diff --git a/src/agents/agents.test.ts b/src/agents/agents.test.ts
index 1d55da210..7708aa004 100644
--- a/src/agents/agents.test.ts
+++ b/src/agents/agents.test.ts
@@ -39,6 +39,38 @@ describe("agent buildArgs + parseOutput helpers", () => {
     expect(builtNoIdentity.at(-1)).not.toContain(CLAUDE_IDENTITY_PREFIX);
   });
 
+  it("claudeSpec prepends identity even when body is empty (e.g. /new)", () => {
+    // This is the /new reset trigger case - body is empty after reset trigger is stripped
+    const argv = ["claude", ""];
+    const built = claudeSpec.buildArgs({
+      argv,
+      bodyIndex: 1,
+      isNewSession: true,
+      sessionId: "sess",
+      sendSystemOnce: true,
+      systemSent: false,
+      identityPrefix: "Custom session intro here",
+      format: "json",
+    });
+
+    // Should still prepend the identity prefix even though body is empty
+    const lastArg = built.at(-1);
+    expect(lastArg).toContain("Custom session intro here");
+
+    // Verify it doesn't prepend identity when systemSent is true
+    const builtAfterSystem = claudeSpec.buildArgs({
+      argv,
+      bodyIndex: 1,
+      isNewSession: false,
+      sessionId: "sess",
+      sendSystemOnce: true,
+      systemSent: true,
+      identityPrefix: "Custom session intro here",
+      format: "json",
+    });
+    expect(builtAfterSystem.at(-1)).toBe("");
+  });
+
   it("opencodeSpec adds format flag and identity prefix when needed", () => {
     const argv = ["opencode", "body"];
     const built = opencodeSpec.buildArgs({
diff --git a/src/agents/claude.ts b/src/agents/claude.ts
index 22f8e7ed6..3db224221 100644
--- a/src/agents/claude.ts
+++ b/src/agents/claude.ts
@@ -55,13 +55,12 @@ export const claudeSpec: AgentSpec = {
       beforeBody.push("-p");
     }
 
-    const shouldPrependIdentity = !(ctx.sendSystemOnce && ctx.systemSent);
-    const bodyWithIdentity =
-      shouldPrependIdentity && body
-        ? [ctx.identityPrefix ?? CLAUDE_IDENTITY_PREFIX, body]
-            .filter(Boolean)
-            .join("\n\n")
-        : body;
+    const shouldPrependIdentity = ctx.isNewSession || !(ctx.sendSystemOnce && ctx.systemSent);
+    const bodyWithIdentity = shouldPrependIdentity
+      ? [ctx.identityPrefix ?? CLAUDE_IDENTITY_PREFIX, body]
+          .filter(Boolean)
+          .join("\n\n")
+      : body;
 
     return [...beforeBody, bodyWithIdentity, ...afterBody];
   },
diff --git a/src/agents/gemini.ts b/src/agents/gemini.ts
index ce0d68165..10ab48289 100644
--- a/src/agents/gemini.ts
+++ b/src/agents/gemini.ts
@@ -40,7 +40,7 @@ export const geminiSpec: AgentSpec = {
       }
     }
 
