diff --git a/linkup-cli/src/check.rs b/linkup-cli/src/check.rs
index 55f4c3a..13eb34d 100644
--- a/linkup-cli/src/check.rs
+++ b/linkup-cli/src/check.rs
@@ -1,6 +1,6 @@
 use std::fs::{self, OpenOptions};
 use std::io::Write;
-use std::path::Path;
+use std::path::{Path, PathBuf};
 
 use reqwest::blocking::Client;
 use reqwest::StatusCode;
@@ -30,7 +30,7 @@ pub fn check() -> Result<(), CliError> {
 
     for service in &state.services {
         match &service.directory {
-            Some(d) => set_service_env(d.clone())?,
+            Some(d) => set_service_env(d.clone(), state.linkup.config_path.clone())?,
             None => {}
         }
     }
@@ -140,9 +140,16 @@ fn server_config_from_state(state: &LocalState) -> (StorableSession, StorableSes
     )
 }
 
-fn set_service_env(directory: String) -> Result<(), CliError> {
-    let dev_env_path = format!("{}/.env.dev", directory);
-    let env_path = format!("{}/.env", directory);
+fn set_service_env(directory: String, config_path: String) -> Result<(), CliError> {
+    let config_dir = Path::new(&config_path).parent().ok_or_else(|| {
+        CliError::SetServiceEnv(
+            directory.clone(),
+            "config_path does not have a parent directory".to_string(),
+        )
+    })?;
+
+    let dev_env_path = PathBuf::from(config_dir).join(&directory).join(".env.dev");
+    let env_path = PathBuf::from(config_dir).join(&directory).join(".env");
 
     if !Path::new(&dev_env_path).exists() {
         return Err(CliError::NoDevEnv(directory));
@@ -155,6 +162,12 @@ fn set_service_env(directory: String) -> Result<(), CliError> {
         )
     })?;
 
+    if let Ok(env_content) = fs::read_to_string(&env_path) {
+        if env_content.contains(LINKUP_ENV_SEPARATOR) {
+            return Ok(());
+        }
+    }
+
     let mut env_file = OpenOptions::new()
         .create(true)
         .append(true)
diff --git a/linkup-cli/src/local_config.rs b/linkup-cli/src/local_config.rs
index d970107..ad625a1 100644
--- a/linkup-cli/src/local_config.rs
+++ b/linkup-cli/src/local_config.rs
@@ -17,6 +17,7 @@ pub struct LocalState {
 pub struct LinkupState {
     pub session_name: String,
     pub session_token: String,
+    pub config_path: String,
     pub remote: Url,
     pub tunnel: Url,
 }
@@ -67,7 +68,7 @@ struct YamlLocalService {
     rewrites: Option<Vec<StorableRewrite>>,
 }
 
-pub fn config_to_state(yaml_config: YamlLocalConfig) -> LocalState {
+pub fn config_to_state(yaml_config: YamlLocalConfig, config_path: String) -> LocalState {
     let random_token: String = rand::thread_rng()
         .sample_iter(&Alphanumeric)
         .take(16)
@@ -77,6 +78,7 @@ pub fn config_to_state(yaml_config: YamlLocalConfig) -> LocalState {
     let linkup = LinkupState {
         session_name: String::new(),
         session_token: random_token,
+        config_path,
         remote: yaml_config.linkup.remote,
         tunnel: Url::parse("http://localhost").expect("default url parses"),
     };
@@ -143,7 +145,9 @@ domains:
     fn test_config_to_state() {
         let input_str = String::from(CONF_STR);
         let yaml_config = serde_yaml::from_str(&input_str).unwrap();
-        let local_state = config_to_state(yaml_config);
+        let local_state = config_to_state(yaml_config, "./path/to/config.yaml".to_string());
+
+        assert_eq!(local_state.linkup.config_path, "./path/to/config.yaml");
 
         assert_eq!(
             local_state.linkup.remote,
diff --git a/linkup-cli/src/start.rs b/linkup-cli/src/start.rs
index 5e615ff..41b7c9e 100644
--- a/linkup-cli/src/start.rs
+++ b/linkup-cli/src/start.rs
@@ -14,9 +14,10 @@ pub fn start(config_arg: Option<String>) -> Result<(), CliError> {
     // TODO: run `stop` to kill the previous local server?
 
     let previous_state = get_state();
-    let input_config = get_config(config_arg)?;
+    let config_path = config_path(config_arg)?;
+    let input_config = get_config(config_path.clone())?;
 
-    let mut state = config_to_state(input_config);
+    let mut state = config_to_state(input_config, config_path);
 
     // Reuse previous session name if possible
     if let Ok(ps) = previous_state {
@@ -31,19 +32,20 @@ pub fn start(config_arg: Option<String>) -> Result<(), CliError> {
     Ok(())
 }
 
-fn get_config(config_arg: Option<String>) -> Result<YamlLocalConfig, CliError> {
-    let config_path =
-        match config_arg {
-            Some(path) => path,
-            None => match env::var(LINKUP_CONFIG_ENV) {
-                Ok(val) => val,
-                Err(_) => return Err(CliError::NoConfig(
-                    "No config argument provided and LINKUP_CONFIG environment variable not set"
-                        .to_string(),
-                )),
-            },
-        };
+fn config_path(config_arg: Option<String>) -> Result<String, CliError> {
+    match config_arg {
+        Some(path) => Ok(path),
+        None => match env::var(LINKUP_CONFIG_ENV) {
+            Ok(val) => Ok(val),
+            Err(_) => Err(CliError::NoConfig(
+                "No config argument provided and LINKUP_CONFIG environment variable not set"
+                    .to_string(),
+            )),
+        },
+    }
+}
 
+fn get_config(config_path: String) -> Result<YamlLocalConfig, CliError> {
     let content = match fs::read_to_string(&config_path) {
         Ok(content) => content,
         Err(_) => {