diff --git a/Cargo.lock b/Cargo.lock
index c9bd051aeb..a8baa9788b 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -834,6 +834,26 @@ dependencies = [
  "syn 2.0.59",
 ]
 
+[[package]]
+name = "async-stripe"
+version = "0.37.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "e2f14b5943a52cf051bbbbb68538e93a69d1e291934174121e769f4b181113f5"
+dependencies = [
+ "futures-util",
+ "http-types",
+ "hyper",
+ "hyper-rustls",
+ "serde",
+ "serde_json",
+ "serde_path_to_error",
+ "serde_qs 0.10.1",
+ "smart-default",
+ "smol_str",
+ "thiserror",
+ "tokio",
+]
+
 [[package]]
 name = "async-tar"
 version = "0.4.2"
@@ -1462,6 +1482,12 @@ version = "0.1.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "349a06037c7bf932dd7e7d1f653678b2038b9ad46a74102f1fc7bd7872678cce"
 
+[[package]]
+name = "base64"
+version = "0.13.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "9e1b586273c5702936fe7b7d6896644d8be71e6314cfe09d3167c95f712589e8"
+
 [[package]]
 name = "base64"
 version = "0.21.7"
@@ -2425,6 +2451,7 @@ dependencies = [
  "anthropic",
  "anyhow",
  "assistant",
+ "async-stripe",
  "async-trait",
  "async-tungstenite",
  "audio",
@@ -5254,6 +5281,27 @@ version = "0.3.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "add0ab9360ddbd88cfeb3bd9574a1d85cfdfa14db10b3e21d3700dbc4328758f"
 
+[[package]]
+name = "http-types"
+version = "2.12.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "6e9b187a72d63adbfba487f48095306ac823049cb504ee195541e91c7775f5ad"
+dependencies = [
+ "anyhow",
+ "async-channel 1.9.0",
+ "base64 0.13.1",
+ "futures-lite 1.13.0",
+ "http 0.2.9",
+ "infer",
+ "pin-project-lite",
+ "rand 0.7.3",
+ "serde",
+ "serde_json",
+ "serde_qs 0.8.5",
+ "serde_urlencoded",
+ "url",
+]
+
 [[package]]
 name = "http_client"
 version = "0.1.0"
@@ -5512,6 +5560,12 @@ version = "2.0.5"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "b248f5224d1d606005e02c97f5aa4e88eeb230488bcc03bc9ca4d7991399f2b5"
 
+[[package]]
+name = "infer"
+version = "0.2.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "64e9829a50b42bb782c1df523f78d332fe371b10c661e78b7a3c34b0198e9fac"
+
 [[package]]
 name = "inherent"
 version = "1.0.10"
@@ -9564,6 +9618,28 @@ dependencies = [
  "serde",
 ]
 
+[[package]]
+name = "serde_qs"
+version = "0.8.5"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "c7715380eec75f029a4ef7de39a9200e0a63823176b759d055b613f5a87df6a6"
+dependencies = [
+ "percent-encoding",
+ "serde",
+ "thiserror",
+]
+
+[[package]]
+name = "serde_qs"
+version = "0.10.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "8cac3f1e2ca2fe333923a1ae72caca910b98ed0630bb35ef6f8c8517d6e81afa"
+dependencies = [
+ "percent-encoding",
+ "serde",
+ "thiserror",
+]
+
 [[package]]
 name = "serde_repr"
 version = "0.1.16"
@@ -9880,6 +9956,17 @@ dependencies = [
  "serde",
 ]
 
+[[package]]
+name = "smart-default"
+version = "0.6.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "133659a15339456eeeb07572eb02a91c91e9815e9cbc89566944d2c8d3efdbf6"
+dependencies = [
+ "proc-macro2",
+ "quote",
+ "syn 1.0.109",
+]
+
 [[package]]
 name = "smol"
 version = "1.3.0"
@@ -9897,6 +9984,15 @@ dependencies = [
  "futures-lite 1.13.0",
 ]
 