-    const shouldPrependIdentity = !(ctx.sendSystemOnce && ctx.systemSent);
+    const shouldPrependIdentity = ctx.isNewSession || !(ctx.sendSystemOnce && ctx.systemSent);
     const bodyWithIdentity =
       shouldPrependIdentity && body
         ? [ctx.identityPrefix ?? GEMINI_IDENTITY_PREFIX, body]
diff --git a/src/agents/opencode.ts b/src/agents/opencode.ts
index 836b7c4e0..e33708301 100644
--- a/src/agents/opencode.ts
+++ b/src/agents/opencode.ts
@@ -41,7 +41,7 @@ export const opencodeSpec: AgentSpec = {
     // Identity prefix
     // Opencode streams text tokens; we still seed an identity so the agent
     // keeps context on first turn.
-    const shouldPrependIdentity = !(ctx.sendSystemOnce && ctx.systemSent);
+    const shouldPrependIdentity = ctx.isNewSession || !(ctx.sendSystemOnce && ctx.systemSent);
     const bodyWithIdentity =
       shouldPrependIdentity && body
         ? [ctx.identityPrefix ?? OPENCODE_IDENTITY_PREFIX, body]
diff --git a/src/agents/pi.ts b/src/agents/pi.ts
index 195315ffc..629e1ee18 100644
--- a/src/agents/pi.ts
+++ b/src/agents/pi.ts
@@ -158,7 +158,8 @@ export const piSpec: AgentSpec = {
     }
     // Session defaults
     // Identity prefix optional; Pi usually doesn't need it, but allow injection
-    if (!(ctx.sendSystemOnce && ctx.systemSent) && argv[ctx.bodyIndex]) {
+    const shouldPrependIdentity = ctx.isNewSession || !(ctx.sendSystemOnce && ctx.systemSent);
+    if (shouldPrependIdentity && argv[ctx.bodyIndex]) {
       const existingBody = argv[ctx.bodyIndex];
       argv[ctx.bodyIndex] = [ctx.identityPrefix, existingBody]
         .filter(Boolean)
diff --git a/src/auto-reply/command-reply.ts b/src/auto-reply/command-reply.ts
index 6eecb945a..5dd77ff93 100644
--- a/src/auto-reply/command-reply.ts
+++ b/src/auto-reply/command-reply.ts
@@ -36,6 +36,7 @@ type CommandReplyParams = {
   isNewSession: boolean;
   isFirstTurnInSession: boolean;
   systemSent: boolean;
+  sessionIntro?: string;
   timeoutMs: number;
   timeoutSeconds: number;
   commandRunner: typeof runCommandWithTimeout;
@@ -288,6 +289,7 @@ export async function runCommandReply(
     isNewSession,
     isFirstTurnInSession,
     systemSent,
+    sessionIntro,
     timeoutMs,
     timeoutSeconds,
     commandRunner,
@@ -392,7 +394,7 @@ export async function runCommandReply(
         sessionId: templatingCtx.SessionId,
         sendSystemOnce,
         systemSent,
-        identityPrefix: agentCfg.identityPrefix,
+        identityPrefix: agentCfg.identityPrefix ?? sessionIntro,
         format: agentCfg.format,
       })
     : argv;
diff --git a/src/auto-reply/reply.ts b/src/auto-reply/reply.ts
index a425cd321..056a062ad 100644
--- a/src/auto-reply/reply.ts
+++ b/src/auto-reply/reply.ts
@@ -471,9 +471,10 @@ export async function getReplyFromConfig(
   // Optional prefix injected before Body for templating/command prompts.
   const sendSystemOnce = sessionCfg?.sendSystemOnce === true;
   const isFirstTurnInSession = isNewSession || !systemSent;
+  const sessionIntroConfig = sessionCfg?.sessionIntro;
   const sessionIntro =
-    isFirstTurnInSession && sessionCfg?.sessionIntro
-      ? applyTemplate(sessionCfg.sessionIntro, sessionCtx)
+    isFirstTurnInSession && sessionIntroConfig
+      ? applyTemplate(sessionIntroConfig, sessionCtx)
       : "";
   const groupIntro =
     isFirstTurnInSession && sessionCtx.ChatType === "group"
@@ -497,7 +498,19 @@ export async function getReplyFromConfig(
   const bodyPrefix = reply?.bodyPrefix
     ? applyTemplate(reply.bodyPrefix, sessionCtx)
     : "";
-  const baseBody = sessionCtx.BodyStripped ?? sessionCtx.Body ?? "";
+  let baseBody = sessionCtx.BodyStripped ?? sessionCtx.Body ?? "";
+
+  // Extract stray think level token from user's message BEFORE adding prefixes
+  // (to avoid removing "Think" from bodyPrefix like "Think deeply whenever asked.")
+  if (!resolvedThinkLevel && baseBody) {
+    const parts = baseBody.split(/\s+/);
+    const maybeLevel = normalizeThinkLevel(parts[0]);
+    if (maybeLevel) {
+      resolvedThinkLevel = maybeLevel;
+      baseBody = parts.slice(1).join(" ").trim();
+    }
+  }
+
   const abortedHint =
     reply?.mode === "command" && abortedLastRun
       ? "Note: The previous agent run was aborted by the user. Resume carefully or ask for clarification."
@@ -562,22 +575,13 @@ export async function getReplyFromConfig(
     mediaNote && reply?.mode === "command"
       ? "To send an image back, add a line like: MEDIA:https://example.com/image.jpg (no spaces). Keep caption in the text body."
       : undefined;
-  let commandBody = mediaNote
+  const commandBody = mediaNote
     ? [mediaNote, mediaReplyHint, prefixedBody ?? ""]
         .filter(Boolean)
         .join("\n")
         .trim()
     : prefixedBody;
 
