diff --git a/crates/cli/src/lib.rs b/crates/cli/src/lib.rs
index 208d1541e..7bb8cfc13 100644
--- a/crates/cli/src/lib.rs
+++ b/crates/cli/src/lib.rs
@@ -9,6 +9,7 @@ mod native_operations;
 use std::path::PathBuf;
 
 use clap::Subcommand;
+use metadata::NativeToolchainDefinition;
 use tokio::fs;
 
 use ndc_postgres_configuration as configuration;
@@ -134,6 +135,18 @@ async fn initialize(with_metadata: bool, context: Context<impl Environment>) ->
                 action: metadata::DockerComposeWatchAction::SyncAndRestart,
                 ignore: vec![],
             }],
+            native_toolchain_definition: Some(NativeToolchainDefinition {
+                commands: vec![
+                    ("start".to_string(), metadata::CommandDefinition::ShellScript {
+                        bash: "#!/usr/bin/env bash\nset -eu -o pipefail\nHASURA_CONFIGURATION_DIRECTORY=\"$HASURA_PLUGIN_CONNECTOR_CONTEXT_PATH\" \"$HASURA_DDN_NATIVE_CONNECTOR_DIR/ndc-postgres\" serve".to_string(),
+                        powershell: "$ErrorActionPreference = \"Stop\"\n$env:HASURA_CONFIGURATION_DIRECTORY=\"$env:HASURA_PLUGIN_CONNECTOR_CONTEXT_PATH\"; & \"$env:HASURA_DDN_NATIVE_CONNECTOR_DIR\\ndc-postgres.exe\" serve".to_string(),
+                    }),
+                    ("update".to_string(), metadata::CommandDefinition::ShellScript {
+                        bash: "#!/usr/bin/env bash\nset -eu -o pipefail\n\"$HASURA_DDN_NATIVE_CONNECTOR_PLUGIN_DIR/hasura-ndc-postgres\" update".to_string(),
+                        powershell: "$ErrorActionPreference = \"Stop\"\n& \"$env:HASURA_DDN_NATIVE_CONNECTOR_PLUGIN_DIR\\hasura-ndc-postgres.exe\" update".to_string(),
+                    }),
+                ].into_iter().collect(),
+            })
         };
 
         fs::write(metadata_file, serde_yaml::to_string(&metadata)?).await?;
diff --git a/crates/cli/src/metadata.rs b/crates/cli/src/metadata.rs
index 74d2c8d1c..756df3ff7 100644
--- a/crates/cli/src/metadata.rs
+++ b/crates/cli/src/metadata.rs
@@ -2,6 +2,8 @@
 //!
 //! See https://github.com/hasura/ndc-hub/blob/main/rfcs/0001-packaging.md#connector-definition.
 
+use std::collections::BTreeMap;
+
 use serde::{Deserialize, Serialize};
 
 #[derive(Debug, Serialize, Deserialize)]
@@ -14,6 +16,8 @@ pub struct ConnectorMetadataDefinition {
     pub cli_plugin: Option<CliPluginDefinition>,
     #[serde(skip_serializing_if = "Vec::is_empty")]
     pub docker_compose_watch: DockerComposeWatch,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub native_toolchain_definition: Option<NativeToolchainDefinition>,
 }
 
