diff --git a/internal/sandbox/config.go b/internal/sandbox/config.go
index 1122454..3208ce2 100644
--- a/internal/sandbox/config.go
+++ b/internal/sandbox/config.go
@@ -110,6 +110,7 @@ func expandPath(pattern, cwd string) string {
 		return match
 	})
 
+	s = paths.ExpandHome(s)
 	return s
 }
 
diff --git a/pkg/env/env.go b/pkg/env/env.go
index d8a1049..02220f3 100644
--- a/pkg/env/env.go
+++ b/pkg/env/env.go
@@ -9,6 +9,8 @@ import (
 	"os"
 	"path/filepath"
 	"strings"
+
+	"ollie/pkg/paths"
 )
 
 // managed is the ordered list of env vars that ollie exposes to frontends.
@@ -82,7 +84,7 @@ func LoadFile(path string) {
 		}
 		v = strings.TrimSpace(v)
 		if k != "" && os.Getenv(k) == "" {
-			os.Setenv(k, v) //nolint:errcheck
+			os.Setenv(k, paths.ExpandHome(v)) //nolint:errcheck
 		}
 	}
 }