diff --git a/src/components/NewMessage/NewMessage.vue b/src/components/NewMessage/NewMessage.vue
index 1a2c74ace44..cdfabd58a57 100644
--- a/src/components/NewMessage/NewMessage.vue
+++ b/src/components/NewMessage/NewMessage.vue
@@ -256,7 +256,7 @@ export default {
 		},
 	},
 
-	emits: ['sent', 'failure'],
+	emits: ['sent', 'failure', 'upload'],
 
 	expose: ['focusInput'],
 
@@ -400,7 +400,8 @@ export default {
 
 	mounted() {
 		EventBus.$on('focus-chat-input', this.focusInput)
-		EventBus.$on('upload-start', this.handleUploadStart)
+		EventBus.$on('upload-start', this.handleUploadSideEffects)
+		EventBus.$on('upload-discard', this.handleUploadSideEffects)
 		EventBus.$on('retry-message', this.handleRetryMessage)
 		this.text = this.$store.getters.currentMessageInput(this.token)
 
@@ -411,7 +412,8 @@ export default {
 
 	beforeDestroy() {
 		EventBus.$off('focus-chat-input', this.focusInput)
-		EventBus.$off('upload-start', this.handleUploadStart)
+		EventBus.$off('upload-start', this.handleUploadSideEffects)
+		EventBus.$off('upload-discard', this.handleUploadSideEffects)
 		EventBus.$off('retry-message', this.handleRetryMessage)
 	},
 
@@ -453,14 +455,14 @@ export default {
 			}
 		},
 
-		handleUploadStart() {
+		handleUploadSideEffects() {
 			if (this.upload) {
 				return
 			}
 			this.$nextTick(() => {
-				// reset main input in chat view after upload file with caption
+				// reset or fill main input in chat view from the store
 				this.text = this.$store.getters.currentMessageInput(this.token)
-				// refocus on upload start as the user might want to type again while the upload is running
+				// refocus input as the user might want to type further
 				this.focusInput()
 			})
 		},
@@ -482,9 +484,17 @@ export default {
 			}
 
 			if (this.upload) {
-				this.$emit('sent', this.text)
+				// Clear input content from store
 				this.$store.dispatch('setCurrentMessageInput', { token: this.token, text: '' })
-				return
+
+				if (this.$store.getters.getInitialisedUploads(this.$store.getters.currentUploadId).length) {
+					// If dialog contains files to upload, delegate sending
+					this.$emit('upload', this.text)
+					return
+				} else {
+					// Dismiss dialog, process as normal message sending otherwise
+					this.$emit('sent')
+				}
 			}
 
 			if (this.hasText) {
diff --git a/src/components/NewMessage/NewMessageUploadEditor.vue b/src/components/NewMessage/NewMessageUploadEditor.vue
index b5c3acb7577..0f0951547b1 100644
--- a/src/components/NewMessage/NewMessageUploadEditor.vue
+++ b/src/components/NewMessage/NewMessageUploadEditor.vue
@@ -82,7 +82,8 @@
 				:token="token"
 				:container="modalContainerId"
 				:aria-label="t('spreed', 'Post message')"
-				@sent="handleUpload"
+				@upload="handleUpload"
+				@sent="handleDismiss"
 				@failure="handleDismiss" />
 		</div>
 	</NcModal>
diff --git a/src/store/fileUploadStore.js b/src/store/fileUploadStore.js
index 8090310cd90..449f14e734c 100644
--- a/src/store/fileUploadStore.js
+++ b/src/store/fileUploadStore.js
@@ -263,6 +263,7 @@ const actions = {
 		if (state.currentUploadId === uploadId) {
 			commit('setCurrentUploadId', undefined)
 		}
+		EventBus.$emit('upload-discard')
 
 		commit('discardUpload', { uploadId })
 	},