diff --git a/packages/opencode/src/session/compaction.ts b/packages/opencode/src/session/compaction.ts
index 75d6374bfa54..3f1e2a0b9973 100644
--- a/packages/opencode/src/session/compaction.ts
+++ b/packages/opencode/src/session/compaction.ts
@@ -31,6 +31,9 @@ const TOOL_OUTPUT_MAX_CHARS = 2_000
 const PRUNE_PROTECTED_TOOLS = ["skill"]
 const MIN_PRESERVE_RECENT_TOKENS = 2_000
 const MAX_PRESERVE_RECENT_TOKENS = 15_000
+// Prompt template, previous summary, and plugin context that accompany the
+// serialized head in the summarizer request.
+const SUMMARIZER_PROMPT_RESERVE = 8_000
 type Turn = {
   start: number
   end: number
@@ -162,6 +165,40 @@ function splitTurn(input: {
   })
 }
 
+// The summarizer request only carries the serialized head. When it no longer
+// fits the model's usable context, drop the oldest complete turns instead of
+// giving up with "session too large to compact".
+function shrinkHeadToBudget(input: {
+  messages: SessionV1.WithParts[]
+  model: Provider.Model
+  budget: number
+  estimate: (input: { messages: SessionV1.WithParts[]; model: Provider.Model }) => Effect.Effect<number>
+}) {
+  return Effect.gen(function* () {
+    let total = yield* input.estimate({ messages: input.messages, model: input.model })
+    if (total <= input.budget) return input.messages
+    const all = turns(input.messages)
+    let start = 0
+    let i = 0
+    while (total > input.budget && i < all.length - 1) {
+      const next = all[i + 1]
+      total -= yield* input.estimate({
+        messages: input.messages.slice(start, next.start),
+        model: input.model,
+      })
+      start = next.start
+      i++
+    }
+    if (start === 0) return input.messages
+    yield* Effect.logInfo("head exceeds budget; dropping oldest turns", {
+      dropped: start,
+      kept: input.messages.length - start,
+      budget: input.budget,
+    })
+    return input.messages.slice(start)
+  })
+}
+
 export interface Interface {
   readonly isOverflow: (input: {
     tokens: SessionV1.Assistant["tokens"]
@@ -375,7 +412,13 @@ const layer = Layer.effect(
         { sessionID: input.sessionID },
         { context: [], prompt: undefined },
       )
-      const msgs = structuredClone(selected.head)
+      const head = yield* shrinkHeadToBudget({
+        messages: selected.head,
+        model,
+        budget: Math.max(0, usable({ cfg, model, outputTokenMax: flags.outputTokenMax }) - SUMMARIZER_PROMPT_RESERVE),
+        estimate,
+      })
+      const msgs = structuredClone(head)
       yield* plugin.trigger("experimental.chat.messages.transform", {}, { messages: msgs })
       const conversation = msgs.map(serialize).filter(Boolean).join("\n\n")
       const nextPrompt =
diff --git a/packages/opencode/test/session/compaction.test.ts b/packages/opencode/test/session/compaction.test.ts
index c76dd98b8614..03165e5219ef 100644
--- a/packages/opencode/test/session/compaction.test.ts
+++ b/packages/opencode/test/session/compaction.test.ts
@@ -1051,6 +1051,43 @@ describe("session.compaction.process", () => {
     { git: true },
   )
 
+  itCompaction.instance(
+    "drops oldest turns when the head exceeds the model context budget",
+    () => {
+      const stub = llm()
+      let captured = ""
+      stub.push(reply("summary", (input) => (captured = JSON.stringify(input.messages))))
+      return Effect.gen(function* () {
+        const ssn = yield* SessionNs.Service
+        const session = yield* ssn.create({})
+        yield* createUserMessage(session.id, "x".repeat(24_000))
+        yield* createUserMessage(session.id, "y".repeat(8_000))
+        yield* createSummaryCompaction(session.id)
+
+        const msgs = yield* ssn.messages({ sessionID: session.id })
+        const parent = msgs.at(-1)?.info.id
+        expect(parent).toBeTruthy()
+        const result = yield* SessionCompaction.use.process({
+          parentID: parent!,
+          messages: msgs,
+          sessionID: session.id,
+          auto: false,
+        })
+
+        expect(result).toBe("continue")
+        expect(captured).toContain("yyyy")
+        expect(captured).not.toContain("xxxx")
+      }).pipe(
+        withCompaction({
+          llm: stub.llmLayer,
+          provider: ProviderTest.fake({ model: createModel({ context: 20_000, output: 8_000 }) }),
+          config: cfg({ preserve_recent_tokens: 100 }),
+        }),
+      )
+    },
+    { git: true },
+  )
+
   itCompaction.instance(
     "retains a split turn suffix when a later message fits the preserve token budget",
     () => {