diff --git a/src/js/apps/patients/sidebar/action-sidebar_app.js b/src/js/apps/patients/sidebar/action-sidebar_app.js
index 449724780..e150aecb1 100644
--- a/src/js/apps/patients/sidebar/action-sidebar_app.js
+++ b/src/js/apps/patients/sidebar/action-sidebar_app.js
@@ -236,7 +236,10 @@ export default App.extend(extend({
     });
     attachment.upload(file);
 
-    Radio.request('ws', 'add', attachment);
+    this.listenTo(attachment, 'upload:success', uploadedAttachment => {
+      this.action.addFileRelationship(uploadedAttachment);
+      Radio.request('ws', 'add', uploadedAttachment);
+    });
 
     this.listenTo(attachment, 'upload:failed', () => {
       Radio.request('alert', 'show:error', intl.patients.sidebar.actionSidebarApp.uploadError);
@@ -245,6 +248,8 @@ export default App.extend(extend({
   onRemoveAttachment(model) {
     model.destroy();
 
+    this.action.removeFileRelationship(model);
+
     Radio.request('ws', 'unsubscribe', model);
   },
   addSubscriptions() {
diff --git a/src/js/entities-service/entities/actions.js b/src/js/entities-service/entities/actions.js
index a176e0d84..157122437 100644
--- a/src/js/entities-service/entities/actions.js
+++ b/src/js/entities-service/entities/actions.js
@@ -64,8 +64,7 @@ const _Model = BaseModel.extend({
         _download: attributes.urls.download,
       });
 
-      const newFilesRelationship = [...this.get('_files'), { id: file.id, type: 'files' }];
-      this.set({ _files: newFilesRelationship });
+      this.addFileRelationship(attachmentModel);
 
       this.trigger('ws:add:attachment', attachmentModel);
     },
@@ -250,7 +249,12 @@ const _Model = BaseModel.extend({
 
     return !!size(programAction.get('allowed_uploads'));
   },
-  removeAttachment(resource) {
+  addFileRelationship(resource) {
+    const newFilesRelationship = [...this.get('_files'), { id: resource.id, type: 'files' }];
+
+    this.set({ _files: newFilesRelationship });
+  },
+  removeFileRelationship(resource) {
     const files = this.get('_files');
     const newFilesRelationship = files.filter(file => {
       return file.id !== resource.id;
diff --git a/src/js/entities-service/entities/files.js b/src/js/entities-service/entities/files.js
index 3c7995a4e..6555b8e4e 100644
--- a/src/js/entities-service/entities/files.js
+++ b/src/js/entities-service/entities/files.js
@@ -28,7 +28,7 @@ const _Model = BaseModel.extend({
     },
     FileRemoved({ resource }) {
       const action = Radio.request('entities', 'actions:model', this.get('_action'));
-      action.removeAttachment(resource);
+      action.removeFileRelationship(resource);
 
       this.destroy({ isDeleted: true });
     },
@@ -66,6 +66,9 @@ const _Model = BaseModel.extend({
     this.createUpload(file.name)
       .then(() => this.putFile(file))
       .then(() => this.fetchFile())
+      .then(uploadedFile => {
+        this.trigger('upload:success', uploadedFile);
+      })
       .catch(() => {
         this.trigger('upload:failed');
         this.destroy();
diff --git a/test/integration/patients/sidebar/action-sidebar.js b/test/integration/patients/sidebar/action-sidebar.js
index 9ffaf7452..23fe37231 100644
--- a/test/integration/patients/sidebar/action-sidebar.js
+++ b/test/integration/patients/sidebar/action-sidebar.js
@@ -968,6 +968,161 @@ context('action sidebar', function() {
       });
   });
 
+  specify('action attachments - show/hide icon in action list items', function() {
+    const testPatient = getPatient();
+
+    const testProgramAction = getProgramAction({
+      attributes: {
+        allowed_uploads: ['pdf'],
+      },
+    });
+
+    const testAction = getAction({
+      relationships: {
+        'files': getRelationship([], 'files'),
+        'patient': getRelationship(testPatient),
+        'program-action': getRelationship(testProgramAction),
+        'state': getRelationship(stateTodo),
+      },
+    });
+
+    cy
+      .routesForPatientAction()
+      .routeSettings(fx => {
+        fx.data.push({ id: 'upload_attachments', attributes: { value: true } });
+
+        return fx;
+      })
+      .routePatient(fx => {
+        fx.data = testPatient;
+
+        return fx;
+      })
+      .routePatientActions(fx => {
+        fx.data = [testAction];
+
+        return fx;
+      })
+      .routePatientFlows(fx => {
+        fx.data = [];
+
+        return fx;
+      })
+      .routeAction(fx => {
+        fx.data = testAction;
+
+        fx.included.push(testProgramAction);
+
+        return fx;
+      })
+      .routeActionFiles(fx => {
+        fx.data = [];
+
+        return fx;
+      })
+      .visit(`/patient/${ testPatient.id }/action/${ testAction.id }`)
+      .wait('@routePatientActions')
+      .wait('@routePatientFlows')
+      .wait('@routeAction')
+      .wait('@routeActionFiles');
+
+    cy
+      .get('.patient__list')
+      .find('.table-list__item .fa-paperclip')
+      .should('not.exist');
+
+
+    const putFileURL = '/api/actions/**/relationships/files?urls=upload';
+
+    let fileId;
+
+    cy
+      .intercept('PUT', putFileURL, req => {
+        expect(req.body.data.attributes.path).to.include('test.pdf');
+        fileId = req.body.data.id;
+        req.reply({
+          statusCode: 201,
+          body: {
+            data: {
+              id: fileId,
+              attributes: {
+                path: req.body.data.attributes.path,
+                created_at: testTs(),
+              },
+              meta: {
+                upload: '/upload-test',
+              },
+            },
+          },
+        });
+      }).as('routePutFile');
+
+    cy
+      .intercept('PUT', '/upload-test', req => {
+        req.reply({
+          statusCode: 200,
+          throttleKbps: 10,
+        });
+      }).as('routeUploadFile');
+
+    cy
+      .intercept('GET', '/api/files/*', req => {
+        req.reply({
+          statusCode: 200,
+          body: {
+            data: {
+              id: fileId,
+              attributes: {
+                path: '/dir/test.pdf',
+                created_at: testTs(),
+              },
+              meta: {
+                download: '/download-test',
+                view: '/view-test',
+              },
+            },
+          },
+        });
+      }).as('routeGetFile');
+
+    cy
+      .intercept('DELETE', '/api/files/*', {
+        statusCode: 204,
+        body: {},
+      })
+      .as('routeDeleteFile');
+
+    cy
+      .get('#upload-attachment')
+      .selectFile({
+        contents: Cypress.Buffer.from('test'),
+        fileName: 'test.pdf',
+      }, { force: true });
+
+    cy
+      .get('.patient__list')
+      .find('.table-list__item .fa-paperclip')
+      .should('exist');
+
+    cy
+      .get('.sidebar')
+      .find('[data-attachments-files-region]')
+      .first()
+      .contains('Remove')
+      .click();
+
+    cy
+      .get('.modal--small')
+      .find('.js-submit')
+      .click()
+      .wait('@routeDeleteFile');
+
+    cy
+      .get('.patient__list')
+      .find('.table-list__item .fa-paperclip')
+      .should('not.exist');
+  });
+
   specify('action attachments - uploads not allowed on program action', function() {
     const testProgramAction = getProgramAction({
       attributes: {