diff --git a/src/ui/UserPortal/components/ChatInput.vue b/src/ui/UserPortal/components/ChatInput.vue
index 2d0c6de9a5..0d730a20f4 100644
--- a/src/ui/UserPortal/components/ChatInput.vue
+++ b/src/ui/UserPortal/components/ChatInput.vue
@@ -4,10 +4,34 @@
 			<i class="pi pi-info-circle tooltip-component" v-tooltip="'Use Shift+Enter to add a new line'"></i>
 			<Button
 				icon="pi pi-paperclip"
+				label=""
 				class="file-upload-button"
 				style="height: 100%;"
-				@click="showFileUploadDialog = true"
+				@click="toggleFileAttachmentOverlay"
+				:badge="$appStore.attachments.length.toString() || null"
 			/>
+			<OverlayPanel ref="fileAttachmentPanel">
+				<div class="attached-files-container">
+					<h2 style="margin-bottom: 0px;">Attached Files</h2>
+					<div class="attached-files" v-for="file in $appStore.attachments" v-if="$appStore.attachments.length">
+						<div class="file-name">{{ file.fileName }}</div>
+						<div class="file-remove">
+							<Button icon="pi pi-times" severity="danger" text rounded aria-label="Remove attachment" @click="removeAttachment(file)" />
+						</div>
+					</div>
+					<div v-else>
+						No files attached
+					</div>
+				</div>
+				<div class="p-d-flex p-jc-end">
+					<Button
+						label="Upload File"
+						icon="pi pi-upload"
+						class="p-button-primary"
+						@click="showFileUploadDialog = true"
+					/>
+				</div>
+			</OverlayPanel>
 			<Dialog v-model:visible="showFileUploadDialog" header="Upload File" modal>
 				<FileUpload
 					accept="audio/mpeg,audio/wav"
@@ -167,7 +191,15 @@ export default {
 			} catch (error) {
 				this.$toast.add({ severity: 'error', summary: 'Error', detail: `File upload failed. ${error.message}` });
 			}
-		}
+		},
+
+		toggleFileAttachmentOverlay(event: any) {
+			this.$refs.fileAttachmentPanel.toggle(event);
+		},
+
+		removeAttachment(file: any) {
+			this.$appStore.attachments = this.$appStore.attachments.filter((f) => f !== file);
+		},
 	},
 };
 </script>
@@ -260,6 +292,22 @@ export default {
 .file-upload-button {
 	height: 100%;
 }
+
+.attached-files-container {
+	padding-bottom: 1rem;
+}
+
+.attached-files {
+	display: flex;
+    flex-direction: row;
+    align-items: center;
+    justify-content: space-between;
+    flex-wrap: nowrap;
+}
+
+.file-remove {
+	margin-left: 1rem;
+}
 </style>
 
 <style lang="scss">
diff --git a/src/ui/UserPortal/js/api.ts b/src/ui/UserPortal/js/api.ts
index 4053459d56..9635d6616d 100644
--- a/src/ui/UserPortal/js/api.ts
+++ b/src/ui/UserPortal/js/api.ts
@@ -61,13 +61,14 @@ export default {
 
 		try {
 			const response = await $fetch(`${this.apiUrl}${url}`, options);
-			return response;
+			if (response.status >= 400) {
+                throw response;
+            }
+            return response;
 		} catch (error) {
 			// If the error is an HTTP error, extract the message directly.
-			if (error.data) {
-				throw new Error(error.data.message || error.data || 'Unknown error occurred');
-			}
-			throw error;
+			const errorMessage = formatError(error);
+            throw new Error(errorMessage);
 		}
 	},
 
