diff --git a/packages/upload/src/vaadin-upload.js b/packages/upload/src/vaadin-upload.js
index 9911e87145..3d3e3835eb 100644
--- a/packages/upload/src/vaadin-upload.js
+++ b/packages/upload/src/vaadin-upload.js
@@ -432,6 +432,26 @@ class Upload extends ElementMixin(ThemableMixin(PolymerElement)) {
     };
   }
 
+  /** @private */
+  get __acceptRegexp() {
+    if (!this.accept) {
+      return null;
+    }
+    const processedTokens = this.accept.split(',').map((token) => {
+      let processedToken = token.trim();
+      // Escape regex operators common to mime types
+      processedToken = processedToken.replace(/[+.]/g, '\\$&');
+      // Make extension patterns match the end of the file name
+      if (processedToken.startsWith('\\.')) {
+        processedToken = `.*${processedToken}$`;
+      }
+      // Handle star (*) wildcards
+      return processedToken.replace(/\/\*/g, '/.*');
+    });
+    // Create accept regex
+    return new RegExp(`^(${processedTokens.join('|')})$`, 'i');
+  }
+
   /** @protected */
   ready() {
     super.ready();
@@ -779,12 +799,8 @@ class Upload extends ElementMixin(ThemableMixin(PolymerElement)) {
       );
       return;
     }
-    const fileExt = file.name.match(/\.[^.]*$|$/)[0];
-    // Escape regex operators common to mime types
-    const escapedAccept = this.accept.replace(/[+.]/g, '\\$&');
-    // Create accept regex that can match comma separated patterns, star (*) wildcards
-    const re = new RegExp(`^(${escapedAccept.replace(/[, ]+/g, '|').replace(/\/\*/g, '/.*')})$`, 'i');
-    if (this.accept && !(re.test(file.type) || re.test(fileExt))) {
+    const re = this.__acceptRegexp;
+    if (re && !(re.test(file.type) || re.test(file.name))) {
       this.dispatchEvent(
         new CustomEvent('file-reject', {
           detail: { file, error: this.i18n.error.incorrectFileType },
diff --git a/packages/upload/test/adding-files.test.js b/packages/upload/test/adding-files.test.js
index 55b624cab3..f962ccf548 100644
--- a/packages/upload/test/adding-files.test.js
+++ b/packages/upload/test/adding-files.test.js
@@ -251,6 +251,20 @@ describe('file list', () => {
       expect(upload.files.length).to.equal(1);
     });
 
+    it('should allow files with extensions containing multiple dots', () => {
+      upload.accept = 'image/*,.bar.baz,video/*';
+      file.name = 'foo.bar.baz';
+      upload._addFiles([file]);
+      expect(upload.files).to.have.lengthOf(1);
+    });
+
+    it('should reject files that have partial extension match', () => {
+      upload.accept = 'image/*,.bar.baz,video/*';
+      file.name = 'foo.baz';
+      upload._addFiles([file]);
+      expect(upload.files).to.have.lengthOf(0);
+    });
+
     it('should allow files with correct mime type', () => {
       upload.accept = 'application/x-octet-stream';
       upload._addFiles([file]);