_id", "name"})
+
+
+class AzureOpenAIProvider(LLMProvider):
+    """
+    Azure OpenAI provider with API version 2024-10-21 compliance.
+    
+    Features:
+    - Hardcoded API version 2024-10-21
+    - Uses model field as Azure deployment name in URL path
+    - Uses api-key header instead of Authorization Bearer
+    - Uses max_completion_tokens instead of max_tokens
+    - Direct HTTP calls, bypasses LiteLLM
+    """
+
+    def __init__(
+        self,
+        api_key: str = "",
+        api_base: str = "",
+        default_model: str = "gpt-5.2-chat",
+    ):
+        super().__init__(api_key, api_base)
+        self.default_model = default_model
+        self.api_version = "2024-10-21"
+        
+        # Validate required parameters
+        if not api_key:
+            raise ValueError("Azure OpenAI api_key is required")
+        if not api_base:
+            raise ValueError("Azure OpenAI api_base is required")
+        
+        # Ensure api_base ends with /
+        if not api_base.endswith('/'):
+            api_base += '/'
+        self.api_base = api_base
+
+    def _build_chat_url(self, deployment_name: str) -> str:
+        """Build the Azure OpenAI chat completions URL."""
+        # Azure OpenAI URL format:
+        # https://{resource}.openai.azure.com/openai/deployments/{deployment}/chat/completions?api-version={version}
+        base_url = self.api_base
+        if not base_url.endswith('/'):
+            base_url += '/'
+        
+        url = urljoin(
+            base_url, 
+            f"openai/deployments/{deployment_name}/chat/completions"
+        )
+        return f"{url}?api-version={self.api_version}"
+
+    def _build_headers(self) -> dict[str, str]:
+        """Build headers for Azure OpenAI API with api-key header."""
+        return {
+            "Content-Type": "application/json",
+            "api-key": self.api_key,  # Azure OpenAI uses api-key header, not Authorization
+            "x-session-affinity": uuid.uuid4().hex,  # For cache locality
+        }
+
+    @staticmethod
+    def _supports_temperature(
+        deployment_name: str,
+        reasoning_effort: str | None = None,
+    ) -> bool:
+        """Return True when temperature is likely supported for this deployment."""
+        if reasoning_effort:
+            return False
+        name = deployment_name.lower()
+        return not any(token in name for token in ("gpt-5", "o1", "o3", "o4"))
+
+    def _prepare_request_payload(
+        self,
+        deployment_name: str,
+        messages: list[dict[str, Any]],
+        tools: list[dict[str, Any]] | None = None,
+        max_tokens: int = 4096,
+        temperature: float = 0.7,
+        reasoning_effort: str | None = None,
+    ) -> dict[str, Any]:
+        """Prepare the request payload with Azure OpenAI 2024-10-21 compliance."""
+        payload: dict[str, Any] = {
+            "messages": self._sanitize_request_messages(
+                self._sanitize_empty_content(messages),
+                _AZURE_MSG_KEYS,
+            ),
+            "max_completion_tokens": max(1, max_tokens),  # Azure API 2024-10-21 uses max_completion_tokens
+        }
+
+        if self._supports_temperature(deployment_name, reasoning_effort):
+            payload["temperature"] = temperature
+
+        if reasoning_effort:
+            payload["reasoning_effort"] = reasoning_effort
+
+        if tools:
+            payload["tools"] = tools
+            payload["tool_choice"] = "auto"
+
+        return payload
+
+    async def chat(
+        self,
+        messages: list[dict[str, Any]],
+        tools: list[dict[str, Any]] | None = None,
+        model: str | None = None,
+        max_tokens: int = 4096,
+        temperature: float = 0.7,
+        reasoning_effort: str | None = None,
+    ) -> LLMResponse:
+        """
+        Send a chat completion request to Azure OpenAI.
+
+        Args:
+            messages: List of message dicts with 'role' and 'content'.
+            tools: Optional list of tool definitions in OpenAI format.
+            model: Model identifier (used as deployment name).
+            max_tokens: Maximum tokens in response (mapped to max_completion_tokens).
+            temperature: Sampling temperature.
+            reasoning_effort: Optional reasoning effort parameter.
+
+        Returns:
+            LLMResponse with content and/or tool calls.
