diff --git a/apps/web/playwright/e2e/composer/CIDER.spec.ts b/apps/web/playwright/e2e/composer/CIDER.spec.ts
index d164a689e1..89f4cad276 100644
--- a/apps/web/playwright/e2e/composer/CIDER.spec.ts
+++ b/apps/web/playwright/e2e/composer/CIDER.spec.ts
@@ -8,6 +8,7 @@ Please see LICENSE files in the repository root for full details.
 
 import { test, expect } from "../../element-web-test";
 import { SettingLevel } from "../../../src/settings/SettingLevel";
+import { getSampleFilePath } from "../../sample-files";
 
 const CtrlOrMeta = process.platform === "darwin" ? "Meta" : "Control";
 
@@ -198,5 +199,16 @@ test.describe("Composer", () => {
             // Take a screenshot of the autocomplete
             await expect(autocomplete).toMatchScreenshot("emoji-autocomplete.png");
         });
+
+        test("can paste a file", async ({ page, bot, app }) => {
+            // Set up a private room so we have another user to mention
+            await app.client.createRoom({
+                is_direct: true,
+                invite: [bot.credentials.userId],
+            });
+            await app.viewRoomByName("Bob");
+            await app.composerDragAndPasteFile("room", getSampleFilePath("riot.png"), "image/png");
+            await expect(page.locator(".mx_MImageBody")).toBeVisible();
+        });
     });
 });
diff --git a/apps/web/playwright/e2e/composer/RTE.spec.ts b/apps/web/playwright/e2e/composer/RTE.spec.ts
index e88dd827fc..2c5f8071ec 100644
--- a/apps/web/playwright/e2e/composer/RTE.spec.ts
+++ b/apps/web/playwright/e2e/composer/RTE.spec.ts
@@ -8,6 +8,7 @@ Please see LICENSE files in the repository root for full details.
 
 import { test, expect } from "../../element-web-test";
 import { SettingLevel } from "../../../src/settings/SettingLevel";
+import { getSampleFilePath } from "../../sample-files";
 
 const CtrlOrMeta = process.platform === "darwin" ? "Meta" : "Control";
 
@@ -195,6 +196,26 @@ test.describe("Composer", () => {
             await expect(page.locator(".mx_EventTile_body strong").getByText("bold")).toBeVisible();
         });
 
+        test("can paste a file", async ({ page, bot, app }) => {
+            await app.composerDragAndPasteFile("room", getSampleFilePath("riot.png"), "image/png");
+            await expect(page.locator(".mx_MImageBody")).toBeVisible();
+        });
+
+        test("can paste a file in a thread", async ({ page, app }) => {
+            // Send a message
+            const composer = page.locator("div[contenteditable=true]");
+            await composer.pressSequentially("my first message");
+            await page.getByRole("button", { name: "Send message" }).click();
+
+            // Click reply
+            const tile = page.locator(".mx_EventTile_last");
+            await tile.hover();
+            await tile.getByRole("button", { name: "Reply in thread" }).click();
+
+            await app.composerDragAndPasteFile("thread", getSampleFilePath("riot.png"), "image/png");
+            await expect(page.locator(".mx_MImageBody")).toBeVisible();
+        });
+
         test.describe("when Control+Enter is required to send", () => {
             test.beforeEach(async ({ app }) => {
                 await app.settings.setValue("MessageComposerInput.ctrlEnterToSend", null, SettingLevel.ACCOUNT, true);
diff --git a/apps/web/playwright/e2e/threads/threads.spec.ts b/apps/web/playwright/e2e/threads/threads.spec.ts
index a454031933..c74ca570ea 100644
--- a/apps/web/playwright/e2e/threads/threads.spec.ts
+++ b/apps/web/playwright/e2e/threads/threads.spec.ts
@@ -405,6 +405,28 @@ test.describe("Threads", () => {
             await app.composerDragAndUploadFiles("thread", getSampleFilePath("riot.png"), "image/png");
             await expect(page.locator(".mx_ThreadView .mx_EventTile_image")).toHaveCount(1);
         });
+        test("can send files via paste", async ({ page, app, user }) => {
+            // Increase right-panel size, so that files fit
+            await page.evaluate(() => {
+                window.localStorage.setItem("mx_rhs_size", "600");
+            });
+
+            const roomId = await app.client.createRoom({});
+            await page.goto("/#/room/" + roomId);
+
+            // Send message
+            const locator = page.locator(".mx_RoomView_body");
+            await locator.getByRole("textbox", { name: "Send an unencrypted message…" }).fill("Hello Mr. Bot");
+            await locator.getByRole("textbox", { name: "Send an unencrypted message…" }).press("Enter");
+            // Create thread
+            const locator2 = locator.locator(".mx_EventTile[data-scroll-tokens]").filter({ hasText: "Hello Mr. Bot" });
+            await locator2.hover();
+            await locator2.getByRole("button", { name: "Reply in thread" }).click();
+
+            await expect(page.locator(".mx_ThreadView_timelinePanelWrapper")).toHaveCount(1);
+            await app.composerDragAndPasteFile("thread", getSampleFilePath("riot.png"), "image/png");
+            await expect(page.locator(".mx_ThreadView .mx_EventTile_image")).toHaveCount(1);
+        });
     });
 
     test(
diff --git a/apps/web/playwright/pages/ElementAppPage.ts b/apps/web/playwright/pages/ElementAppPage.ts
index ac9212fd10..41abc8f980 100644
--- a/apps/web/playwright/pages/ElementAppPage.ts
+++ b/apps/web/playwright/pages/ElementAppPage.ts
@@ -218,6 +218,40 @@ export class ElementAppPage {
         await this.page.locator(".mx_Dialog").getByRole("button", { name: "Upload" }).click();
     }
 
+    /**
+     * Paste a "file" into the specified locator and automatically uploads it.
+     * @param location Should the drop target the main room or the thread.
+     * @param path The path to the sample file so it can be read.
+     * @param type The mimetype of the file.
+     */
+    public async composerDragAndPasteFile(location: "room" | "thread", path: string, type: string): Promise<void> {
+        // Based on https://github.com/microsoft/playwright/issues/10667#issuecomment-2742123424
+        // This read a file, encodes it into base64 and then sends it along to the page to be treated
+        // as a DataTransfer (the mechanism for drag and dropped files).
+        const buffer = await readFile(path);
+        const name = basename(path);
+        const composer = this.getComposerField(location === "thread");
+
+        await composer.evaluate(
+            async (element, [buffer, name, type]) => {
+                const clipboardData = new DataTransfer();
+                const file = new File([Uint8Array.fromBase64(buffer)], name, {
+                    type,
+                });
+                clipboardData.items.add(file);
+                element.dispatchEvent(
+                    new ClipboardEvent("paste", {
+                        clipboardData,
+                        bubbles: true,
+                        cancelable: true,
+                    }),
+                );
+            },
+            [buffer.toString("base64"), name, type],
+        );
+        await this.page.locator(".mx_Dialog").getByRole("button", { name: "Upload" }).click();
+    }
+
     /**
      * Returns the space panel space button based on a name. The space
      * must be visible in the space panel