diff --git a/cloudflare-gastown/container/src/control-server.ts b/cloudflare-gastown/container/src/control-server.ts
index 70ba58c62..5834a1b81 100644
--- a/cloudflare-gastown/container/src/control-server.ts
+++ b/cloudflare-gastown/container/src/control-server.ts
@@ -220,6 +220,7 @@ app.patch('/agents/:agentId/model', async c => {
       ['github_cli_pat', 'GITHUB_CLI_PAT'],
       ['git_author_name', 'GASTOWN_GIT_AUTHOR_NAME'],
       ['git_author_email', 'GASTOWN_GIT_AUTHOR_EMAIL'],
+      ['kilocode_token', 'KILOCODE_TOKEN'],
     ];
     for (const [cfgKey, envKey] of CONFIG_ENV_MAP) {
       const val = cfg[cfgKey];
diff --git a/cloudflare-gastown/container/src/process-manager.ts b/cloudflare-gastown/container/src/process-manager.ts
index f0008e320..6b9d390ba 100644
--- a/cloudflare-gastown/container/src/process-manager.ts
+++ b/cloudflare-gastown/container/src/process-manager.ts
@@ -843,6 +843,7 @@ export async function updateAgentModel(
     'GASTOWN_GIT_AUTHOR_NAME',
     'GASTOWN_GIT_AUTHOR_EMAIL',
     'GASTOWN_DISABLE_AI_COAUTHOR',
+    'KILOCODE_TOKEN',
   ]);
   const hotSwapEnv: Record<string, string> = {};
   for (const [key, value] of Object.entries(agent.startupEnv)) {
diff --git a/cloudflare-gastown/src/dos/Town.do.ts b/cloudflare-gastown/src/dos/Town.do.ts
index b3eeaa158..5124e0a0d 100644
--- a/cloudflare-gastown/src/dos/Town.do.ts
+++ b/cloudflare-gastown/src/dos/Town.do.ts
@@ -56,6 +56,8 @@ import { query } from '../util/query.util';
 import { getAgentDOStub } from './Agent.do';
 import { getTownContainerStub } from './TownContainer.do';
 
+import { generateKiloApiToken } from '../util/kilo-token.util';
+import { resolveSecret } from '../util/secret.util';
 import { writeEvent, type GastownEventData } from '../util/analytics.util';
 import { logger, withLogTags } from '../util/log.util';
 import { BeadPriority } from '../types';
@@ -616,6 +618,7 @@ export class TownDO extends DurableObject<Env> {
       ['GASTOWN_GIT_AUTHOR_NAME', townConfig.git_author_name],
       ['GASTOWN_GIT_AUTHOR_EMAIL', townConfig.git_author_email],
       ['GASTOWN_DISABLE_AI_COAUTHOR', townConfig.disable_ai_coauthor ? '1' : undefined],
+      ['KILOCODE_TOKEN', townConfig.kilocode_token],
     ];
 
     for (const [key, value] of envMapping) {
@@ -3014,6 +3017,16 @@ export class TownDO extends DurableObject<Env> {
           error: err instanceof Error ? err.message : String(err),
         });
       }
+
+      // Proactively remint KILOCODE_TOKEN before it expires (30-day
+      // expiry, checked daily, refreshed within 7 days of expiry).
+      try {
+        await this.refreshKilocodeTokenIfExpiring();
+      } catch (err) {
+        logger.warn('alarm: refreshKilocodeTokenIfExpiring failed', {
+          error: err instanceof Error ? err.message : String(err),
+        });
+      }
     }
 
     // ── Pre-phase: Observe container status for working agents ────────
@@ -3299,6 +3312,78 @@ export class TownDO extends DurableObject<Env> {
     this.lastContainerTokenRefreshAt = now;
   }
 