+        """
+        deployment_name = model or self.default_model
+        url = self._build_chat_url(deployment_name)
+        headers = self._build_headers()
+        payload = self._prepare_request_payload(
+            deployment_name, messages, tools, max_tokens, temperature, reasoning_effort
+        )
+
+        try:
+            async with httpx.AsyncClient(timeout=60.0, verify=True) as client:
+                response = await client.post(url, headers=headers, json=payload)
+                if response.status_code != 200:
+                    return LLMResponse(
+                        content=f"Azure OpenAI API Error {response.status_code}: {response.text}",
+                        finish_reason="error",
+                    )
+                
+                response_data = response.json()
+                return self._parse_response(response_data)
+
+        except Exception as e:
+            return LLMResponse(
+                content=f"Error calling Azure OpenAI: {repr(e)}",
+                finish_reason="error",
+            )
+
+    def _parse_response(self, response: dict[str, Any]) -> LLMResponse:
+        """Parse Azure OpenAI response into our standard format."""
+        try:
+            choice = response["choices"][0]
+            message = choice["message"]
+
+            tool_calls = []
+            if message.get("tool_calls"):
+                for tc in message["tool_calls"]:
+                    # Parse arguments from JSON string if needed
+                    args = tc["function"]["arguments"]
+                    if isinstance(args, str):
+                        args = json_repair.loads(args)
+
+                    tool_calls.append(
+                        ToolCallRequest(
+                            id=tc["id"],
+                            name=tc["function"]["name"],
+                            arguments=args,
+                        )
+                    )
+
+            usage = {}
+            if response.get("usage"):
+                usage_data = response["usage"]
+                usage = {
+                    "prompt_tokens": usage_data.get("prompt_tokens", 0),
+                    "completion_tokens": usage_data.get("completion_tokens", 0),
+                    "total_tokens": usage_data.get("total_tokens", 0),
+                }
+
+            reasoning_content = message.get("reasoning_content") or None
+
+            return LLMResponse(
+                content=message.get("content"),
+                tool_calls=tool_calls,
+                finish_reason=choice.get("finish_reason", "stop"),
+                usage=usage,
+                reasoning_content=reasoning_content,
+            )
+
+        except (KeyError, IndexError) as e:
+            return LLMResponse(
+                content=f"Error parsing Azure OpenAI response: {str(e)}",
+                finish_reason="error",
+            )
+
+    def get_default_model(self) -> str:
+        """Get the default model (also used as default deployment name)."""
+        return self.default_model
\ No newline at end of file
diff --git a/nanobot/providers/base.py b/nanobot/providers/base.py
index 55bd805..0f73544 100644
--- a/nanobot/providers/base.py
+++ b/nanobot/providers/base.py
@@ -87,6 +87,20 @@ class LLMProvider(ABC):
             result.append(msg)
         return result
 
+    @staticmethod
+    def _sanitize_request_messages(
+        messages: list[dict[str, Any]],
+        allowed_keys: frozenset[str],
+    ) -> list[dict[str, Any]]:
+        """Keep only provider-safe message keys and normalize assistant content."""
+        sanitized = []
+        for msg in messages:
+            clean = {k: v for k, v in msg.items() if k in allowed_keys}
+            if clean.get("role") == "assistant" and "content" not in clean:
+                clean["content"] = None
+            sanitized.append(clean)
+        return sanitized
+
     @abstractmethod
     async def chat(
         self,
diff --git a/nanobot/providers/litellm_provider.py b/nanobot/providers/litellm_provider.py
index 620424e..cb67635 100644
--- a/nanobot/providers/litellm_provider.py
+++ b/nanobot/providers/litellm_provider.py
@@ -1,5 +1,6 @@
 """LiteLLM provider implementation for multi-provider support."""
 
+import hashlib
 import os
 import secrets
 import string
@@ -166,17 +167,43 @@ class LiteLLMProvider(LLMProvider):
             return _ANTHROPIC_EXTRA_KEYS
         return frozenset()
 
+    @staticmethod
+    def _normalize_tool_call_id(tool_call_id: Any) -> Any:
+        """Normalize tool_call_id to a provider-safe 9-char alphanumeric form."""