+[[package]]
+name = "smol_str"
+version = "0.1.24"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "fad6c857cbab2627dcf01ec85a623ca4e7dcb5691cbaa3d7fb7653671f0d09c9"
+dependencies = [
+ "serde",
+]
+
 [[package]]
 name = "snippet"
 version = "0.1.0"
diff --git a/Cargo.toml b/Cargo.toml
index 5c407ed0ef..a5be5bc027 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -309,6 +309,7 @@ async-dispatcher = "0.1"
 async-fs = "1.6"
 async-pipe = { git = "https://github.com/zed-industries/async-pipe-rs", rev = "82d00a04211cf4e1236029aa03e6b6ce2a74c553" }
 async-recursion = "1.0.0"
+async-stripe = { version = "0.37", default-features = false, features = ["runtime-tokio-hyper-rustls", "billing", "checkout"] }
 async-tar = "0.4.2"
 async-trait = "0.1"
 async-tungstenite = "0.23"
diff --git a/crates/collab/Cargo.toml b/crates/collab/Cargo.toml
index b321c4b95f..289212a6b1 100644
--- a/crates/collab/Cargo.toml
+++ b/crates/collab/Cargo.toml
@@ -20,6 +20,7 @@ test-support = ["sqlite"]
 [dependencies]
 anthropic.workspace = true
 anyhow.workspace = true
+async-stripe.workspace = true
 async-tungstenite.workspace = true
 aws-config = { version = "1.1.5" }
 aws-sdk-s3 = { version = "1.15.0" }
@@ -116,3 +117,6 @@ util.workspace = true
 workspace = { workspace = true, features = ["test-support"] }
 worktree = { workspace = true, features = ["test-support"] }
 headless.workspace = true
+
+[package.metadata.cargo-machete]
+ignored = ["async-stripe"]
diff --git a/crates/collab/src/api.rs b/crates/collab/src/api.rs
index f5902114a1..35db23d58d 100644
--- a/crates/collab/src/api.rs
+++ b/crates/collab/src/api.rs
@@ -1,3 +1,4 @@
+pub mod billing;
 pub mod contributors;
 pub mod events;
 pub mod extensions;
@@ -31,6 +32,7 @@ pub fn routes(rpc_server: Option<Arc<rpc::Server>>, state: Arc<AppState>) -> Rou
         .route("/user", get(get_authenticated_user))
         .route("/users/:id/access_tokens", post(create_access_token))
         .route("/rpc_server_snapshot", get(get_rpc_server_snapshot))
+        .merge(billing::router())
         .merge(contributors::router())
         .layer(
             ServiceBuilder::new()
diff --git a/crates/collab/src/api/billing.rs b/crates/collab/src/api/billing.rs
new file mode 100644
index 0000000000..c454f4884b
--- /dev/null
+++ b/crates/collab/src/api/billing.rs
@@ -0,0 +1,88 @@
+use std::str::FromStr;
+use std::sync::Arc;
+
+use anyhow::anyhow;
+use axum::{extract, routing::post, Extension, Json, Router};
+use collections::HashSet;
+use reqwest::StatusCode;
+use serde::{Deserialize, Serialize};
+use stripe::{CheckoutSession, CreateCheckoutSession, CreateCheckoutSessionLineItems, CustomerId};
+
+use crate::{AppState, Error, Result};
+
+pub fn router() -> Router {
+    Router::new().route("/billing/subscriptions", post(create_billing_subscription))
+}
+
+#[derive(Debug, Deserialize)]
+struct CreateBillingSubscriptionBody {
+    github_user_id: i32,
+}
+
+#[derive(Debug, Serialize)]
+struct CreateBillingSubscriptionResponse {
+    checkout_session_url: String,
+}
+
+/// Initiates a Stripe Checkout session for creating a billing subscription.
+async fn create_billing_subscription(
+    Extension(app): Extension<Arc<AppState>>,
+    extract::Json(body): extract::Json<CreateBillingSubscriptionBody>,
+) -> Result<Json<CreateBillingSubscriptionResponse>> {
+    let user = app
+        .db
+        .get_user_by_github_user_id(body.github_user_id)
+        .await?
+        .ok_or_else(|| anyhow!("user not found"))?;
+
+    let Some((stripe_client, stripe_price_id)) = app
+        .stripe_client
+        .clone()
+        .zip(app.config.stripe_price_id.clone())
+    else {
+        log::error!("failed to retrieve Stripe client or price ID");
+        Err(Error::Http(
+            StatusCode::NOT_IMPLEMENTED,
+            "not supported".into(),
+        ))?
+    };
+
+    let existing_customer_id = {
+        let existing_subscriptions = app.db.get_billing_subscriptions(user.id).await?;
+        let distinct_customer_ids = existing_subscriptions
+            .iter()
+            .map(|subscription| subscription.stripe_customer_id.as_str())
+            .collect::<HashSet<_>>();
+        // Sanity: Make sure we can determine a single Stripe customer ID for the user.
+        if distinct_customer_ids.len() > 1 {
+            Err(anyhow!("user has multiple existing customer IDs"))?;
+        }
+
+        distinct_customer_ids
+            .into_iter()
+            .next()
+            .map(|id| CustomerId::from_str(id).map_err(|err| anyhow!(err)))
+            .transpose()
+    }?;
+
+    let checkout_session = {
+        let mut params = CreateCheckoutSession::new();
+        params.mode = Some(stripe::CheckoutSessionMode::Subscription);
+        params.customer = existing_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(1),
+            ..Default::default()
+        }]);
+        params.success_url = Some("https://zed.dev/billing/success");
+
+        CheckoutSession::create(&stripe_client, params).await?
+    };
+
+    Ok(Json(CreateBillingSubscriptionResponse {
+        checkout_session_url: checkout_session
+            .url
+            .ok_or_else(|| anyhow!("no checkout session URL"))?,
+    }))
+}
diff --git a/crates/collab/src/db/queries/billing_subscriptions.rs b/crates/collab/src/db/queries/billing_subscriptions.rs
index ce782e5eb3..fcacf7ee22 100644
--- a/crates/collab/src/db/queries/billing_subscriptions.rs
+++ b/crates/collab/src/db/queries/billing_subscriptions.rs
@@ -32,6 +32,26 @@ impl Database {
         .await
     }
 
