diff --git a/frappe/public/js/frappe/file_uploader/FileUploader.vue b/frappe/public/js/frappe/file_uploader/FileUploader.vue
index 2420cc1bf5..10012c82ad 100644
--- a/frappe/public/js/frappe/file_uploader/FileUploader.vue
+++ b/frappe/public/js/frappe/file_uploader/FileUploader.vue
@@ -513,25 +513,36 @@ function check_restrictions(file) {
 
 	return is_correct_type && valid_file_size;
 }
+
+function set_loading_state(dialog, loading) {
+	let $btn = dialog?.get_primary_btn();
+	if (loading) {
+		$btn?.css("width", $btn.outerWidth());
+		$btn?.html(`<i class="fa fa-spinner fa-spin"></i>`);
+		$btn?.prop("disabled", true);
+		dialog?.get_secondary_btn().prop("disabled", true);
+	} else {
+		$btn?.css("width", "");
+		$btn?.html(__("Upload"));
+		$btn?.prop("disabled", false);
+		dialog?.get_secondary_btn().prop("disabled", false);
+	}
+}
 function upload_files(dialog) {
+	set_loading_state(dialog, true);
 	if (show_file_browser.value) {
-		return upload_via_file_browser();
-	}
-	if (show_web_link.value) {
-		return upload_via_web_link();
-	}
-	if (props.as_dataurl) {
-		return return_as_dataurl();
-	}
-	if (!files.value.length) {
+		promise = upload_via_file_browser();
+	} else if (show_web_link.value) {
+		promise = upload_via_web_link();
+	} else if (props.as_dataurl) {
+		promise = return_as_dataurl();
+	} else if (!files.value.length) {
 		frappe.msgprint(__("Please select a file first."));
-		return Promise.reject();
+		promise = Promise.reject();
+	} else {
+		promise = frappe.run_serially(files.value.map((file, i) => () => upload_file(file, i)));
 	}
-
-	dialog?.get_primary_btn().prop("disabled", true);
-	dialog?.get_secondary_btn().prop("disabled", true);
-
-	return frappe.run_serially(files.value.map((file, i) => () => upload_file(file, i)));
+	return promise.finally(() => set_loading_state(dialog, false));
 }
 function upload_via_file_browser() {
 	let selected_file = file_browser.value.selected_node;
@@ -548,12 +559,16 @@ function upload_via_file_browser() {
 function upload_via_web_link() {
 	let file_url = web_link.value.url;
 	if (!file_url) {
-		frappe.msgprint(__("Invalid URL"));
-		close_dialog.value = true;
+		web_link.value.invalid_input(__("Please enter a valid URL"));
+		return Promise.reject();
+	}
+	try {
+		file_url = decodeURI(file_url);
+	} catch (error) {
+		var error_message = error.message;
+		web_link.value.invalid_input(__(error_message));
 		return Promise.reject();
 	}
-	file_url = decodeURI(file_url);
-	close_dialog.value = true;
 	return upload_file({
 		file_url,
 	});
@@ -584,7 +599,6 @@ function upload_file(file, i) {
 		});
 		xhr.upload.addEventListener("load", (e) => {
 			file.uploading = false;
-			resolve();
 		});
 		xhr.addEventListener("error", (e) => {
 			file.failed = true;
@@ -593,6 +607,7 @@ function upload_file(file, i) {
 		xhr.onreadystatechange = () => {
 			if (xhr.readyState == XMLHttpRequest.DONE) {
 				if (xhr.status === 200) {
+					resolve();
 					file.request_succeeded = true;
 					let r = null;
 					let file_doc = null;
@@ -617,7 +632,11 @@ function upload_file(file, i) {
 					) {
 						close_dialog.value = true;
 					}
+					if (show_web_link.value && file.file_url) {
+						close_dialog.value = true;
+					}
 				} else if (xhr.status === 403) {
+					reject();
 					file.failed = true;
 					let response = parse_error_response(xhr.responseText);
 					file.error_message = __("Not permitted. {0}.", [response.error_message || ""]);
@@ -625,16 +644,29 @@ function upload_file(file, i) {
 						file.error_message += `\n${response.server_messages.join("\n")}`;
 					}
 				} else if (xhr.status === 413) {
+					reject();
 					file.failed = true;
 					file.error_message = __("Size exceeds the maximum allowed file size.");
 				} else if (xhr.status === 417) {
+					reject();
 					// regular frappe.throw() in backend
 					file.failed = true;
 					let response = parse_error_response(xhr.responseText);
 					file.error_message = response.server_messages.length
 						? response.server_messages.join("\n")
 						: __("File upload failed.");
+
+					if (show_web_link.value && web_link.value && file.file_url) {
+						web_link.value.invalid_input(__(file.error_message));
+					} else if (!files.value.includes(file)) {
+						frappe.msgprint({
+							title: __("Upload Failed"),
+							message: __(file.error_message),
+							indicator: "red",
+						});
+					}
 				} else {
+					reject();
 					file.failed = true;
 					let detail =
 						xhr.statusText ||
diff --git a/frappe/public/js/frappe/file_uploader/WebLink.vue b/frappe/public/js/frappe/file_uploader/WebLink.vue
index 7e731f0dc8..ef601a7796 100644
--- a/frappe/public/js/frappe/file_uploader/WebLink.vue
+++ b/frappe/public/js/frappe/file_uploader/WebLink.vue
@@ -1,28 +1,42 @@
 <template>
-	<div class="file-web-link margin-bottom">
+	<div class="file-web-link" :style="{ 'margin-bottom': error_message ? '0' : '0.5rem' }">
 		<a href class="text-muted text-medium" @click.prevent="emit('hide-web-link')">
 			{{ __("← Back to upload files") }}
 		</a>
 		<div class="input-group">
 			<input
+				ref="web_link_input"
 				type="text"
-				class="form-control"
+				class="form-control mr-1"
+				:class="{ 'is-invalid': error_message }"
 				:placeholder="__('Attach a web link')"
 				v-model="url"
 			/>
 		</div>
+		<div class="text-small text-danger pt-1" v-if="error_message">{{ error_message }}</div>
 	</div>
 </template>
 
 <script setup>
-import { ref } from "vue";
+import { ref, watch } from "vue";
 
 // emits
 let emit = defineEmits(["hide-web-link"]);
 
 let url = ref("");
+let web_link_input = ref(null);
+let error_message = ref("");
 
-defineExpose({ url });
+watch(url, () => {
+	error_message.value = "";
+});
+
+function invalid_input(error) {
+	error_message.value = error;
+	web_link_input.value?.focus();
+}
+
+defineExpose({ url, invalid_input });
 </script>
 
 <style scoped>