+        if not isinstance(tool_call_id, str):
+            return tool_call_id
+        if len(tool_call_id) == 9 and tool_call_id.isalnum():
+            return tool_call_id
+        return hashlib.sha1(tool_call_id.encode()).hexdigest()[:9]
+
     @staticmethod
     def _sanitize_messages(messages: list[dict[str, Any]], extra_keys: frozenset[str] = frozenset()) -> list[dict[str, Any]]:
         """Strip non-standard keys and ensure assistant messages have a content key."""
         allowed = _ALLOWED_MSG_KEYS | extra_keys
-        sanitized = []
-        for msg in messages:
-            clean = {k: v for k, v in msg.items() if k in allowed}
-            # Strict providers require "content" even when assistant only has tool_calls
-            if clean.get("role") == "assistant" and "content" not in clean:
-                clean["content"] = None
-            sanitized.append(clean)
+        sanitized = LLMProvider._sanitize_request_messages(messages, allowed)
+        id_map: dict[str, str] = {}
+
+        def map_id(value: Any) -> Any:
+            if not isinstance(value, str):
+                return value
+            return id_map.setdefault(value, LiteLLMProvider._normalize_tool_call_id(value))
+
+        for clean in sanitized:
+            # Keep assistant tool_calls[].id and tool tool_call_id in sync after
+            # shortening, otherwise strict providers reject the broken linkage.
+            if isinstance(clean.get("tool_calls"), list):
+                normalized_tool_calls = []
+                for tc in clean["tool_calls"]:
+                    if not isinstance(tc, dict):
+                        normalized_tool_calls.append(tc)
+                        continue
+                    tc_clean = dict(tc)
+                    tc_clean["id"] = map_id(tc_clean.get("id"))
+                    normalized_tool_calls.append(tc_clean)
+                clean["tool_calls"] = normalized_tool_calls
+
+            if "tool_call_id" in clean and clean["tool_call_id"]:
+                clean["tool_call_id"] = map_id(clean["tool_call_id"])
         return sanitized
 
     async def chat(
diff --git a/nanobot/providers/registry.py b/nanobot/providers/registry.py
index 59ba31a..3ba1a0e 100644
--- a/nanobot/providers/registry.py
+++ b/nanobot/providers/registry.py
@@ -79,6 +79,16 @@ PROVIDERS: tuple[ProviderSpec, ...] = (
         litellm_prefix="",
         is_direct=True,
     ),
+
+    # === Azure OpenAI (direct API calls with API version 2024-10-21) =====
+    ProviderSpec(
+        name="azure_openai",
+        keywords=("azure", "azure-openai"),
+        env_key="",
+        display_name="Azure OpenAI",
+        litellm_prefix="",
+        is_direct=True,
+    ),
     # === Gateways (detected by api_key / api_base, not model name) =========
     # Gateways can route any model, so they win in fallback.
     # OpenRouter: global gateway, keys start with "sk-or-"
diff --git a/tests/test_azure_openai_provider.py b/tests/test_azure_openai_provider.py
new file mode 100644
index 0000000..77f36d4
--- /dev/null
+++ b/tests/test_azure_openai_provider.py
@@ -0,0 +1,399 @@
+"""Test Azure OpenAI provider implementation (updated for model-based deployment names)."""
+
+from unittest.mock import AsyncMock, Mock, patch
+
+import pytest
+
+from nanobot.providers.azure_openai_provider import AzureOpenAIProvider
+from nanobot.providers.base import LLMResponse
+
+
+def test_azure_openai_provider_init():
+    """Test AzureOpenAIProvider initialization without deployment_name."""
+    provider = AzureOpenAIProvider(
+        api_key="test-key",
+        api_base="https://test-resource.openai.azure.com",
+        default_model="gpt-4o-deployment",
+    )
+    
+    assert provider.api_key == "test-key"
+    assert provider.api_base == "https://test-resource.openai.azure.com/"
+    assert provider.default_model == "gpt-4o-deployment"
+    assert provider.api_version == "2024-10-21"
+
+
+def test_azure_openai_provider_init_validation():
+    """Test AzureOpenAIProvider initialization validation."""
+    # Missing api_key
+    with pytest.raises(ValueError, match="Azure OpenAI api_key is required"):
+        AzureOpenAIProvider(api_key="", api_base="https://test.com")
+    
+    # Missing api_base
+    with pytest.raises(ValueError, match="Azure OpenAI api_base is required"):
+        AzureOpenAIProvider(api_key="test", api_base="")
+
+
+def test_build_chat_url():
+    """Test Azure OpenAI URL building with different deployment names."""