@@ -201,19 +202,29 @@ export default {
 	 * @returns The ObjectID of the uploaded attachment.
 	 */
 	async uploadAttachment(file: FormData) {
-		try {
-			const response = await this.fetch('/attachments/upload', {
-				method: 'POST',
-				body: file,
-			});
-	
-			if (response.error || response.status >= 400) {
-				throw new Error(response.message || 'Unknown error occurred');
-			}
-	
-			return response;
-		} catch (error) {
-			throw error;
-		}
+		const response = await this.fetch('/attachments/upload', {
+			method: 'POST',
+			body: file,
+		});
+
+		return response;
 	},
 };
+
+function formatError(error: any): string {
+    if (error.errors || error.data?.errors) {
+		const errors = error.errors || error.data.errors;
+        // Flatten the error messages and join them into a single string
+        return Object.values(errors).flat().join(' ');
+    }
+	if (error.data) {
+		return error.data.message || error.data || 'An unknown error occurred';
+	}
+    if (error.message) {
+        return error.message;
+    }
+    if (typeof error === 'string') {
+        return error;
+    }
+    return 'An unknown error occurred';
+}
diff --git a/src/ui/UserPortal/js/types/index.ts b/src/ui/UserPortal/js/types/index.ts
index 3599cd84c9..7a502e0bd1 100644
--- a/src/ui/UserPortal/js/types/index.ts
+++ b/src/ui/UserPortal/js/types/index.ts
@@ -73,3 +73,8 @@ export interface OrchestrationRequest {
 	settings?: OrchestrationSettings;
 	attachments?: string[];
 }
+
+export interface Attachment {
+	id: string;
+	fileName: string;
+}
diff --git a/src/ui/UserPortal/plugins/primevue.ts b/src/ui/UserPortal/plugins/primevue.ts
index f49096358e..b8d7f839fb 100644
--- a/src/ui/UserPortal/plugins/primevue.ts
+++ b/src/ui/UserPortal/plugins/primevue.ts
@@ -12,6 +12,10 @@ import Divider from 'primevue/divider';
 import Dropdown from 'primevue/dropdown';
 import Avatar from 'primevue/avatar';
 import FileUpload from 'primevue/fileupload';
+import OverlayPanel from 'primevue/overlaypanel';
+import Badge from 'primevue/badge';
+import BadgeDirective from 'primevue/badgedirective';
+
 
 import { defineNuxtPlugin } from '#app';
 
@@ -28,6 +32,9 @@ export default defineNuxtPlugin((nuxtApp) => {
 	nuxtApp.vueApp.component('Dropdown', Dropdown);
 	nuxtApp.vueApp.component('Avatar', Avatar);
 	nuxtApp.vueApp.component('FileUpload', FileUpload);
+	nuxtApp.vueApp.component('OverlayPanel', OverlayPanel);
+	nuxtApp.vueApp.component('Badge', Badge);
+	nuxtApp.vueApp.directive('badge', BadgeDirective);
 
 	nuxtApp.vueApp.use(ToastService);
 	nuxtApp.vueApp.directive('tooltip', Tooltip);
diff --git a/src/ui/UserPortal/stores/appStore.ts b/src/ui/UserPortal/stores/appStore.ts
index 2db237ac45..5a59e50c6f 100644
--- a/src/ui/UserPortal/stores/appStore.ts
+++ b/src/ui/UserPortal/stores/appStore.ts
@@ -1,7 +1,7 @@
 import { defineStore } from 'pinia';
 import { useAppConfigStore } from './appConfigStore';
 import { useAuthStore } from './authStore';
-import type { Session, Message, Agent, ResourceProviderGetResult } from '@/js/types';
+import type { Session, Message, Agent, ResourceProviderGetResult, Attachment } from '@/js/types';
 import api from '@/js/api';
 
 export const useAppStore = defineStore('app', {
@@ -13,7 +13,7 @@ export const useAppStore = defineStore('app', {
 		agents: [] as ResourceProviderGetResult<Agent>[],
 		selectedAgents: new Map(),
 		lastSelectedAgent: null as ResourceProviderGetResult<Agent> | null,
-		attachments: [] as String[],
+		attachments: [] as Attachment[],
 	}),
 
 	getters: {},
@@ -170,7 +170,7 @@ export const useAppStore = defineStore('app', {
 				this.currentSession!.id,
 				text,
 				this.getSessionAgent(this.currentSession!).resource,
-				[...this.attachments.map(String)], // Convert attachments to an array of strings
+				this.attachments.map(attachment => String(attachment.id)), // Convert attachments to an array of strings
 			);
 			await this.getMessages();
 
@@ -228,9 +228,10 @@ export const useAppStore = defineStore('app', {
 		async uploadAttachment(file: FormData) {
 			try {
 				const id = await api.uploadAttachment(file);
+				const fileName = file.get('file')?.name;
 				// this.attachments.push(id);
 				// For now, we want to just replace the attachments with the new one.
-				this.attachments = [id as string];
+				this.attachments = [{ id, fileName}];
 				return id;
 			} catch (error) {
 				throw error;