diff --git a/isideload/src/dev/app_groups.rs b/isideload/src/dev/app_groups.rs
index 881153b..c17d2a9 100644
--- a/isideload/src/dev/app_groups.rs
+++ b/isideload/src/dev/app_groups.rs
@@ -7,6 +7,7 @@ use crate::dev::{
 use plist_macro::plist;
 use rootcause::prelude::*;
 use serde::Deserialize;
+use tracing::info;
 
 #[derive(Debug, Clone, Deserialize)]
 #[serde(rename_all = "camelCase")]
@@ -91,6 +92,28 @@ pub trait AppGroupsApi {
 
         Ok(())
     }
+
+    async fn ensure_app_group(
+        &mut self,
+        team: &DeveloperTeam,
+        name: &str,
+        identifier: &str,
+        device_type: impl Into<Option<DeveloperDeviceType>> + Send,
+    ) -> Result<AppGroup, Report> {
+        let device_type = device_type.into();
+        let groups = self.list_app_groups(team, device_type.clone()).await?;
+        let matching_group = groups.iter().find(|g| g.identifier == identifier);
+
+        if let Some(group) = matching_group {
+            Ok(group.clone())
+        } else {
+            info!("Adding application group");
+            let group = self
+                .add_app_group(team, name, identifier, device_type)
+                .await?;
+            Ok(group)
+        }
+    }
 }
 
 impl AppGroupsApi for DeveloperSession {
diff --git a/isideload/src/sideload/sideloader.rs b/isideload/src/sideload/sideloader.rs
index a56ba39..f8e808e 100644
--- a/isideload/src/sideload/sideloader.rs
+++ b/isideload/src/sideload/sideloader.rs
@@ -1,5 +1,7 @@
 use crate::{
     dev::{
+        app_groups::AppGroupsApi,
+        app_ids::AppIdsApi,
         developer_session::DeveloperSession,
         devices::DevicesApi,
         teams::{DeveloperTeam, TeamsApi},
@@ -98,15 +100,8 @@ impl Sideloader {
                     main_app_id_str
                 );
             }
-        };
-
-        for app_id in app_ids.iter_mut() {
-            app_id
-                .ensure_group_feature(&mut self.dev_session, &team)
-                .await?;
-
-            // TODO: Increased memory entitlement
         }
+        .clone();
 
         let group_identifier = format!(
             "group.{}",
@@ -117,6 +112,28 @@ impl Sideloader {
             }
         );
 
+        let app_group = self
+            .dev_session
+            .ensure_app_group(&team, &main_app_name, &group_identifier, None)
+            .await?;
+
+        for app_id in app_ids.iter_mut() {
+            app_id
+                .ensure_group_feature(&mut self.dev_session, &team)
+                .await?;
+
+            self.dev_session
+                .assign_app_group(&team, &app_group, app_id, None)
+                .await?;
+
+            // TODO: Increased memory entitlement
+        }
+
+        let provisioning_profile = self
+            .dev_session
+            .download_team_provisioning_profile(&team, &main_app_id, None)
+            .await?;
+
         Ok(())
     }