+    provider = AzureOpenAIProvider(
+        api_key="test-key",
+        api_base="https://test-resource.openai.azure.com",
+        default_model="gpt-4o",
+    )
+    
+    # Test various deployment names
+    test_cases = [
+        ("gpt-4o-deployment", "https://test-resource.openai.azure.com/openai/deployments/gpt-4o-deployment/chat/completions?api-version=2024-10-21"),
+        ("gpt-35-turbo", "https://test-resource.openai.azure.com/openai/deployments/gpt-35-turbo/chat/completions?api-version=2024-10-21"),
+        ("custom-model", "https://test-resource.openai.azure.com/openai/deployments/custom-model/chat/completions?api-version=2024-10-21"),
+    ]
+    
+    for deployment_name, expected_url in test_cases:
+        url = provider._build_chat_url(deployment_name)
+        assert url == expected_url
+
+
+def test_build_chat_url_api_base_without_slash():
+    """Test URL building when api_base doesn't end with slash."""
+    provider = AzureOpenAIProvider(
+        api_key="test-key",
+        api_base="https://test-resource.openai.azure.com",  # No trailing slash
+        default_model="gpt-4o",
+    )
+    
+    url = provider._build_chat_url("test-deployment")
+    expected = "https://test-resource.openai.azure.com/openai/deployments/test-deployment/chat/completions?api-version=2024-10-21"
+    assert url == expected
+
+
+def test_build_headers():
+    """Test Azure OpenAI header building with api-key authentication."""
+    provider = AzureOpenAIProvider(
+        api_key="test-api-key-123",
+        api_base="https://test-resource.openai.azure.com",
+        default_model="gpt-4o",
+    )
+    
+    headers = provider._build_headers()
+    assert headers["Content-Type"] == "application/json"
+    assert headers["api-key"] == "test-api-key-123"  # Azure OpenAI specific header
+    assert "x-session-affinity" in headers
+
+
+def test_prepare_request_payload():
+    """Test request payload preparation with Azure OpenAI 2024-10-21 compliance."""
+    provider = AzureOpenAIProvider(
+        api_key="test-key",
+        api_base="https://test-resource.openai.azure.com",
+        default_model="gpt-4o",
+    )
+    
+    messages = [{"role": "user", "content": "Hello"}]
+    payload = provider._prepare_request_payload("gpt-4o", messages, max_tokens=1500, temperature=0.8)
+    
+    assert payload["messages"] == messages
+    assert payload["max_completion_tokens"] == 1500  # Azure API 2024-10-21 uses max_completion_tokens
+    assert payload["temperature"] == 0.8
+    assert "tools" not in payload
+    
+    # Test with tools
+    tools = [{"type": "function", "function": {"name": "get_weather", "parameters": {}}}]
+    payload_with_tools = provider._prepare_request_payload("gpt-4o", messages, tools=tools)
+    assert payload_with_tools["tools"] == tools
+    assert payload_with_tools["tool_choice"] == "auto"
+    
+    # Test with reasoning_effort
+    payload_with_reasoning = provider._prepare_request_payload(
+        "gpt-5-chat", messages, reasoning_effort="medium"
+    )
+    assert payload_with_reasoning["reasoning_effort"] == "medium"
+    assert "temperature" not in payload_with_reasoning
+
+
+def test_prepare_request_payload_sanitizes_messages():
+    """Test Azure payload strips non-standard message keys before sending."""
+    provider = AzureOpenAIProvider(
+        api_key="test-key",
+        api_base="https://test-resource.openai.azure.com",
+        default_model="gpt-4o",
+    )
+
+    messages = [
+        {
+            "role": "assistant",
+            "tool_calls": [{"id": "call_123", "type": "function", "function": {"name": "x"}}],
+            "reasoning_content": "hidden chain-of-thought",
+        },
+        {
+            "role": "tool",
+            "tool_call_id": "call_123",
+            "name": "x",
+            "content": "ok",
+            "extra_field": "should be removed",
+        },
+    ]
+
+    payload = provider._prepare_request_payload("gpt-4o", messages)
+
+    assert payload["messages"] == [
+        {
+            "role": "assistant",
+            "content": None,
+            "tool_calls": [{"id": "call_123", "type": "function", "function": {"name": "x"}}],
+        },
+        {
+            "role": "tool",
+            "tool_call_id": "call_123",
+            "name": "x",
+            "content": "ok",
+        },
+    ]
+
+
+@pytest.mark.asyncio
+async def test_chat_success():
+    """Test successful chat request using model as deployment name."""
