diff --git a/CHANGELOG.md b/CHANGELOG.md
index bd611f32f44..4c54ca26ff2 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -69,6 +69,7 @@ Docs: https://docs.openclaw.ai
 - TUI/History: cap chat-log component growth and prune stale render nodes/references so large default history loads no longer overflow render recursion with `RangeError: Maximum call stack size exceeded`. (#18068) Thanks @JaniJegoroff.
 - Memory/QMD: diversify mixed-source search ranking when both session and memory collections are present so session transcript hits no longer crowd out durable memory-file matches in top results. (#19913) Thanks @alextempr.
 - Memory/Tools: return explicit `unavailable` warnings/actions from `memory_search` when embedding/provider failures occur (including quota exhaustion), so disabled memory does not look like an empty recall result. (#21894) Thanks @XBS9.
+- Session/Startup: require the `/new` and `/reset` greeting path to run Session Startup file-reading instructions before responding, so daily memory startup context is not skipped on fresh-session greetings. (#22338) Thanks @armstrong-pv.
 - Auth/Onboarding: align OAuth profile-id config mapping with stored credential IDs for OpenAI Codex and Chutes flows, preventing `provider:default` mismatches when OAuth returns email-scoped credentials. (#12692) thanks @mudrii.
 - Docker: pin base images to SHA256 digests in Docker builds to prevent mutable tag drift. (#7734) Thanks @coygeek.
 - Docker/Security: run E2E and install-sh test images as non-root by adding appuser directives. Thanks @thewilloftheshadow.
diff --git a/src/auto-reply/reply.triggers.trigger-handling.test-harness.ts b/src/auto-reply/reply.triggers.trigger-handling.test-harness.ts
index f891acb51f6..e5113d2300d 100644
--- a/src/auto-reply/reply.triggers.trigger-handling.test-harness.ts
+++ b/src/auto-reply/reply.triggers.trigger-handling.test-harness.ts
@@ -229,6 +229,7 @@ export async function runGreetingPromptForBareNewOrReset(params: {
   expect(getRunEmbeddedPiAgentMock()).toHaveBeenCalledOnce();
   const prompt = getRunEmbeddedPiAgentMock().mock.calls[0]?.[0]?.prompt ?? "";
   expect(prompt).toContain("A new session was started via /new or /reset");
+  expect(prompt).toContain("Execute your Session Startup sequence now");
 }
 
 export function installTriggerHandlingE2eTestHooks() {
diff --git a/src/auto-reply/reply/session-reset-prompt.ts b/src/auto-reply/reply/session-reset-prompt.ts
index 0c16f15c11e..6a98cd42633 100644
--- a/src/auto-reply/reply/session-reset-prompt.ts
+++ b/src/auto-reply/reply/session-reset-prompt.ts
@@ -1,2 +1,2 @@
 export const BARE_SESSION_RESET_PROMPT =
-  "A new session was started via /new or /reset. Greet the user in your configured persona, if one is provided. Be yourself - use your defined voice, mannerisms, and mood. Keep it to 1-3 sentences and ask what they want to do. If the runtime model differs from default_model in the system prompt, mention the default model. Do not mention internal steps, files, tools, or reasoning.";
+  "A new session was started via /new or /reset. Execute your Session Startup sequence now - read the required files before responding to the user. Then greet the user in your configured persona, if one is provided. Be yourself - use your defined voice, mannerisms, and mood. Keep it to 1-3 sentences and ask what they want to do. If the runtime model differs from default_model in the system prompt, mention the default model. Do not mention internal steps, files, tools, or reasoning.";
diff --git a/src/gateway/server-methods/agent.test.ts b/src/gateway/server-methods/agent.test.ts
index eead292da04..26200057863 100644
--- a/src/gateway/server-methods/agent.test.ts
+++ b/src/gateway/server-methods/agent.test.ts
@@ -342,6 +342,7 @@ describe("gateway agent handler", () => {
       | { message?: string; sessionId?: string }
       | undefined;
     expect(call?.message).toBe(BARE_SESSION_RESET_PROMPT);
+    expect(call?.message).toContain("Execute your Session Startup sequence now");
     expect(call?.sessionId).toBe("reset-session-id");
   });
 
diff --git a/src/gateway/server.agent.gateway-server-agent-b.e2e.test.ts b/src/gateway/server.agent.gateway-server-agent-b.e2e.test.ts
index ae16d9cc6aa..fe786188574 100644
--- a/src/gateway/server.agent.gateway-server-agent-b.e2e.test.ts
+++ b/src/gateway/server.agent.gateway-server-agent-b.e2e.test.ts
@@ -285,6 +285,8 @@ describe("gateway server agent", () => {
     await vi.waitFor(() => expect(calls.length).toBeGreaterThan(callsBefore));
     const call = (calls.at(-1)?.[0] ?? {}) as Record<string, unknown>;
     expect(call.message).toBe(BARE_SESSION_RESET_PROMPT);
+    expect(call.message).toBeTypeOf("string");
+    expect(call.message).toContain("Execute your Session Startup sequence now");
     expect(typeof call.sessionId).toBe("string");
     expect(call.sessionId).not.toBe("sess-main-before-reset");
   });