diff --git a/packages/core/src/session/compaction.ts b/packages/core/src/session/compaction.ts
index 5229949cb958..147af89b6bc4 100644
--- a/packages/core/src/session/compaction.ts
+++ b/packages/core/src/session/compaction.ts
@@ -130,7 +130,7 @@ const settings = (documents: readonly Config.Entry[]) => {
   )
 }
 
-const select = (
+export const select = (
   entries: readonly Entry[],
   tokens: number,
 ): { readonly head: string; readonly recent: string } | undefined => {
@@ -140,7 +140,12 @@ const select = (
     .filter(Boolean)
   if (conversation.length === 0) return
   let total = 0
-  let split = conversation.length
+  // head ends at headEnd (exclusive); recent starts at recentStart. They differ
+  // only when the budget boundary lands mid-message: that message is split into
+  // splitPrefix (head) and splitSuffix (recent), so the full message must NOT
+  // also appear in head's slice — head ends at `index`, recent starts at `index + 1`.
+  let headEnd = conversation.length
+  let recentStart = conversation.length
   let splitPrefix = ""
   let splitSuffix = ""
   for (let index = conversation.length - 1; index >= 0; index--) {
@@ -150,16 +155,22 @@ const select = (
       if (remaining > 0) {
         splitPrefix = conversation[index].slice(0, -remaining)
         splitSuffix = conversation[index].slice(-remaining)
-        split = index + 1
+        headEnd = index
+        recentStart = index + 1
+      } else {
+        // No room even for a suffix: the boundary message goes entirely to head.
+        headEnd = index + 1
+        recentStart = index + 1
       }
       break
     }
     total = next
-    split = index
+    headEnd = index
+    recentStart = index
   }
   return {
-    head: [...conversation.slice(0, split), splitPrefix].filter(Boolean).join("\n\n"),
-    recent: [splitSuffix, ...conversation.slice(split)].filter(Boolean).join("\n\n"),
+    head: [...conversation.slice(0, headEnd), splitPrefix].filter(Boolean).join("\n\n"),
+    recent: [splitSuffix, ...conversation.slice(recentStart)].filter(Boolean).join("\n\n"),
   }
 }
 
diff --git a/packages/core/test/session-compaction.test.ts b/packages/core/test/session-compaction.test.ts
index e91c89c00954..b0bfcaa85793 100644
--- a/packages/core/test/session-compaction.test.ts
+++ b/packages/core/test/session-compaction.test.ts
@@ -1,5 +1,7 @@
 import { expect, test } from "bun:test"
+import { DateTime } from "effect"
 import { SessionCompaction } from "@opencode-ai/core/session/compaction"
+import { SessionMessage } from "@opencode-ai/core/session/message"
 
 test("compaction describes tool media without embedding base64", () => {
   const base64 = "iVBORw0KGgoAAAANSUhEUgAAAAEAAAAB"
@@ -16,3 +18,44 @@ test("compaction describes tool media without embedding base64", () => {
   expect(serialized).toBe("Image read successfully\n[Attached image/png: pixel.png]")
   expect(serialized).not.toContain(base64)
 })
+
+const created = DateTime.makeUnsafe(0)
+const userEntry = (seq: number, text: string) => ({
+  seq,
+  message: new SessionMessage.User({
+    id: SessionMessage.ID.make(`msg_${seq}`),
+    type: "user",
+    text,
+    time: { created },
+  }),
+})
+
+test("select does not duplicate the boundary message into head", () => {
+  // serialize() renders a user message as `[User]: <text>`; Token.estimate is
+  // round(length / 4). With tokens=5: the small message (estimate 3) fits, then
+  // the big message overflows and is split mid-message. The boundary message
+  // must appear in head ONLY as the truncated prefix — never in full.
+  const big = "A".repeat(40)
+  const entries = [userEntry(0, big), userEntry(1, "BBBB")]
+
+  const result = SessionCompaction.select(entries, 5)
+
+  expect(result).toBeDefined()
+  // head is just the prefix slice, not the full boundary message + its prefix.
+  expect(result!.head).toBe(`[User]: ${"A".repeat(32)}`)
+  expect(result!.recent).toBe(`${"A".repeat(8)}\n\n[User]: BBBB`)
+  // Regression guard for the duplication bug (head once contained the full
+  // 40-char message AND its 32-char prefix copy):
+  expect(result!.head).not.toContain("A".repeat(40))
+  expect(result!.head.split("[User]:").length - 1).toBe(1)
+})
+
+test("select keeps everything in recent when the whole conversation fits", () => {
+  const entries = [userEntry(0, "first"), userEntry(1, "second")]
+
+  const result = SessionCompaction.select(entries, 1000)
+
+  expect(result).toBeDefined()
+  expect(result!.head).toBe("")
+  expect(result!.recent).toBe("[User]: first\n\n[User]: second")
+})