 #[derive(Debug, Serialize, Deserialize)]
@@ -75,3 +79,23 @@ pub enum DockerComposeWatchAction {
     #[serde(rename = "sync+restart")]
     SyncAndRestart,
 }
+
+#[derive(Debug, Serialize, Deserialize)]
+#[serde(rename_all = "camelCase")]
+pub struct NativeToolchainDefinition {
+    pub commands: BTreeMap<CommandName, CommandDefinition>,
+}
+
+pub type CommandName = String;
+
+#[derive(Debug, Serialize, Deserialize)]
+#[serde(rename_all = "PascalCase", tag = "type")]
+pub enum CommandDefinition {
+    #[serde(rename_all = "camelCase")]
+    ShellScript { bash: String, powershell: String },
+    #[serde(rename_all = "camelCase")]
+    DockerizedCommand {
+        docker_image: String,
+        command_args: Vec<String>,
+    },
+}
diff --git a/crates/cli/tests/snapshots/initialize_tests__initialize_directory_with_metadata.snap b/crates/cli/tests/snapshots/initialize_tests__initialize_directory_with_metadata.snap
index 1dc499fea..78d7bd254 100644
--- a/crates/cli/tests/snapshots/initialize_tests__initialize_directory_with_metadata.snap
+++ b/crates/cli/tests/snapshots/initialize_tests__initialize_directory_with_metadata.snap
@@ -27,3 +27,23 @@ dockerComposeWatch:
 - path: ./
   target: /etc/connector
   action: sync+restart
+nativeToolchainDefinition:
+  commands:
+    start:
+      type: ShellScript
+      bash: |-
+        #!/usr/bin/env bash
+        set -eu -o pipefail
+        HASURA_CONFIGURATION_DIRECTORY="$HASURA_PLUGIN_CONNECTOR_CONTEXT_PATH" "$HASURA_DDN_NATIVE_CONNECTOR_DIR/ndc-postgres" serve
+      powershell: |-
+        $ErrorActionPreference = "Stop"
+        $env:HASURA_CONFIGURATION_DIRECTORY="$env:HASURA_PLUGIN_CONNECTOR_CONTEXT_PATH"; & "$env:HASURA_DDN_NATIVE_CONNECTOR_DIR\ndc-postgres.exe" serve
+    update:
+      type: ShellScript
+      bash: |-
+        #!/usr/bin/env bash
+        set -eu -o pipefail
+        "$HASURA_DDN_NATIVE_CONNECTOR_PLUGIN_DIR/hasura-ndc-postgres" update
+      powershell: |-
+        $ErrorActionPreference = "Stop"
+        & "$env:HASURA_DDN_NATIVE_CONNECTOR_PLUGIN_DIR\hasura-ndc-postgres.exe" update
diff --git a/crates/cli/tests/snapshots/initialize_tests__initialize_directory_with_metadata_and_release_version.snap b/crates/cli/tests/snapshots/initialize_tests__initialize_directory_with_metadata_and_release_version.snap
index 1ee975a94..1420b3ebf 100644
--- a/crates/cli/tests/snapshots/initialize_tests__initialize_directory_with_metadata_and_release_version.snap
+++ b/crates/cli/tests/snapshots/initialize_tests__initialize_directory_with_metadata_and_release_version.snap
@@ -27,3 +27,23 @@ dockerComposeWatch:
 - path: ./
   target: /etc/connector
   action: sync+restart
+nativeToolchainDefinition:
+  commands:
+    start:
+      type: ShellScript
+      bash: |-
+        #!/usr/bin/env bash
+        set -eu -o pipefail
+        HASURA_CONFIGURATION_DIRECTORY="$HASURA_PLUGIN_CONNECTOR_CONTEXT_PATH" "$HASURA_DDN_NATIVE_CONNECTOR_DIR/ndc-postgres" serve
+      powershell: |-
+        $ErrorActionPreference = "Stop"
+        $env:HASURA_CONFIGURATION_DIRECTORY="$env:HASURA_PLUGIN_CONNECTOR_CONTEXT_PATH"; & "$env:HASURA_DDN_NATIVE_CONNECTOR_DIR\ndc-postgres.exe" serve
+    update:
+      type: ShellScript
+      bash: |-
+        #!/usr/bin/env bash
+        set -eu -o pipefail
+        "$HASURA_DDN_NATIVE_CONNECTOR_PLUGIN_DIR/hasura-ndc-postgres" update
+      powershell: |-
+        $ErrorActionPreference = "Stop"
+        & "$env:HASURA_DDN_NATIVE_CONNECTOR_PLUGIN_DIR\hasura-ndc-postgres.exe" update