diff --git a/.changeset/cancel-during-transform.md b/.changeset/cancel-during-transform.md
new file mode 100644
index 000000000..0b8a896b2
--- /dev/null
+++ b/.changeset/cancel-during-transform.md
@@ -0,0 +1,5 @@
+---
+"dropzone": patch
+---
+
+Fix cancelling an upload while `transformFile` is still running. The file had no `xhr` yet, so it was grouped with every other file that had not started and the whole queue was cancelled with it — and the file itself was still sent once the transform finished.
diff --git a/packages/dropzone/src/dropzone.ts b/packages/dropzone/src/dropzone.ts
index 89131f7ec..c833c14d4 100644
--- a/packages/dropzone/src/dropzone.ts
+++ b/packages/dropzone/src/dropzone.ts
@@ -1345,7 +1345,12 @@ export default class Dropzone extends Emitter {
   // set to CANCELED.
   cancelUpload(file: DropzoneFile) {
     if (file.status === Dropzone.UPLOADING) {
-      let groupedFiles = this._getFilesWithXhr(file.xhr!);
+      // A file cancelled while `transformFile` is still running is already
+      // UPLOADING but has no request yet. Grouping by an undefined `xhr` then
+      // matched every other file that had not started either -- the whole
+      // queue -- and cancelled all of them. Without a request there is nobody
+      // to share it with, so the group is just this file. See #2231.
+      let groupedFiles = file.xhr ? this._getFilesWithXhr(file.xhr) : [file];
       for (let groupedFile of groupedFiles) {
         groupedFile.status = Dropzone.CANCELED;
       }
@@ -1395,6 +1400,14 @@ export default class Dropzone extends Emitter {
 
   uploadFiles(files: DropzoneFile[]) {
     this._transformFiles(files, (transformedFiles: (DropzoneFile | Blob)[]) => {
+      // `transformFile` is asynchronous and can take a while -- resizing or
+      // compressing a large image, or asking a server to presign the upload --
+      // and the user can cancel or remove the file in the meantime. Sending it
+      // now would upload data the UI already reported as canceled. See #2231.
+      if (files.every((file) => file.status === Dropzone.CANCELED)) {
+        return;
+      }
+
       // Options are often read straight out of markup or a config file, so
       // `chunkSize` can arrive as a string. `start + "2097152"` would then
       // concatenate instead of adding, and every chunk after the first would
diff --git a/packages/dropzone/test/unit-tests/all.js b/packages/dropzone/test/unit-tests/all.js
index 7d00c6452..4e4f4afea 100644
--- a/packages/dropzone/test/unit-tests/all.js
+++ b/packages/dropzone/test/unit-tests/all.js
@@ -692,6 +692,65 @@ describe("Dropzone", function () {
           }, 10);
         }));
 
+      it("should not cancel other queued files if the upload has not started yet", () =>
+        new Promise((done) => {
+          dropzone.accept = (file, done) => done();
+          // A transform that never finishes: the file is UPLOADING but has no
+          // xhr, which is what used to group it with every queued file.
+          dropzone.options.transformFile = () => {};
+          dropzone.options.parallelUploads = 1;
+
+          let uploading = getMockFile("text/html", "uploading");
+          let queued1 = getMockFile("text/html", "queued1");
+          let queued2 = getMockFile("text/html", "queued2");
+
+          dropzone.addFile(uploading);
+          dropzone.addFile(queued1);
+          dropzone.addFile(queued2);
+
+          return setTimeout(function () {
+            expect(uploading.status).toBe(Dropzone.UPLOADING);
+            expect(uploading.xhr).toBe(undefined);
+
+            let canceled = [];
+            dropzone.on("canceled", (file) => canceled.push(file.upload.filename));
+
+            dropzone.cancelUpload(uploading);
+
+            expect(uploading.status).toBe(Dropzone.CANCELED);
+            // Only the file the user cancelled. The queue then moves on, so
+            // the next one starts and the last one waits its turn.
+            expect(canceled).toEqual(["uploading"]);
+            expect([queued1.status, queued2.status]).toEqual([Dropzone.UPLOADING, Dropzone.QUEUED]);
+            return done();
+          }, 10);
+        }));
+
+      it("should not send a file that was canceled while it was being transformed", () =>
+        new Promise((done) => {
+          dropzone.accept = (file, done) => done();
+
+          let finishTransform = null;
+          dropzone.options.transformFile = (file, transformDone) =>
+            (finishTransform = () => transformDone(file));
+
+          let mockFile = getMockFile();
+          dropzone.addFile(mockFile);
+
+          return setTimeout(function () {
+            expect(mockFile.status).toBe(Dropzone.UPLOADING);
+
+            dropzone.cancelUpload(mockFile);
+            expect(mockFile.status).toBe(Dropzone.CANCELED);
+
+            // The transform only finishes now, after the user gave up on it.
+            finishTransform();
+
+            expect(mockFile.xhr).toBe(undefined);
+            return done();
+          }, 10);
+        }));
+
       it("should properly cancel all files with the same XHR if uploadMultiple is true", () =>
         new Promise((done) => {
           let mock1 = getMockFile();