+  /**
+   * Proactively remint KILOCODE_TOKEN when it's approaching expiry.
+   * Throttled to once per day — the 30-day token is refreshed when
+   * within 7 days of expiry, providing ample safety margin.
+   *
+   * Decodes the existing JWT payload to extract user identity (no
+   * signature verification needed — we're just reading the claims to
+   * re-sign with the same data).
+   */
+  private lastKilocodeTokenCheckAt = 0;
+  private async refreshKilocodeTokenIfExpiring(): Promise<void> {
+    const CHECK_INTERVAL_MS = 24 * 60 * 60_000; // once per day
+    const REFRESH_WINDOW_SECONDS = 7 * 24 * 60 * 60; // 7 days
+    const now = Date.now();
+    if (now - this.lastKilocodeTokenCheckAt < CHECK_INTERVAL_MS) return;
+    this.lastKilocodeTokenCheckAt = now;
+
+    const townConfig = await this.getTownConfig();
+    const token = townConfig.kilocode_token;
+    if (!token) return;
+
+    // Decode JWT payload (base64url, no verification)
+    const parts = token.split('.');
+    const encodedPayload = parts[1];
+    if (!encodedPayload) return;
+    const payloadSchema = z.object({
+      exp: z.number().optional(),
+      kiloUserId: z.string().optional(),
+      apiTokenPepper: z.string().nullable().optional(),
+    });
+    let rawPayload: unknown;
+    try {
+      rawPayload = JSON.parse(atob(encodedPayload.replace(/-/g, '+').replace(/_/g, '/')));
+    } catch {
+      return;
+    }
+    const parsed = payloadSchema.safeParse(rawPayload);
+    if (!parsed.success) return;
+    const payload = parsed.data;
+
+    const exp = payload.exp;
+    if (!exp) return;
+
+    const nowSeconds = Math.floor(now / 1000);
+    if (exp - nowSeconds > REFRESH_WINDOW_SECONDS) return;
+
+    // Token expires within 7 days — remint it
+    const userId = payload.kiloUserId;
+    if (!userId) return;
+
+    if (!this.env.NEXTAUTH_SECRET) {
+      logger.warn('refreshKilocodeTokenIfExpiring: NEXTAUTH_SECRET not configured');
+      return;
+    }
+    const secret = await resolveSecret(this.env.NEXTAUTH_SECRET);
+    if (!secret) {
+      logger.warn('refreshKilocodeTokenIfExpiring: failed to resolve NEXTAUTH_SECRET');
+      return;
+    }
+
+    const newToken = await generateKiloApiToken(
+      { id: userId, api_token_pepper: payload.apiTokenPepper ?? null },
+      secret
+    );
+    await this.updateTownConfig({ kilocode_token: newToken });
+    await this.syncConfigToContainer();
+    logger.info('refreshKilocodeTokenIfExpiring: reminted KILOCODE_TOKEN proactively', {
+      userId,
+      oldExp: new Date(exp * 1000).toISOString(),
+    });
+  }
+
   private hasActiveWork(): boolean {
     return scheduling.hasActiveWork(this.sql);
   }
diff --git a/cloudflare-gastown/src/trpc/router.ts b/cloudflare-gastown/src/trpc/router.ts
index 8169c0d7c..c1551d2d7 100644
--- a/cloudflare-gastown/src/trpc/router.ts
+++ b/cloudflare-gastown/src/trpc/router.ts
@@ -1018,6 +1018,13 @@ export const gastownRouter = router({
       }
       const townStub = getTownDOStub(ctx.env, input.townId);
       await townStub.forceRefreshContainerToken();
+
+      // Also remint and push KILOCODE_TOKEN — this is what actually
+      // authenticates GT tool calls and is the main reason users hit 401s.
+      const user = userFromCtx(ctx);
+      const newKilocodeToken = await mintKilocodeToken(ctx.env, user);
+      await townStub.updateTownConfig({ kilocode_token: newKilocodeToken });
+      await townStub.syncConfigToContainer();
     }),
 
   // ── Events ──────────────────────────────────────────────────────────