diff --git a/src/assets/translations/en.json b/src/assets/translations/en.json
index 19fd4cb..cd12ab2 100644
--- a/src/assets/translations/en.json
+++ b/src/assets/translations/en.json
@@ -66,7 +66,8 @@
     "file_prefix": "File: ",
     "edited": "(edited)",
     "download_progress": "{percentage}% downloaded",
-    "upload_file_too_large": "File is too large to upload!",
+    "upload_file_too_large": "Maximum file size of ({configFormattedUploadSize}) exceeded. File is too large to upload!",
+    "upload_exceeded_file_limit": "File: ({exceededFile}) ({formattedUploadSize}) exceeds maximum limit.",
     "upload_progress": "Uploaded {count}",
     "upload_progress_with_total": "Uploaded {count} of {total}",
     "user_changed_room_history": "{user} made room history {type}",
diff --git a/src/components/Chat.vue b/src/components/Chat.vue
index bbbf80b..57bf4f3 100644
--- a/src/components/Chat.vue
+++ b/src/components/Chat.vue
@@ -217,9 +217,16 @@
                   <span v-if="currentImageInput && currentImageInput.scaled && currentImageInput.useScaled">
                     {{ currentImageInput.scaledDimensions.width }} x {{ currentImageInput.scaledDimensions.height }}</span>
                   <span v-else-if="currentImageInput && currentImageInput.dimensions">
-                    {{ currentImageInput.dimensions.width }} x {{ currentImageInput.dimensions.height }}</span>
+                    {{ currentImageInput.dimensions.width }} x {{ currentImageInput.dimensions.height }}
+                  </span>
+
                   <span v-if="currentImageInput && currentImageInput.scaled && currentImageInput.useScaled">
-                    ({{ formatBytes(currentImageInput.scaledSize) }})</span>
+                    ({{ formatBytes(currentImageInput.scaledSize) }})
+                  </span>
+                  <span v-else>
+                    ({{ formatBytes(currentImageInput.actualSize) }})
+                  </span>
+
                   <v-switch v-if="currentImageInput && currentImageInput.scaled" :label="$t('message.scale_image')"
                     v-model="currentImageInput.useScaled" />
                 </div>
@@ -241,6 +248,7 @@
           <v-card-actions>
             <v-spacer>
               <div v-if="currentSendError">{{ currentSendError }}</div>
+              <div v-if="currentSendErrorExceededFile" class="red--text">{{ currentSendErrorExceededFile }}</div>
               <div v-else>{{ currentSendProgress }}</div>
             </v-spacer>
             <v-btn color="primary" text @click="cancelSendAttachment" id="btn-attachment-cancel">
@@ -420,6 +428,7 @@ export default {
       currentSendProgress: null,
       currentSendShowSendButton: true,
       currentSendError: null,
+      currentSendErrorExceededFile: null,
       showEmojiPicker: false,
       selectedEvent: null,
       editedEvent: null,
@@ -519,10 +528,10 @@ export default {
   computed: {
     notificationCount,
     nonImageFiles() {
-      return this.isCurrentFileInputsAnArray && this.currentFileInputs.filter(file => !file.type.includes("image/"))
+      return this.isCurrentFileInputsAnArray && this.currentFileInputs.filter(file => !file?.type.includes("image/"))
     },
     imageFiles() {
-      return this.isCurrentFileInputsAnArray && this.currentFileInputs.filter(file => file.type.includes("image/"))
+      return this.isCurrentFileInputsAnArray && this.currentFileInputs.filter(file => file?.type.includes("image/"))
     },
     isCurrentFileInputsAnArray() {
       return Array.isArray(this.currentFileInputs)
@@ -1098,15 +1107,18 @@ export default {
       this.$refs.attachment.click();
     },
 
-    optimizeImage(e,event,file) {
-      file.image = e.target.result;
-      file.dimensions = null;
+    optimizeImage(evt,file) {
+      let fileObj = {}
+      fileObj.image = evt.target.result;
+      fileObj.dimensions = null;
+      fileObj.type = file.type;
+      fileObj.actualSize = file.size;
       try {
-        file.dimensions = sizeOf(dataUriToBuffer(e.target.result));
+        fileObj.dimensions = sizeOf(dataUriToBuffer(evt.target.result));
 