+    provider = AzureOpenAIProvider(
+        api_key="test-key",
+        api_base="https://test-resource.openai.azure.com",
+        default_model="gpt-4o-deployment",
+    )
+    
+    # Mock response data
+    mock_response_data = {
+        "choices": [{
+            "message": {
+                "content": "Hello! How can I help you today?",
+                "role": "assistant"
+            },
+            "finish_reason": "stop"
+        }],
+        "usage": {
+            "prompt_tokens": 12,
+            "completion_tokens": 18,
+            "total_tokens": 30
+        }
+    }
+    
+    with patch("httpx.AsyncClient") as mock_client:
+        mock_response = AsyncMock()
+        mock_response.status_code = 200
+        mock_response.json = Mock(return_value=mock_response_data)
+        
+        mock_context = AsyncMock()
+        mock_context.post = AsyncMock(return_value=mock_response)
+        mock_client.return_value.__aenter__.return_value = mock_context
+        
+        # Test with specific model (deployment name)
+        messages = [{"role": "user", "content": "Hello"}]
+        result = await provider.chat(messages, model="custom-deployment")
+        
+        assert isinstance(result, LLMResponse)
+        assert result.content == "Hello! How can I help you today?"
+        assert result.finish_reason == "stop"
+        assert result.usage["prompt_tokens"] == 12
+        assert result.usage["completion_tokens"] == 18
+        assert result.usage["total_tokens"] == 30
+        
+        # Verify URL was built with the provided model as deployment name
+        call_args = mock_context.post.call_args
+        expected_url = "https://test-resource.openai.azure.com/openai/deployments/custom-deployment/chat/completions?api-version=2024-10-21"
+        assert call_args[0][0] == expected_url
+
+
+@pytest.mark.asyncio
+async def test_chat_uses_default_model_when_no_model_provided():
+    """Test that chat uses default_model when no model is specified."""
+    provider = AzureOpenAIProvider(
+        api_key="test-key",
+        api_base="https://test-resource.openai.azure.com",
+        default_model="default-deployment",
+    )
+    
+    mock_response_data = {
+        "choices": [{
+            "message": {"content": "Response", "role": "assistant"},
+            "finish_reason": "stop"
+        }],
+        "usage": {"prompt_tokens": 5, "completion_tokens": 5, "total_tokens": 10}
+    }
+    
+    with patch("httpx.AsyncClient") as mock_client:
+        mock_response = AsyncMock()
+        mock_response.status_code = 200
+        mock_response.json = Mock(return_value=mock_response_data)
+        
+        mock_context = AsyncMock()
+        mock_context.post = AsyncMock(return_value=mock_response)
+        mock_client.return_value.__aenter__.return_value = mock_context
+        
+        messages = [{"role": "user", "content": "Test"}]
+        await provider.chat(messages)  # No model specified
+        
+        # Verify URL was built with default model as deployment name
+        call_args = mock_context.post.call_args
+        expected_url = "https://test-resource.openai.azure.com/openai/deployments/default-deployment/chat/completions?api-version=2024-10-21"
+        assert call_args[0][0] == expected_url
+
+
+@pytest.mark.asyncio
+async def test_chat_with_tool_calls():
+    """Test chat request with tool calls in response."""
+    provider = AzureOpenAIProvider(
+        api_key="test-key",
+        api_base="https://test-resource.openai.azure.com",
+        default_model="gpt-4o",
+    )
+    
+    # Mock response with tool calls
+    mock_response_data = {
+        "choices": [{
+            "message": {
+                "content": None,
+                "role": "assistant",
+                "tool_calls": [{
+                    "id": "call_12345",
+                    "function": {
+                        "name": "get_weather",
+                        "arguments": '{"location": "San Francisco"}'
+                    }
+                }]
+            },
+            "finish_reason": "tool_calls"
+        }],
+        "usage": {
+            "prompt_tokens": 20,
+            "completion_tokens": 15,
+            "total_tokens": 35
+        }
+    }
+    
+    with patch("httpx.AsyncClient") as mock_client:
+        mock_response = AsyncMock()
+        mock_response.status_code = 200
+        mock_response.json = Mock(return_value=mock_response_data)
+        
+        mock_context = AsyncMock()
+        mock_context.post = AsyncMock(return_value=mock_response)
+        mock_client.return_value.__aenter__.return_value = mock_context
+        
+        messages = [{"role": "user", "content": "What's the weather?"}]
+        tools = [{"type": "function", "function": {"name": "get_weather", "parameters": {}}}]
+        result = await provider.chat(messages, tools=tools, model="weather-model")
+        
+        assert isinstance(result, LLMResponse)
+        assert result.content is None
+        assert result.finish_reason == "tool_calls"
+        assert len(result.tool_calls) == 1
+        assert result.tool_calls[0].name == "get_weather"
+        assert result.tool_calls[0].arguments == {"location": "San Francisco"}
+
+
+@pytest.mark.asyncio
+async def test_chat_api_error():
+    """Test chat request API error handling."""