-  // Fallback: if a stray leading level token remains, consume it
-  if (!resolvedThinkLevel && commandBody) {
-    const parts = commandBody.split(/\s+/);
-    const maybeLevel = normalizeThinkLevel(parts[0]);
-    if (maybeLevel) {
-      resolvedThinkLevel = maybeLevel;
-      commandBody = parts.slice(1).join(" ").trim();
-    }
-  }
   const templatingCtx: TemplateContext = {
     ...sessionCtx,
     Body: commandBody,
@@ -629,6 +633,7 @@ export async function getReplyFromConfig(
         isNewSession,
         isFirstTurnInSession,
         systemSent,
+        sessionIntro,
         timeoutMs,
         timeoutSeconds,
         commandRunner,
diff --git a/src/cli/multi-relay.test.ts b/src/cli/multi-relay.test.ts
index d4a9831b0..c9d655101 100644
--- a/src/cli/multi-relay.test.ts
+++ b/src/cli/multi-relay.test.ts
@@ -126,7 +126,7 @@ describe("runMultiProviderRelay", () => {
 			undefined,
 			mockRuntime,
 			expect.any(AbortSignal),
-			webTuning,
+			{ ...webTuning, suppressStartMessage: true },
 		);
 	});
 
diff --git a/src/config/config.ts b/src/config/config.ts
index a34a928cc..d35a0bea7 100644
--- a/src/config/config.ts
+++ b/src/config/config.ts
@@ -43,10 +43,6 @@ export type WebConfig = {
   reconnect?: WebReconnectConfig;
 };
 
-export type TelegramConfig = {
-  allowFrom?: string[]; // @username or user IDs
-};
-
 export type GroupChatConfig = {
   requireMention?: boolean;
   mentionPatterns?: string[];
@@ -90,7 +86,6 @@ export type WarelayConfig = {
     };
   };
   web?: WebConfig;
-  telegram?: TelegramConfig;
 };
 
 // New branding path (preferred)
diff --git a/src/telegram/monitor.test.ts b/src/telegram/monitor.test.ts
index 52f78d0f5..9fbb9e588 100644
--- a/src/telegram/monitor.test.ts
+++ b/src/telegram/monitor.test.ts
@@ -26,10 +26,8 @@ vi.mock("../env.js", () => ({
 
 vi.mock("../config/config.js", () => ({
   loadConfig: vi.fn(() => ({
-    telegram: {
-      allowFrom: ["@testuser"],
-    },
     inbound: {
+      allowFrom: ["@testuser"],
       reply: {
         mode: "text",
         text: "Auto-reply test",
@@ -207,10 +205,8 @@ describe("monitorTelegramProvider", () => {
 
     // Set allowFrom filter
     (loadConfig as Mock).mockReturnValueOnce({
-      telegram: {
-        allowFrom: ["@alloweduser"],
-      },
       inbound: {
+        allowFrom: ["@alloweduser"],
         reply: {
           mode: "text",
           text: "Auto-reply test",
diff --git a/src/telegram/monitor.ts b/src/telegram/monitor.ts
index 75113b284..4ff7a6d96 100644
--- a/src/telegram/monitor.ts
+++ b/src/telegram/monitor.ts
@@ -22,12 +22,37 @@ import { normalizeAllowFromEntry } from "../utils.js";
 