         // Need to resize?
-        const w = file.dimensions.width;
-        const h = file.dimensions.height;
+        const w = fileObj.dimensions.width;
+        const h = fileObj.dimensions.height;
         if (w > 640 || h > 640) {
           var aspect = w / h;
           var newWidth = parseInt((w > h ? 640 : 640 * aspect).toFixed());
@@ -1118,19 +1130,19 @@ export default {
             outputType: "blob",
           });
           imageResize
-            .play(event.target)
+            .play(evt.target.result)
             .then((img) => {
               Vue.set(
-                file,
+                fileObj,
                 "scaled",
                 new File([img], file.name, {
                   type: img.type,
                   lastModified: Date.now(),
                 })
               );
-              Vue.set(file, "useScaled", true);
-              Vue.set(file, "scaledSize", img.size);
-              Vue.set(file, "scaledDimensions", {
+              Vue.set(fileObj, "useScaled", true);
+              Vue.set(fileObj, "scaledSize", img.size);
+              Vue.set(fileObj, "scaledDimensions", {
                 width: newWidth,
                 height: newHeight,
               });
@@ -1142,24 +1154,19 @@ export default {
       } catch (error) {
         console.error("Failed to get image dimensions: " + error);
       }
-      return file
+      return fileObj
     },
-    handleFileReader(event, file) {
+    handleFileReader(file) {
       if (file) {
+        let optimizedFileObj;
         var reader = new FileReader();
-        reader.onload = (e) => {
+        reader.onload = (evt) => {
           if (file.type.startsWith("image/")) {
-            this.optimizeImage(e, event, file)
+            optimizedFileObj = this.optimizeImage(evt, file)
+          } else {
+            optimizedFileObj = file
           }
-          this.$matrix.matrixClient.getMediaConfig().then((config) => {
-            this.currentFileInputs = Array.isArray(this.currentFileInputs) ? [...this.currentFileInputs, file] : [file];
-            if (config["m.upload.size"] && file.size > config["m.upload.size"]) {
-              this.currentSendError = this.$t("message.upload_file_too_large");
-              this.currentSendShowSendButton = false;
-            } else {
-              this.currentSendShowSendButton = true;
-            }
-          });
+          this.currentFileInputs = Array.isArray(this.currentFileInputs) ? [...this.currentFileInputs, optimizedFileObj] : [optimizedFileObj];
         };
         reader.readAsDataURL(file);
       }
@@ -1168,7 +1175,27 @@ export default {
      * Handle picked attachment
      */
     handlePickedAttachment(event) {
-      Object.values(event.target.files).forEach(file => this.handleFileReader(event, file));
+        const uploadedFiles = Object.values(event.target.files);
+
+        this.$matrix.matrixClient.getMediaConfig().then((config) => {
+          const configUploadSize = config["m.upload.size"];
+          const configFormattedUploadSize = this.formatBytes(configUploadSize);
+
+          uploadedFiles.every(file => {
+            if (configUploadSize && file.size > configUploadSize) {
+              this.currentSendError = this.$t("message.upload_file_too_large", { configFormattedUploadSize });
+              this.currentSendErrorExceededFile = this.$t("message.upload_exceeded_file_limit", { exceededFile: file.name, formattedUploadSize: this.formatBytes(file.size) });
+              this.currentSendShowSendButton = false;
+              return false;
+            } else {
+              this.currentSendShowSendButton = true;
+            }
+            return true;
+          });
+
+          uploadedFiles.forEach(file => this.handleFileReader(file));
+
+        });
     },
 
     showStickerPicker() {
@@ -1210,8 +1237,10 @@ export default {
       .catch((err) => {
         if (err.name === "AbortError" || err === "Abort") {
           this.currentSendError = null;
+          this.currentSendErrorExceededFile = null;
         } else {
           this.currentSendError = err.LocaleString();
+          this.currentSendErrorExceededFile = err.LocaleString();
         }
         this.currentSendOperation = null;
         this.currentSendProgress = null;
@@ -1228,6 +1257,7 @@ export default {
       this.currentFileInputs = null;
       this.currentSendProgress = null;
       this.currentSendError = null;
+      this.currentSendErrorExceededFile = null;
     },
 
     addAttachment(file) {