diff --git a/packages/core/src/api/clipboard/fromClipboard/handleFileInsertion.test.ts b/packages/core/src/api/clipboard/fromClipboard/handleFileInsertion.test.ts
new file mode 100644
index 0000000000..1ef63daebe
--- /dev/null
+++ b/packages/core/src/api/clipboard/fromClipboard/handleFileInsertion.test.ts
@@ -0,0 +1,92 @@
+// @vitest-environment node
+import { describe, expect, it, vi } from "vite-plus/test";
+
+import { BlockNoteEditor } from "../../../editor/BlockNoteEditor.js";
+import { handleFileInsertion } from "./handleFileInsertion.js";
+
+describe("File insertion", () => {
+  it.each(["drop", "paste"] as const)(
+    "uploads and inserts all files in order after %s data becomes unavailable",
+    async (eventType) => {
+      let finishUpload!: () => void;
+      const uploadPending = new Promise<void>((resolve) => {
+        finishUpload = resolve;
+      });
+      const uploadFile = vi.fn(async (file: File) => {
+        await uploadPending;
+        return `https://example.com/${file.name}`;
+      });
+      const editor = BlockNoteEditor.create({
+        initialContent: [{ type: "paragraph" }],
+        trailingBlock: false,
+        uploadFile,
+      });
+
+      try {
+        // Resolve drops to the first block without mounting a view.
+        Object.defineProperty(editor, "prosemirrorView", {
+          value: {
+            posAtCoords: () => ({ pos: 1, inside: -1 }),
+          } satisfies Pick<BlockNoteEditor["prosemirrorView"], "posAtCoords">,
+        });
+        const files = [
+          new File(["first"], "first.png", { type: "image/png" }),
+          new File(["second"], "second.pdf", { type: "application/pdf" }),
+        ];
+        let protectedData = false;
+        const items = files.map((file) => ({
+          kind: "file",
+          type: file.type,
+          getAsFile: () => (protectedData ? null : file),
+        }));
+        const event =
+          eventType === "drop"
+            ? new DragEvent("drop", { cancelable: true })
+            : new ClipboardEvent("paste", { cancelable: true });
+        Object.defineProperty(
+          event,
+          eventType === "drop" ? "dataTransfer" : "clipboardData",
+          { value: { types: ["Files"], items } },
+        );
+        const target = new EventTarget();
+        let insertion = Promise.resolve();
+        target.addEventListener(eventType, () => {
+          insertion = handleFileInsertion(event, editor);
+        });
+        target.dispatchEvent(event);
+        // Native event data is only available during synchronous dispatch.
+        protectedData = true;
+        items.length = 0;
+        expect(uploadFile).toHaveBeenCalledTimes(1);
+        finishUpload();
+        await insertion;
+
+        expect.soft(uploadFile).toHaveBeenCalledTimes(2);
+        expect(
+          editor.document.map((block) => ({
+            type: block.type,
+            props: block.props,
+          })),
+        ).toMatchObject([
+          {
+            type: "image",
+            props: {
+              name: "first.png",
+              url: "https://example.com/first.png",
+            },
+          },
+          {
+            type: "file",
+            props: {
+              name: "second.pdf",
+              url: "https://example.com/second.pdf",
+            },
+          },
+        ]);
+        expect(uploadFile.mock.calls.map(([file]) => file)).toEqual(files);
+      } finally {
+        editor._tiptapEditor.destroy();
+      }
+    },
+  );
+});
diff --git a/packages/core/src/api/clipboard/fromClipboard/handleFileInsertion.ts b/packages/core/src/api/clipboard/fromClipboard/handleFileInsertion.ts
index 9561927f0f..fcce065021 100644
--- a/packages/core/src/api/clipboard/fromClipboard/handleFileInsertion.ts
+++ b/packages/core/src/api/clipboard/fromClipboard/handleFileInsertion.ts
@@ -105,20 +105,24 @@ export async function handleFileInsertion<
 
   event.preventDefault();
 
-  for (let i = 0; i < items.length; i++) {
+  // Capture files before awaiting uploads, while event data is still available.
+  const files = Array.from(items, (item) => ({
+    file: item.getAsFile(),
+    type: item.type,
+  }));
+
+  for (const { file, type } of files) {
     // Gets file block corresponding to MIME type.
     let fileBlockType = "file";
     for (const blockSpec of Object.values(editor.schema.blockSpecs)) {
       for (const mimeType of blockSpec.implementation.meta.fileBlockAccept ||
         []) {
         const isFileExtension = mimeType.startsWith(".");
-        const file = items[i].getAsFile();
-
         if (file) {
           if (
             (!isFileExtension &&
               file.type &&
-              checkMIMETypesMatch(items[i].type, mimeType)) ||
+              checkMIMETypesMatch(type, mimeType)) ||
             (isFileExtension &&
               checkFileExtensionsMatch(
                 "." + file.name.split(".").pop(),
@@ -132,7 +136,6 @@ export async function handleFileInsertion<
       }
     }
 
-    const file = items[i].getAsFile();
     if (file) {
       const fileBlock = {
         type: fileBlockType,