+    provider = AzureOpenAIProvider(
+        api_key="test-key",
+        api_base="https://test-resource.openai.azure.com",
+        default_model="gpt-4o",
+    )
+    
+    with patch("httpx.AsyncClient") as mock_client:
+        mock_response = AsyncMock()
+        mock_response.status_code = 401
+        mock_response.text = "Invalid authentication credentials"
+        
+        mock_context = AsyncMock()
+        mock_context.post = AsyncMock(return_value=mock_response)
+        mock_client.return_value.__aenter__.return_value = mock_context
+        
+        messages = [{"role": "user", "content": "Hello"}]
+        result = await provider.chat(messages)
+        
+        assert isinstance(result, LLMResponse)
+        assert "Azure OpenAI API Error 401" in result.content
+        assert "Invalid authentication credentials" in result.content
+        assert result.finish_reason == "error"
+
+
+@pytest.mark.asyncio
+async def test_chat_connection_error():
+    """Test chat request connection error handling."""
+    provider = AzureOpenAIProvider(
+        api_key="test-key",
+        api_base="https://test-resource.openai.azure.com",
+        default_model="gpt-4o",
+    )
+    
+    with patch("httpx.AsyncClient") as mock_client:
+        mock_context = AsyncMock()
+        mock_context.post = AsyncMock(side_effect=Exception("Connection failed"))
+        mock_client.return_value.__aenter__.return_value = mock_context
+        
+        messages = [{"role": "user", "content": "Hello"}]
+        result = await provider.chat(messages)
+        
+        assert isinstance(result, LLMResponse)
+        assert "Error calling Azure OpenAI: Exception('Connection failed')" in result.content
+        assert result.finish_reason == "error"
+
+
+def test_parse_response_malformed():
+    """Test response parsing with malformed data."""
+    provider = AzureOpenAIProvider(
+        api_key="test-key",
+        api_base="https://test-resource.openai.azure.com",
+        default_model="gpt-4o",
+    )
+    
+    # Test with missing choices
+    malformed_response = {"usage": {"prompt_tokens": 10}}
+    result = provider._parse_response(malformed_response)
+    
+    assert isinstance(result, LLMResponse)
+    assert "Error parsing Azure OpenAI response" in result.content
+    assert result.finish_reason == "error"
+
+
+def test_get_default_model():
+    """Test get_default_model method."""
+    provider = AzureOpenAIProvider(
+        api_key="test-key",
+        api_base="https://test-resource.openai.azure.com",
+        default_model="my-custom-deployment",
+    )
+    
+    assert provider.get_default_model() == "my-custom-deployment"
+
+
+if __name__ == "__main__":
+    # Run basic tests
+    print("Running basic Azure OpenAI provider tests...")
+    
+    # Test initialization
+    provider = AzureOpenAIProvider(
+        api_key="test-key",
+        api_base="https://test-resource.openai.azure.com",
+        default_model="gpt-4o-deployment",
+    )
+    print("✅ Provider initialization successful")
+    
+    # Test URL building
+    url = provider._build_chat_url("my-deployment")
+    expected = "https://test-resource.openai.azure.com/openai/deployments/my-deployment/chat/completions?api-version=2024-10-21"
+    assert url == expected
+    print("✅ URL building works correctly")
+    
+    # Test headers
+    headers = provider._build_headers()
+    assert headers["api-key"] == "test-key"
+    assert headers["Content-Type"] == "application/json"
+    print("✅ Header building works correctly")
+    
+    # Test payload preparation
+    messages = [{"role": "user", "content": "Test"}]
+    payload = provider._prepare_request_payload("gpt-4o-deployment", messages, max_tokens=1000)
+    assert payload["max_completion_tokens"] == 1000  # Azure 2024-10-21 format
+    print("✅ Payload preparation works correctly")
+    
+    print("✅ All basic tests passed! Updated test file is working correctly.")
\ No newline at end of file