From bca309457b875288a607a32fd01ce88e5b61ada4 Mon Sep 17 00:00:00 2001
From: Prudhvi Vuda <53619858+Prudhvivuda@users.noreply.github.com>
Date: Mon, 27 Jul 2026 18:07:37 -0400
Subject: [PATCH] feat(providers): flatten multi-turn history for gemini-web
 (#8371) (#8607)
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gemini-web is a stateless Web Cookie provider: it drives a real browser
page and captures only the first StreamGenerate response, so it has no
upstream conversation id to thread across turns. The no-tools path
forwarded only the last user message
(`messages.filter(m => m.role === "user").pop()`), so follow-up questions
lost all prior context — e.g. "I am in Berlin" then "What should I wear
today?" was answered without Berlin.

Implement the issue's accepted fallback (b): flatten the full messages
history into the single prompt typed into the web UI, emitting a labeled
System / Previous conversation / Current user message transcript.
Single-turn requests are preserved byte-for-byte (only the final user
message is returned), keeping the #7286 no-tools regression guard intact.
Applies uniformly to streaming and non-streaming since both derive from
the same `prompt`.

claude-web already threads context via its conversation cache
(session.ts, #8230) and needs no change.

Closes #8371
---
 open-sse/executors/gemini-web.ts              | 73 +++++++++++++++++-
 .../gemini-web-multiturn-context-8371.test.ts | 75 +++++++++++++++++++
 2 files changed, 145 insertions(+), 3 deletions(-)
 create mode 100644 tests/unit/gemini-web-multiturn-context-8371.test.ts

diff --git a/open-sse/executors/gemini-web.ts b/open-sse/executors/gemini-web.ts
index de018e77b0..4befb78c6e 100644
--- a/open-sse/executors/gemini-web.ts
+++ b/open-sse/executors/gemini-web.ts
@@ -73,6 +73,70 @@ function formatStreamChunk(content: string, model: string, finishReason: string
   };
 }
 
+/**
+ * Flatten the OpenAI-style multi-turn `messages[]` into the single plain-text
+ * prompt typed into the Gemini web UI (#8371).
+ *
+ * gemini-web drives a real browser page and captures only the FIRST
+ * `StreamGenerate` response, so — unlike claude-web — it has no upstream
+ * conversation id to thread across turns. It is therefore a stateless,
+ * single-turn provider: the previous code forwarded only the last user message
+ * (`messages.filter(m => m.role === "user").pop()`), so follow-up questions
+ * lost all prior context ("I am in Berlin" → "What should I wear today?" was
+ * answered without Berlin). This implements the issue's accepted fallback (b):
+ * flatten the full history into one prompt so the web UI still sees the
+ * conversation.
+ *
+ * Single-turn requests are preserved byte-for-byte (only the final user message
+ * is returned) — the regression guard for the pre-existing no-tools path.
+ * Multi-turn requests emit a labeled transcript:
+ *
+ *   System:
+ *   <system text>
+ *
+ *   Previous conversation:
+ *   User: ...
+ *   Assistant: ...
+ *
+ *   Current user message:
+ *   <last user message>
+ */
+export function buildGeminiPrompt(messages: Array<{ role: string; content: unknown }>): string {
+  const textMessages = messages.filter(
+    (m) => typeof m.content === "string" && (m.content as string).trim().length > 0
+  ) as Array<{ role: string; content: string }>;
+
+  const userMessages = textMessages.filter((m) => m.role === "user");
+  const lastUser = userMessages[userMessages.length - 1];
+  const lastUserContent = lastUser?.content ?? "";
+  const lastUserIdx = lastUser ? textMessages.lastIndexOf(lastUser) : -1;
+
+  // Prior conversation = every user/assistant turn before the final user turn.
+  const priorTurns = textMessages.filter(
+    (m, i) => i < lastUserIdx && (m.role === "user" || m.role === "assistant")
+  );
+
+  // Single-turn (no earlier user/assistant turns): byte-for-byte the original
+  // single-message derivation. Do NOT prepend system text here — the old
+  // no-tools path ignored a system-only prefix on the first turn.
+  if (priorTurns.length === 0) return lastUserContent;
+
+  const systemText = textMessages
+    .filter((m) => m.role === "system")
+    .map((m) => m.content)
+    .join("\n\n");
+
+  const historyLines = priorTurns.map(
+    (m) => `${m.role === "assistant" ? "Assistant" : "User"}: ${m.content}`
+  );
+
+  const parts: string[] = [];
+  if (systemText) parts.push(`System:\n${systemText}`);
+  parts.push(`Previous conversation:\n${historyLines.join("\n\n")}`);
+  parts.push(`Current user message:\n${lastUserContent}`);
+  return parts.join("\n\n");
+}
+
 /**
  * Build the plain-text prompt typed into the Gemini web UI when a tool
  * contract is active — the synthetic system message injected by
@@ -337,11 +401,14 @@ export class GeminiWebExecutor extends BaseExecutor {
       messages
     );
 