+    /// Returns all of the billing subscriptions for the user with the specified ID.
+    ///
+    /// Note that this returns the subscriptions regardless of their status.
+    /// If you're wanting to check if a use has an active billing subscription,
+    /// use `get_active_billing_subscriptions` instead.
+    pub async fn get_billing_subscriptions(
+        &self,
+        user_id: UserId,
+    ) -> Result<Vec<billing_subscription::Model>> {
+        self.transaction(|tx| async move {
+            let subscriptions = billing_subscription::Entity::find()
+                .filter(billing_subscription::Column::UserId.eq(user_id))
+                .all(&*tx)
+                .await?;
+
+            Ok(subscriptions)
+        })
+        .await
+    }
+
     /// Returns all of the active billing subscriptions for the user with the specified ID.
     pub async fn get_active_billing_subscriptions(
         &self,
diff --git a/crates/collab/src/db/queries/users.rs b/crates/collab/src/db/queries/users.rs
index ff5c4d5c17..fde6aa0b12 100644
--- a/crates/collab/src/db/queries/users.rs
+++ b/crates/collab/src/db/queries/users.rs
@@ -61,6 +61,17 @@ impl Database {
         .await
     }
 
+    /// Returns a user by GitHub user ID. There are no access checks here, so this should only be used internally.
+    pub async fn get_user_by_github_user_id(&self, github_user_id: i32) -> Result<Option<User>> {
+        self.transaction(|tx| async move {
+            Ok(user::Entity::find()
+                .filter(user::Column::GithubUserId.eq(github_user_id))
+                .one(&*tx)
+                .await?)
+        })
+        .await
+    }
+
     /// Returns a user by GitHub login. There are no access checks here, so this should only be used internally.
     pub async fn get_user_by_github_login(&self, github_login: &str) -> Result<Option<User>> {
         self.transaction(|tx| async move {
diff --git a/crates/collab/src/lib.rs b/crates/collab/src/lib.rs
index 2673ca3fb8..89705428aa 100644
--- a/crates/collab/src/lib.rs
+++ b/crates/collab/src/lib.rs
@@ -26,6 +26,7 @@ pub enum Error {
     Http(StatusCode, String),
     Database(sea_orm::error::DbErr),
     Internal(anyhow::Error),
+    Stripe(stripe::StripeError),
 }
 
 impl From<anyhow::Error> for Error {
@@ -40,6 +41,12 @@ impl From<sea_orm::error::DbErr> for Error {
     }
 }
 
