diff --git a/app/assets/javascripts/discourse/app/lib/text.js b/app/assets/javascripts/discourse/app/lib/text.js
index 3de5338080e..544a71953e7 100644
--- a/app/assets/javascripts/discourse/app/lib/text.js
+++ b/app/assets/javascripts/discourse/app/lib/text.js
@@ -4,6 +4,7 @@ import { sanitize as textSanitize } from "pretty-text/sanitizer";
 import deprecated from "discourse-common/lib/deprecated";
 import { getURLWithCDN } from "discourse-common/lib/get-url";
 import { helperContext } from "discourse-common/lib/helpers";
+import I18n from "discourse-i18n";
 
 async function withEngine(name, ...args) {
   const engine = await import("discourse/static/markdown-it");
@@ -136,3 +137,18 @@ export function excerpt(cooked, length) {
 
   return result;
 }
+
+export function humanizeList(listItems) {
+  const items = Array.from(listItems);
+  const last = items.pop();
+
+  if (items.length === 0) {
+    return last;
+  } else {
+    return [
+      items.join(I18n.t("word_connector.comma")),
+      I18n.t("word_connector.last_item"),
+      last,
+    ].join(" ");
+  }
+}
diff --git a/app/assets/javascripts/discourse/app/lib/uploads.js b/app/assets/javascripts/discourse/app/lib/uploads.js
index 7f010b23be5..6e7efed8f2a 100644
--- a/app/assets/javascripts/discourse/app/lib/uploads.js
+++ b/app/assets/javascripts/discourse/app/lib/uploads.js
@@ -1,3 +1,4 @@
+import { humanizeList } from "discourse/lib/text";
 import { isAppleDevice } from "discourse/lib/utilities";
 import deprecated from "discourse-common/lib/deprecated";
 import { getOwnerWithFallback } from "discourse-common/lib/get-owner";
@@ -302,6 +303,12 @@ export function getUploadMarkdown(upload) {
   }
 }
 
+export function displayErrorForBulkUpload(errors) {
+  const fileNames = humanizeList(errors.mapBy("fileName"));
+
+  dialog.alert(I18n.t("post.errors.upload", { file_name: fileNames }));
+}
+
 export function displayErrorForUpload(data, siteSettings, fileName) {
   if (!fileName) {
     deprecated(
diff --git a/app/assets/javascripts/discourse/app/mixins/composer-upload-uppy.js b/app/assets/javascripts/discourse/app/mixins/composer-upload-uppy.js
index 0a8438b6c5b..8315d344543 100644
--- a/app/assets/javascripts/discourse/app/mixins/composer-upload-uppy.js
+++ b/app/assets/javascripts/discourse/app/mixins/composer-upload-uppy.js
@@ -11,6 +11,7 @@ import { cacheShortUploadUrl } from "pretty-text/upload-short-url";
 import { updateCsrfToken } from "discourse/lib/ajax";
 import {
   bindFileInputChangeListener,
+  displayErrorForBulkUpload,
   displayErrorForUpload,
   getUploadMarkdown,
   validateUploadedFile,
@@ -99,6 +100,7 @@ export default Mixin.create(ExtendableUploader, UppyS3Multipart, {
 
   _bindUploadTarget() {
     this.set("inProgressUploads", []);
+    this.set("bufferedUploadErrors", []);
     this.placeholders = {};
     this._preProcessorStatus = {};
     this.editorEl = this.element.querySelector(this.editorClass);
@@ -352,6 +354,7 @@ export default Mixin.create(ExtendableUploader, UppyS3Multipart, {
               this.appEvents.trigger(
                 `${this.composerEventPrefix}:all-uploads-complete`
               );
+              this._displayBufferedErrors();
               this._reset();
             }
           }
@@ -403,11 +406,11 @@ export default Mixin.create(ExtendableUploader, UppyS3Multipart, {
     file.meta.error = error;
 
     if (!this.userCancelled) {
-      displayErrorForUpload(response || error, this.siteSettings, file.name);
+      this._bufferUploadError(response || error, file.name);
       this.appEvents.trigger(`${this.composerEventPrefix}:upload-error`, file);
     }
-
     if (this.inProgressUploads.length === 0) {
+      this._displayBufferedErrors();
       this._reset();
     }
   },
@@ -419,6 +422,24 @@ export default Mixin.create(ExtendableUploader, UppyS3Multipart, {
     );
   },
 
