diff --git a/packages/core/src/api/clipboard/fromClipboard/handleFileInsertion.test.ts b/packages/core/src/api/clipboard/fromClipboard/handleFileInsertion.test.ts
index 1ef63daebe..c15bae66cb 100644
--- a/packages/core/src/api/clipboard/fromClipboard/handleFileInsertion.test.ts
+++ b/packages/core/src/api/clipboard/fromClipboard/handleFileInsertion.test.ts
@@ -5,6 +5,128 @@ import { BlockNoteEditor } from "../../../editor/BlockNoteEditor.js";
 import { handleFileInsertion } from "./handleFileInsertion.js";
 
 describe("File insertion", () => {
+  describe.each(["success", "rejection", "empty URL"] as const)(
+    "%s for the first upload",
+    (outcome) => {
+      it.each(["before", "after", "paste"] as const)(
+        "preserves transfer order (%s a nonempty paragraph)",
+        async (placement) => {
+          let finishFirstUpload!: () => void;
+          let finishSecondUpload!: () => void;
+          const firstPending = new Promise<void>((resolve) => {
+            finishFirstUpload = resolve;
+          });
+          const secondPending = new Promise<void>((resolve) => {
+            finishSecondUpload = resolve;
+          });
+          const uploadFile = vi.fn(async (file: File) => {
+            if (file.name === "image.gif") {
+              await firstPending;
+              if (outcome === "rejection") {
+                throw new Error("Upload rejected");
+              }
+              if (outcome === "empty URL") {
+                return "";
+              }
+            } else {
+              await secondPending;
+            }
+            return `https://example.com/${file.name}`;
+          });
+          const editor = BlockNoteEditor.create({
+            initialContent: [
+              { id: "target", type: "paragraph", content: "Wrapped paragraph" },
+            ],
+            trailingBlock: false,
+            uploadFile,
+          });
+
+          try {
+            editor.setTextCursorPosition("target", "end");
+            // Only layout is substituted: resolve the real target node after each
+            // insertion, as posAtCoords would for a drop over the paragraph.
+            Object.defineProperty(editor, "prosemirrorView", {
+              value: {
+                posAtCoords: () => {
+                  let targetPos = 0;
+                  editor.prosemirrorState.doc.descendants((node, pos) => {
+                    if (node.attrs.id === "target") {
+                      targetPos = pos + 1;
+                    }
+                  });
+                  return { pos: targetPos, inside: -1 };
+                },
+              } satisfies Pick<
+                BlockNoteEditor["prosemirrorView"],
+                "posAtCoords"
+              >,
+            });
+            Object.defineProperty(editor, "domElement", {
+              value: {
+                querySelector: () => ({
+                  getBoundingClientRect: () => ({ top: 0, bottom: 100 }),
+                }),
+              },
+            });
+            const files = [
+              new File(["first"], "image.gif", { type: "image/gif" }),
+              new File(["second"], "picture.png", { type: "image/png" }),
+            ];
+            const event =
+              placement === "paste"
+                ? new ClipboardEvent("paste", { cancelable: true })
+                : new DragEvent("drop", { cancelable: true });
+            Object.defineProperties(event, {
+              [placement === "paste" ? "clipboardData" : "dataTransfer"]: {
+                value: {
+                  types: ["Files"],
+                  items: files.map((file) => ({
+                    type: file.type,
+                    getAsFile: () => file,
+                  })),
+                },
+              },
+              clientX: { value: 10 },
+              clientY: { value: placement === "before" ? 10 : 90 },
+            });
+
+            const insertion = handleFileInsertion(event, editor);
+            // Uploads stay sequential. Let the first finish while the second is
+            // still pending, then check that its completion cannot reorder blocks.
+            expect(uploadFile).toHaveBeenCalledTimes(1);
+            finishFirstUpload();
+            await vi.waitFor(() => expect(uploadFile).toHaveBeenCalledTimes(2));
+
+            expect(event.defaultPrevented).toBe(true);
+            expect(uploadFile.mock.calls.map(([file]) => file)).toEqual(files);
+            const order = editor.document.map((block) =>
+              "name" in block.props ? block.props.name : block.id,
+            );
+            expect
+              .soft(order)
+              .toEqual(
+                placement === "before"
+                  ? ["image.gif", "picture.png", "target"]
+                  : ["target", "image.gif", "picture.png"],
+              );
+            finishSecondUpload();
+            await insertion;
+            expect(
+              editor.document
+                .filter((block) => block.type === "image")
+                .map((block) => block.props.url),
+            ).toEqual([
+              outcome === "success" ? "https://example.com/image.gif" : "",
+              "https://example.com/picture.png",
+            ]);
+          } finally {
+            editor._tiptapEditor.destroy();
+          }
+        },
+      );
+    },
+  );
+
   it.each(["drop", "paste"] as const)(
     "uploads and inserts all files in order after %s data becomes unavailable",
     async (eventType) => {
diff --git a/packages/core/src/api/clipboard/fromClipboard/handleFileInsertion.ts b/packages/core/src/api/clipboard/fromClipboard/handleFileInsertion.ts
index 31ac5cd104..7d911663c0 100644
--- a/packages/core/src/api/clipboard/fromClipboard/handleFileInsertion.ts
+++ b/packages/core/src/api/clipboard/fromClipboard/handleFileInsertion.ts
@@ -111,6 +111,8 @@ export async function handleFileInsertion<
     type: item.type,
   }));
 
+  let previousBlockId: string | undefined;
+
   for (const { file, type } of files) {
     // Gets file block corresponding to MIME type.
     let fileBlockType = "file";
@@ -146,7 +148,18 @@ export async function handleFileInsertion<
 
       let insertedBlockId: string | undefined = undefined;
 
-      if (event.type === "paste") {
+      const previousBlock = previousBlockId
+        ? editor.getBlock(previousBlockId)
+        : undefined;
+      if (previousBlock) {
+        // Resolve the event's insertion point only for the first file. Reusing
+        // it for every file reverses insertions after a nonempty block.
+        insertedBlockId = editor.insertBlocks(
+          [fileBlock],
+          previousBlock,
+          "after",
+        )[0].id;
+      } else if (event.type === "paste") {
         const currentBlock = editor.getTextCursorPosition().block;
         insertedBlockId = insertOrUpdateBlock(editor, currentBlock, fileBlock);
       } else if (event.type === "drop") {
@@ -195,6 +208,8 @@ export async function handleFileInsertion<
         return;
       }
 
+      previousBlockId = insertedBlockId;
+
       const updateData = await editor
         .uploadFile(file, insertedBlockId)
         .catch(() => undefined);