diff --git a/crates/collab/src/api/billing.rs b/crates/collab/src/api/billing.rs
index dca5a772f45d81..838dea19819194 100644
--- a/crates/collab/src/api/billing.rs
+++ b/crates/collab/src/api/billing.rs
@@ -197,10 +197,10 @@ async fn create_billing_subscription(
         .await?
         .ok_or_else(|| anyhow!("user not found"))?;
 
-    let Some((stripe_client, stripe_price_id)) = app
+    let Some((stripe_client, stripe_access_price_id)) = app
         .stripe_client
         .clone()
-        .zip(app.config.stripe_llm_usage_price_id.clone())
+        .zip(app.config.stripe_llm_access_price_id.clone())
     else {
         log::error!("failed to retrieve Stripe client or price ID");
         Err(Error::http(
@@ -232,8 +232,8 @@ async fn create_billing_subscription(
         params.customer = Some(customer_id);
         params.client_reference_id = Some(user.github_login.as_str());
         params.line_items = Some(vec![CreateCheckoutSessionLineItems {
-            price: Some(stripe_price_id.to_string()),
-            quantity: Some(0),
+            price: Some(stripe_access_price_id.to_string()),
+            quantity: Some(1),
             ..Default::default()
         }]);
         let success_url = format!("{}/account", app.config.zed_dot_dev_url());
@@ -787,22 +787,33 @@ async fn update_stripe_subscription(
         monthly_spending.saturating_sub(FREE_TIER_MONTHLY_SPENDING_LIMIT);
 
     let new_quantity = (monthly_spending_over_free_tier.0 as f32 / 100.).ceil();
-    Subscription::update(
-        stripe_client,
-        &subscription_id,
-        stripe::UpdateSubscription {
-            items: Some(vec![stripe::UpdateSubscriptionItems {
-                // TODO: Do we need to send up the `id` if a subscription item
-                // with this price already exists, or will Stripe take care of
-                // it?
-                id: None,
-                price: Some(stripe_llm_usage_price_id.to_string()),
-                quantity: Some(new_quantity as u64),
-                ..Default::default()
-            }]),
+    let current_subscription = Subscription::retrieve(stripe_client, &subscription_id, &[]).await?;
+
+    let mut update_params = stripe::UpdateSubscription {
+        proration_behavior: Some(
+            stripe::generated::billing::subscription::SubscriptionProrationBehavior::None,
+        ),
+        ..Default::default()
+    };
+
+    if let Some(existing_item) = current_subscription.items.data.iter().find(|item| {
+        item.price.as_ref().map_or(false, |price| {
+            price.id == stripe_llm_usage_price_id.as_ref()
+        })
+    }) {
+        update_params.items = Some(vec![stripe::UpdateSubscriptionItems {
+            id: Some(existing_item.id.to_string()),
+            quantity: Some(new_quantity as u64),
             ..Default::default()
-        },
-    )
-    .await?;
+        }]);
+    } else {
+        update_params.items = Some(vec![stripe::UpdateSubscriptionItems {
+            price: Some(stripe_llm_usage_price_id.to_string()),
+            quantity: Some(new_quantity as u64),
+            ..Default::default()
+        }]);
+    }
+
+    Subscription::update(stripe_client, &subscription_id, update_params).await?;
     Ok(())
 }
diff --git a/crates/collab/src/lib.rs b/crates/collab/src/lib.rs
index a6141abb888730..3896926f4372fe 100644
--- a/crates/collab/src/lib.rs
+++ b/crates/collab/src/lib.rs
@@ -176,6 +176,7 @@ pub struct Config {
     pub slack_panics_webhook: Option<String>,
     pub auto_join_channel_id: Option<ChannelId>,
     pub stripe_api_key: Option<String>,
+    pub stripe_llm_access_price_id: Option<Arc<str>>,
     pub stripe_llm_usage_price_id: Option<Arc<str>>,
     pub supermaven_admin_api_key: Option<Arc<str>>,
     pub user_backfiller_github_access_token: Option<Arc<str>>,
@@ -237,6 +238,7 @@ impl Config {
             migrations_path: None,
             seed_path: None,
             stripe_api_key: None,
+            stripe_llm_access_price_id: None,
             stripe_llm_usage_price_id: None,
             supermaven_admin_api_key: None,
             user_backfiller_github_access_token: None,
diff --git a/crates/collab/src/main.rs b/crates/collab/src/main.rs
index bbbd4e562cb901..bd227f17c70404 100644
--- a/crates/collab/src/main.rs
+++ b/crates/collab/src/main.rs
@@ -155,7 +155,8 @@ async fn main() -> Result<()> {
                     .await
                     .trace_err();
 
-                    if let Some(llm_db) = llm_db {
+                    if let Some(mut llm_db) = llm_db {
+                        llm_db.initialize().await?;
                         sync_llm_usage_with_stripe_periodically(state.clone(), llm_db);
                     }
 
diff --git a/crates/collab/src/tests/test_server.rs b/crates/collab/src/tests/test_server.rs
index 55bc279c8eaf6e..683a53a2f56618 100644
--- a/crates/collab/src/tests/test_server.rs
+++ b/crates/collab/src/tests/test_server.rs
@@ -677,6 +677,7 @@ impl TestServer {
                 migrations_path: None,
                 seed_path: None,
                 stripe_api_key: None,
+                stripe_llm_access_price_id: None,
                 stripe_llm_usage_price_id: None,
                 supermaven_admin_api_key: None,
                 user_backfiller_github_access_token: None,