+impl From<stripe::StripeError> for Error {
+    fn from(error: stripe::StripeError) -> Self {
+        Self::Stripe(error)
+    }
+}
+
 impl From<axum::Error> for Error {
     fn from(error: axum::Error) -> Self {
         Self::Internal(error.into())
@@ -81,6 +88,14 @@ impl IntoResponse for Error {
                 );
                 (StatusCode::INTERNAL_SERVER_ERROR, format!("{}", &error)).into_response()
             }
+            Error::Stripe(error) => {
+                log::error!(
+                    "HTTP error {}: {:?}",
+                    StatusCode::INTERNAL_SERVER_ERROR,
+                    &error
+                );
+                (StatusCode::INTERNAL_SERVER_ERROR, format!("{}", &error)).into_response()
+            }
         }
     }
 }
@@ -91,6 +106,7 @@ impl std::fmt::Debug for Error {
             Error::Http(code, message) => (code, message).fmt(f),
             Error::Database(error) => error.fmt(f),
             Error::Internal(error) => error.fmt(f),
+            Error::Stripe(error) => error.fmt(f),
         }
     }
 }
@@ -101,6 +117,7 @@ impl std::fmt::Display for Error {
             Error::Http(code, message) => write!(f, "{code}: {message}"),
             Error::Database(error) => error.fmt(f),
             Error::Internal(error) => error.fmt(f),
+            Error::Stripe(error) => error.fmt(f),
         }
     }
 }
@@ -137,6 +154,8 @@ pub struct Config {
     pub zed_client_checksum_seed: Option<String>,
     pub slack_panics_webhook: Option<String>,
     pub auto_join_channel_id: Option<ChannelId>,
+    pub stripe_api_key: Option<String>,
+    pub stripe_price_id: Option<Arc<str>>,
     pub supermaven_admin_api_key: Option<Arc<str>>,
 }
 
@@ -150,6 +169,7 @@ pub struct AppState {
     pub db: Arc<Database>,
     pub live_kit_client: Option<Arc<dyn live_kit_server::api::Client>>,
     pub blob_store_client: Option<aws_sdk_s3::Client>,
+    pub stripe_client: Option<Arc<stripe::Client>>,
     pub rate_limiter: Arc<RateLimiter>,
     pub executor: Executor,
     pub clickhouse_client: Option<clickhouse::Client>,
@@ -183,6 +203,10 @@ impl AppState {
             db: db.clone(),
             live_kit_client,
             blob_store_client: build_blob_store_client(&config).await.log_err(),
+            stripe_client: build_stripe_client(&config)
+                .await
+                .map(|client| Arc::new(client))
+                .log_err(),
             rate_limiter: Arc::new(RateLimiter::new(db)),
             executor,
             clickhouse_client: config
@@ -195,6 +219,15 @@ impl AppState {
     }
 }
 
+async fn build_stripe_client(config: &Config) -> anyhow::Result<stripe::Client> {
+    let api_key = config
+        .stripe_api_key
+        .as_ref()
+        .ok_or_else(|| anyhow!("missing stripe_api_key"))?;
+
+    Ok(stripe::Client::new(api_key))
+}
+
 async fn build_blob_store_client(config: &Config) -> anyhow::Result<aws_sdk_s3::Client> {
     let keys = aws_sdk_s3::config::Credentials::new(
         config
diff --git a/crates/collab/src/tests/test_server.rs b/crates/collab/src/tests/test_server.rs
index dea29b697f..7a3bc92a5f 100644
--- a/crates/collab/src/tests/test_server.rs
+++ b/crates/collab/src/tests/test_server.rs
@@ -637,6 +637,7 @@ impl TestServer {
             db: test_db.db().clone(),
             live_kit_client: Some(Arc::new(live_kit_test_server.create_api_client())),
             blob_store_client: None,
+            stripe_client: None,
             rate_limiter: Arc::new(RateLimiter::new(test_db.db().clone())),
             executor,
             clickhouse_client: None,
@@ -669,6 +670,8 @@ impl TestServer {
                 auto_join_channel_id: None,
                 migrations_path: None,
                 seed_path: None,
+                stripe_api_key: None,
+                stripe_price_id: None,
                 supermaven_admin_api_key: None,
             },
         })