+  _displayBufferedErrors() {
+    if (this.bufferedUploadErrors.length === 0) {
+      return;
+    } else if (this.bufferedUploadErrors.length === 1) {
+      displayErrorForUpload(
+        this.bufferedUploadErrors[0].data,
+        this.siteSettings,
+        this.bufferedUploadErrors[0].fileName
+      );
+    } else {
+      displayErrorForBulkUpload(this.bufferedUploadErrors);
+    }
+  },
+
+  _bufferUploadError(data, fileName) {
+    this.bufferedUploadErrors.push({ data, fileName });
+  },
+
   _setupPreProcessors() {
     const checksumPreProcessor = {
       pluginClass: UppyChecksum,
@@ -561,6 +582,7 @@ export default Mixin.create(ExtendableUploader, UppyS3Multipart, {
       isProcessingUpload: false,
       isCancellable: false,
       inProgressUploads: [],
+      bufferedUploadErrors: [],
     });
     this._resetPreProcessors();
     this.fileInputEl.value = "";
diff --git a/app/assets/javascripts/discourse/tests/acceptance/composer-uploads-uppy-test.js b/app/assets/javascripts/discourse/tests/acceptance/composer-uploads-uppy-test.js
index 5b7266fa748..66e8b9c6fa7 100644
--- a/app/assets/javascripts/discourse/tests/acceptance/composer-uploads-uppy-test.js
+++ b/app/assets/javascripts/discourse/tests/acceptance/composer-uploads-uppy-test.js
@@ -530,6 +530,53 @@ acceptance("Uppy Composer Attachment - Upload Error", function (needs) {
   });
 });
 
+acceptance(
+  "Uppy Composer Attachment - Multiple Upload Errors",
+  function (needs) {
+    needs.user();
+    needs.pretender((server, helper) => {
+      server.post("/uploads.json", () => {
+        return helper.response(500, {
+          success: false,
+        });
+      });
+    });
+    needs.settings({
+      simultaneous_uploads: 2,
+      allow_uncategorized_topics: true,
+    });
+
+    test("should show a consolidated message for multiple failed uploads", async function (assert) {
+      await visit("/");
+      await click("#create-topic");
+      const appEvents = loggedInUser().appEvents;
+      const image = createFile("meme1.png");
+      const image1 = createFile("meme2.png");
+      const done = assert.async();
+
+      appEvents.on("composer:upload-error", async () => {
+        await settled();
+
+        if (!query(".dialog-body")) {
+          return;
+        }
+
+        assert.strictEqual(
+          query(".dialog-body").textContent.trim(),
+          "Sorry, there was an error uploading meme1.png and meme2.png. Please try again.",
+          "it should show a consolidated error dialog"
+        );
+
+        await click(".dialog-footer .btn-primary");
+
+        done();
+      });
+
+      appEvents.trigger("composer:add-files", [image, image1]);
+    });
+  }
+);
+
 acceptance("Uppy Composer Attachment - Upload Handler", function (needs) {
   needs.user();
   needs.pretender(pretender);
diff --git a/config/locales/client.en.yml b/config/locales/client.en.yml
index 8403f7a606b..a2c57341b3e 100644
--- a/config/locales/client.en.yml
+++ b/config/locales/client.en.yml
@@ -163,6 +163,7 @@ en:
 
     word_connector:
       comma: ", "
+      last_item: "and"
 
     action_codes:
       public_topic: "Made this topic public %{when}"