diff --git a/CHANGELOG.md b/CHANGELOG.md
index ca22584..3c966aa 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -16,6 +16,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 - **CUA mode** (`configure({ ai: { mode: "cua" } })`): execute `runSteps` and `runUserFlow` through OpenAI's Responses API with the built-in `computer` tool. Screenshot-driven, coordinate-based actions via Playwright's `page.mouse` / `page.keyboard`. Requires `OPENAI_API_KEY` and `gateway: "none"`; Redis step caching is skipped in this mode because coordinate actions aren't portable across viewport sizes.
 - `cua` model slot in `ModelConfig` (default: `gpt-5.5`). For now, you cannot override the CUA model.
 - `getMode()` helper and `AIMode` type exported from `src/config.ts`.
+- **File upload caching**: `browser_upload_file` now writes a step cache entry, so repeat runs replay the cached upload-button locator instead of re-resolving it through the model. The flow is unchanged — the file chooser is still opened by clicking the button and the files are still set with `fileChooser.setFiles`.
 
 ## [1.0.0] - 2026-03-27
 
diff --git a/src/__tests__/upload-file.test.ts b/src/__tests__/upload-file.test.ts
index 9382bb5..d693306 100644
--- a/src/__tests__/upload-file.test.ts
+++ b/src/__tests__/upload-file.test.ts
@@ -1,5 +1,5 @@
 import { describe, expect, it } from "vitest";
-import { resolveUploadPath } from "../tools";
+import { resolveCachedUploadPaths, resolveUploadPath } from "../tools";
 
 describe("resolveUploadPath", () => {
   it("returns absolute Unix paths as-is", () => {
@@ -33,3 +33,35 @@ describe("resolveUploadPath", () => {
     expect(resolveUploadPath("uploads/test/document.pdf", "./uploads")).toBe("./uploads/uploads/test/document.pdf");
   });
 });
+
+describe("cached upload path resolution", () => {
+  it("resolves a raw filename coming from step.data", () => {
+    expect(resolveCachedUploadPaths("report.pdf", "", "./uploads")).toEqual([
+      "./uploads/report.pdf",
+    ]);
+  });
+
+  it("does not re-prefix the cached value when step.data has no value", () => {
+    expect(resolveCachedUploadPaths(undefined, "./uploads/a.pdf,/tmp/b.png", "./uploads")).toEqual([
+      "./uploads/a.pdf",
+      "/tmp/b.png",
+    ]);
+  });
+
+  it("prefers step.data over the cached value", () => {
+    expect(resolveCachedUploadPaths("fresh.pdf", "./uploads/stale.pdf", "./uploads")).toEqual([
+      "./uploads/fresh.pdf",
+    ]);
+  });
+
+  it("splits multiple raw filenames and skips empty entries", () => {
+    expect(resolveCachedUploadPaths("a.pdf, b.png,", "", "./uploads")).toEqual([
+      "./uploads/a.pdf",
+      "./uploads/b.png",
+    ]);
+  });
+
+  it("returns an empty list when neither source has a value", () => {
+    expect(resolveCachedUploadPaths(undefined, undefined, "./uploads")).toEqual([]);
+  });
+});
diff --git a/src/index.ts b/src/index.ts
index 75ee9d4..40b0e65 100644
--- a/src/index.ts
+++ b/src/index.ts
@@ -22,7 +22,7 @@ async function maybeWithSpan<T>(
 import { z } from "zod";
 import { buildRunStepsPrompt, buildRunUserFlowPrompt } from "./prompts";
 import { getRedis } from "./redis";
-import { getAItools } from "./tools";
+import { getAItools, resolveCachedUploadPaths } from "./tools";
 import { RunStepsOptions, UserFlowOptions } from "./types";
 import {
   runLocatorCode,
@@ -40,7 +40,7 @@ import {
   replacePlaceholders,
   resolveEmailPlaceholders,
 } from "./data-cache";
-import { resolveAI } from "./config";
+import { getConfig, resolveAI } from "./config";
 import { runCUALoop, buildRunStepsPromptCUA, buildRunUserFlowPromptCUA } from "./cua";
 import { applyExtraction } from "./extract";
 import { logger } from "./logger";
@@ -385,6 +385,22 @@ export const runSteps = async ({
         case "select-option":
           code = `await page.${locator}.describe('${description}').selectOption("${input}", { timeout: ${CACHED_ACTION_TIMEOUT} })`;
           break;
+        case "uploadFile": {
+          // `input` is deliberately not used here: see resolveCachedUploadPaths.
+          const uploadPaths = resolveCachedUploadPaths(
+            step.data?.value,
+            value,
+            getConfig().uploadBasePath || "./uploads",
+          );
+
+          code = `
+            const fileChooserPromise = page.waitForEvent('filechooser');
+            await page.${locator}.describe('${description}').click({ timeout: ${CACHED_ACTION_TIMEOUT} });
+            const fileChooser = await fileChooserPromise;
+            await fileChooser.setFiles(${JSON.stringify(uploadPaths)});
+          `;
+          break;
+        }
         case "waitForText":
           code = `await page.getByText("${value}", { exact: true }).first().waitFor({ state: "visible" })`;
           break;
diff --git a/src/tools.ts b/src/tools.ts
index e02f8b3..e3d3016 100644
--- a/src/tools.ts
+++ b/src/tools.ts
@@ -22,6 +22,27 @@ export function resolveUploadPath(filePath: string, uploadBasePath: string): str
     : `${uploadBasePath}/${filePath}`;
 }
 
+/**
+ * Resolves the file paths a cached "uploadFile" step should attach. The two sources hold
+ * different things: `rawValue` (from the step's data) is an unresolved filename, while
+ * `cachedValue` was already resolved against the base path when the step was recorded and
+ * must be used as-is — resolving it again would re-prefix it whenever `uploadBasePath` is
+ * relative, which is the default.
+ */
+export function resolveCachedUploadPaths(
+  rawValue: string | undefined,
+  cachedValue: string | undefined,
+  uploadBasePath: string,
+): string[] {
+  return (rawValue ?? cachedValue ?? "")
+    .split(",")
+    .map((filePath) => filePath.trim())
+    .filter(Boolean)
+    .map((filePath) =>
+      rawValue === undefined ? filePath : resolveUploadPath(filePath, uploadBasePath),
+    );
+}
+
 type ToolSettings = {
   abortController?: AbortController;
   currentStep?: { description: string; data?: Record<string, string> };
@@ -588,8 +609,12 @@ class PlaywrightTools {
     const uploadBasePath = getConfig().uploadBasePath || "./uploads";
     const prefixedFilePaths = filePaths.map((filePath) => resolveUploadPath(filePath, uploadBasePath));
 
-    // File uploads are not cached for now as it needs a two step process
-    // We can solve this later by introducing multi-action caching if needed
+    let cachedLocator = "";
+
+    if (this.currentStep) {
+      cachedLocator = await this.resolveLocator(locator);
+    }
+
     const fileChooserPromise = this.page.waitForEvent("filechooser");
     await locator.click({ timeout: LOCATOR_ACTION_TIMEOUT });
     const fileChooser = await fileChooserPromise;
@@ -597,6 +622,15 @@ class PlaywrightTools {
       timeout: LOCATOR_ACTION_TIMEOUT,
     });
 
+    // Cached as a single "uploadFile" action: the locator stored is the button that opens
+    // the file chooser, and the replay in index.ts performs both steps against it.
+    this.prepareCacheData(
+      cachedLocator,
+      "uploadFile",
+      elementDescription,
+      prefixedFilePaths.join(","),
+    );
+
     return {
       success: true,
       prefixedFilePaths,