 const TELEGRAM_TEXT_LIMIT = 4096; // Telegram's message length limit
 
+/**
+ * Format timestamp in the same format as WhatsApp relay.
+ * Example: [Dec 5 22:41]
+ */
+function formatTimestamp(ts: number, config?: ReturnType<typeof loadConfig>): string {
+  const tsCfg = config?.inbound?.timestampPrefix;
+  const tsEnabled = tsCfg !== false; // default true
+  if (!tsEnabled) return "";
+  const tz = typeof tsCfg === "string" ? tsCfg : "UTC";
+  const date = new Date(ts);
+  try {
+    return `[${date.toLocaleDateString("en-US", { month: "short", day: "numeric", timeZone: tz })} ${date.toLocaleTimeString("en-US", { hour: "2-digit", minute: "2-digit", hour12: false, timeZone: tz })}] `;
+  } catch {
+    return `[${date.toISOString().slice(5, 16).replace("T", " ")}] `;
+  }
+}
+
 /**
  * Convert ProviderMessage to MsgContext for auto-reply system.
  */
-function providerMessageToContext(message: ProviderMessage): MsgContext {
+function providerMessageToContext(
+  message: ProviderMessage,
+  config?: ReturnType<typeof loadConfig>,
+): MsgContext {
+  const timestampPrefix = formatTimestamp(message.timestamp, config);
+  const bodyWithTimestamp = timestampPrefix
+    ? `${timestampPrefix}${message.body}`
+    : message.body;
+
   return {
-    Body: message.body,
+    Body: bodyWithTimestamp,
     From: message.from,
     To: message.to,
     MessageSid: message.id,
@@ -68,10 +93,13 @@ async function sendReply(
         media: firstMedia ? [{ type: "image", url: firstMedia }] : undefined,
       });
 
+      // Log the reply text
+      runtime.log(`↩️  ${firstChunk}`);
+
       if (isVerbose()) {
         runtime.log(
           success(
-            `↩️  Auto-replied to ${replyTo} via Telegram (id ${result.messageId})`,
+            `Auto-replied to ${replyTo} via Telegram (id ${result.messageId})`,
           ),
         );
       }
@@ -85,6 +113,7 @@ async function sendReply(
   for (let i = 1; i < chunks.length; i++) {
     try {
       await provider.send(replyTo, chunks[i]);
+      runtime.log(`↩️  ${chunks[i]}`);
     } catch (err) {
       runtime.error(
         danger(`Failed to send Telegram reply chunk ${i}: ${String(err)}`),
@@ -114,11 +143,11 @@ async function handleInboundMessage(
   provider: Provider,
   runtime: RuntimeEnv,
 ): Promise<void> {
-  const ctx = providerMessageToContext(message);
   const config = loadConfig();
+  const ctx = providerMessageToContext(message, config);
 
   // Check allowFrom filter
-  const allowFrom = config.telegram?.allowFrom;
+  const allowFrom = config.inbound?.allowFrom;
   if (Array.isArray(allowFrom) && allowFrom.length > 0) {
     if (!allowFrom.includes("*")) {
       const normalizedFrom = normalizeAllowFromEntry(message.from, "telegram");
@@ -128,7 +157,7 @@ async function handleInboundMessage(
       if (!normalizedAllowList.includes(normalizedFrom)) {
         if (isVerbose()) {
           logVerbose(
-            `Skipping auto-reply: sender ${message.from} not in telegram.allowFrom list`,
+            `Skipping auto-reply: sender ${message.from} not in allowFrom list`,
           );
         }
         return;
@@ -137,9 +166,9 @@ async function handleInboundMessage(
   }
 
   // Log inbound message
-  const timestamp = new Date(message.timestamp).toISOString();
+  const formattedTs = formatTimestamp(message.timestamp, config);
   runtime.log(
-    `\n[${timestamp}] ${message.from} -> ${message.to}: ${message.body}`,
+    `\n${formattedTs}${message.from} -> ${message.to}: ${message.body}`,
   );
 
   // Get reply from config
@@ -209,7 +238,7 @@ export async function monitorTelegramProvider(
     apiId: Number.parseInt(env.telegram.apiId, 10),
     apiHash: env.telegram.apiHash,
     sessionDir: undefined, // Uses default ~/.warelay/telegram
-    allowFrom: config.telegram?.allowFrom,
+    allowFrom: config.inbound?.allowFrom,
     verbose,
   };