-    // hasTools === false: byte-for-byte the original prompt derivation
-    // (regression guard — #7286 must not touch the no-tools path).
+    // hasTools === false: flatten the full multi-turn history into the single
+    // prompt so gemini-web (a stateless web-cookie provider that captures only
+    // the first StreamGenerate response) preserves prior context across turns
+    // (#8371). Single-turn requests stay byte-for-byte identical to the original
+    // derivation, keeping the #7286 no-tools regression guard intact.
     const prompt = hasTools
       ? buildGeminiToolPrompt(effectiveMessages)
-      : messages.filter((m) => m.role === "user").pop()?.content || "";
+      : buildGeminiPrompt(messages);
 
     if (!prompt) {
       return {
diff --git a/tests/unit/gemini-web-multiturn-context-8371.test.ts b/tests/unit/gemini-web-multiturn-context-8371.test.ts
new file mode 100644
index 0000000000..fca4965b9b
--- /dev/null
+++ b/tests/unit/gemini-web-multiturn-context-8371.test.ts
@@ -0,0 +1,75 @@
+import test from "node:test";
+import assert from "node:assert/strict";
+
+// #8371 — gemini-web is a stateless, single-turn Web Cookie provider: the
+// no-tools path historically forwarded only the LAST user message
+// (`messages.filter(m => m.role === "user").pop()`), dropping all prior turns
+// so follow-up questions lost context ("I am in Berlin" → "What should I wear?"
+// answered without Berlin). The issue's accepted fallback (b) is to flatten the
+// full messages history into the single prompt sent to the web UI. These tests
+// pin that flatten behavior while guaranteeing single-turn requests stay
+// byte-for-byte identical (regression guard for the existing no-tools path).
+
+const { buildGeminiPrompt } = await import("../../open-sse/executors/gemini-web.ts");
+
+// ─── Single-turn: byte-for-byte identical to the original derivation ─────────
+
+test("#8371: single user message returns that message verbatim (single-turn unchanged)", () => {
+  const prompt = buildGeminiPrompt([{ role: "user", content: "What about Paris?" }]);
+  assert.equal(prompt, "What about Paris?");
+});
+
+test("#8371: single user turn with a system message still returns only the user text", () => {
+  // Preserves the pre-existing no-tools derivation, which ignored system-only
+  // context on the first turn.
+  const prompt = buildGeminiPrompt([
+    { role: "system", content: "You are helpful" },
+    { role: "user", content: "Hello" },
+  ]);
+  assert.equal(prompt, "Hello");
+});
+
+// ─── Multi-turn: full history is flattened into the prompt ───────────────────
+
+test("#8371: multi-turn history is flattened so prior turns are preserved as context", () => {
+  const prompt = buildGeminiPrompt([
+    { role: "user", content: "I am in Berlin." },
+    { role: "assistant", content: "Nice, Berlin is great." },
+    { role: "user", content: "What should I wear today?" },
+  ]);
+
+  // The prior turns must survive into the prompt (this is what fails today —
+  // the old code only forwarded the final user message).
+  assert.match(prompt, /Berlin/);
+  assert.match(prompt, /I am in Berlin\./);
+  assert.match(prompt, /Nice, Berlin is great\./);
+  // The current question must still be present and clearly marked.
+  assert.match(prompt, /What should I wear today\?/);
+  // Prior turns are labeled by role.
+  assert.match(prompt, /User: I am in Berlin\./);
+  assert.match(prompt, /Assistant: Nice, Berlin is great\./);
+});
+
+test("#8371: system instructions are carried into the flattened multi-turn prompt", () => {
+  const prompt = buildGeminiPrompt([
+    { role: "system", content: "Always answer in French." },
+    { role: "user", content: "What about Paris?" },
+    { role: "assistant", content: "Paris is the capital of France." },
+    { role: "user", content: "How is the weather?" },
+  ]);
+  assert.match(prompt, /Always answer in French\./);
+  assert.match(prompt, /What about Paris\?/);
+  assert.match(prompt, /Paris is the capital of France\./);
+  assert.match(prompt, /How is the weather\?/);
+});
+
+test("#8371: non-string / empty message contents are ignored without throwing", () => {
+  const prompt = buildGeminiPrompt([
+    { role: "user", content: "First question" },
+    { role: "assistant", content: "" },
+    { role: "user", content: "Second question" },
+  ] as Array<{ role: string; content: string }>);
+  // Empty assistant turn drops out; the earlier user turn is still preserved.
+  assert.match(prompt, /First question/);
+  assert.match(prompt, /Second question/);
+});