diff --git a/packages/core/src/session/compaction.ts b/packages/core/src/session/compaction.ts
index ba52eb77dd00..4b21ff348fe4 100644
--- a/packages/core/src/session/compaction.ts
+++ b/packages/core/src/session/compaction.ts
@@ -22,20 +22,27 @@ const SUMMARY_TEMPLATE = `Output exactly the Markdown structure shown inside <te
 - [constraints/preferences, decisions and why, important facts/assumptions, exact context needed to continue, or "(none)"]
 
 ## Work State
-- Completed: [finished work, verified facts, or changes made; otherwise "(none)"]
-- Active: [current work, partial changes, or investigation state; otherwise "(none)"]
-- Blocked: [blockers, failing commands, or unknowns; otherwise "(none)"]
+### Completed
+- [finished work, verified facts, or changes made; otherwise "(none)"]
+
+### Active
+- [current work, partial changes, or investigation state; otherwise "(none)"]
+
+### Blocked
+- [blockers, failing commands, or unknowns; otherwise "(none)"]
 
 ## Next Move
 1. [immediate concrete action, or "(none)"]
 2. [next action if known, or "(none)"]
+
+## Relevant Files
+- [file or directory path: why it matters, or "(none)"]
 </template>
 
 Rules:
 - Keep every section, even when empty.
 - Use terse bullets, not prose paragraphs.
 - Preserve exact file paths, symbols, commands, error strings, URLs, and identifiers when known.
-- Put relevant files and symbols inside the section where they matter; do not add extra sections.
 - Do not mention the summary process or that context was compacted.`
 
 type Entry = {
diff --git a/packages/core/test/session-compaction.test.ts b/packages/core/test/session-compaction.test.ts
index e91c89c00954..9d45e0acc334 100644
--- a/packages/core/test/session-compaction.test.ts
+++ b/packages/core/test/session-compaction.test.ts
@@ -1,6 +1,15 @@
 import { expect, test } from "bun:test"
 import { SessionCompaction } from "@opencode-ai/core/session/compaction"
 
+test("compaction prompt preserves detailed work state and relevant files", () => {
+  const prompt = SessionCompaction.buildPrompt({ context: ["conversation history"] })
+
+  expect(prompt).toContain("## Work State\n### Completed")
+  expect(prompt).toContain("### Active")
+  expect(prompt).toContain("### Blocked")
+  expect(prompt).toContain("## Relevant Files")
+})
+
 test("compaction describes tool media without embedding base64", () => {
   const base64 = "iVBORw0KGgoAAAANSUhEUgAAAAEAAAAB"
   const serialized = SessionCompaction.serializeToolContent([