diff --git a/internal/sandbox/config.go b/internal/sandbox/config.go
index 67d27d1..6f3c3ff 100644
--- a/internal/sandbox/config.go
+++ b/internal/sandbox/config.go
@@ -132,19 +132,20 @@ func checkPath(cfg *Config, path string, write bool, cwd string, getenv EnvFunc)
 	}
 
 	var allowed []string
-	for _, p := range cfg.Filesystem.RW {
-		allowed = append(allowed, expandPath(p, cwd, getenv))
-	}
-	for _, p := range cfg.Filesystem.RWX {
-		allowed = append(allowed, expandPath(p, cwd, getenv))
+	expandAndSplit := func(entries []string) {
+		for _, p := range entries {
+			for _, ep := range strings.Split(expandPath(p, cwd, getenv), ":") {
+				if ep != "" {
+					allowed = append(allowed, ep)
+				}
+			}
+		}
 	}
+	expandAndSplit(cfg.Filesystem.RW)
+	expandAndSplit(cfg.Filesystem.RWX)
 	if !write {
-		for _, p := range cfg.Filesystem.RO {
-			allowed = append(allowed, expandPath(p, cwd, getenv))
-		}
-		for _, p := range cfg.Filesystem.ROX {
-			allowed = append(allowed, expandPath(p, cwd, getenv))
-		}
+		expandAndSplit(cfg.Filesystem.RO)
+		expandAndSplit(cfg.Filesystem.ROX)
 	}
 
 	for _, root := range allowed {
diff --git a/internal/sandbox/sandbox_test.go b/internal/sandbox/sandbox_test.go
index ba5e7d7..627c93f 100644
--- a/internal/sandbox/sandbox_test.go
+++ b/internal/sandbox/sandbox_test.go
@@ -675,6 +675,71 @@ func TestIsSuperpowerdRunning_XDGFallback(t *testing.T) {
 	}
 }
 
+func TestWrapCommand_ColonSeparatedPaths(t *testing.T) {
+	tmpDir := t.TempDir()
+	dir1 := filepath.Join(tmpDir, "skills1")
+	dir2 := filepath.Join(tmpDir, "skills2")
+	os.MkdirAll(dir1, 0755)
+	os.MkdirAll(dir2, 0755)
+
+	// Simulate OLLIE_SKILLS_PATH="/path1:/path2"
+	t.Setenv("OLLIE_SKILLS_PATH", dir1+":"+dir2)
+
+	cfg := &Config{
+		Filesystem: FilesystemConfig{
+			RWX: []string{"{OLLIE_SKILLS_PATH}"},
+		},
+	}
+	got := mustWrapCommand(t, cfg, []string{"sh"}, tmpDir)
+	assertFlagValue(t, got, "--rwx", dir1)
+	assertFlagValue(t, got, "--rwx", dir2)
+}
+
+func TestCheckPath_ColonSeparatedPaths(t *testing.T) {
+	tmpDir := t.TempDir()
+	dir1 := filepath.Join(tmpDir, "skills1")
+	dir2 := filepath.Join(tmpDir, "skills2")
+	os.MkdirAll(dir1, 0755)
+	os.MkdirAll(dir2, 0755)
+
+	file1 := filepath.Join(dir1, "test.md")
+	os.WriteFile(file1, []byte("hi"), 0644)
+	file2 := filepath.Join(dir2, "test.md")
+	os.WriteFile(file2, []byte("hi"), 0644)
+
+	getenv := func(k string) string {
+		if k == "OLLIE_SKILLS_PATH" {
+			return dir1 + ":" + dir2
+		}
+		if k == "HOME" {
+			return tmpDir
+		}
+		return ""
+	}
+
+	cfg := &Config{
+		Filesystem: FilesystemConfig{
+			RWX: []string{"{OLLIE_SKILLS_PATH}"},
+		},
+	}
+
+	// Both paths should be allowed for read
+	if err := checkPath(cfg, file1, false, tmpDir, getenv); err != nil {
+		t.Errorf("file in dir1 should be allowed: %v", err)
+	}
+	if err := checkPath(cfg, file2, false, tmpDir, getenv); err != nil {
+		t.Errorf("file in dir2 should be allowed: %v", err)
+	}
+
+	// Path outside both should be denied
+	outside := filepath.Join(tmpDir, "outside", "file.txt")
+	os.MkdirAll(filepath.Dir(outside), 0755)
+	os.WriteFile(outside, []byte("x"), 0644)
+	if err := checkPath(cfg, outside, false, tmpDir, getenv); err == nil {
+		t.Error("path outside both dirs should be denied")
+	}
+}
+
 func TestIsSuperpowerdRunning_SocketExists(t *testing.T) {
 	tmpDir := t.TempDir()
 	sockPath := filepath.Join(tmpDir, "superpowerd.sock")
diff --git a/internal/sandbox/wrapper.go b/internal/sandbox/wrapper.go
index 2e37679..27ec488 100644
--- a/internal/sandbox/wrapper.go
+++ b/internal/sandbox/wrapper.go
@@ -7,6 +7,7 @@ import (
 	"os/exec"
 	"path/filepath"
 	"sort"
+	"strings"
 )
 
 // pathEntry holds a path with its permission type
@@ -49,30 +50,21 @@ func WrapCommand(cfg *Config, originalCmd []string, cwd string, getenv EnvFunc)
 	}
 
 	var entries []pathEntry
-	for _, path := range cfg.Filesystem.RO {
-		expanded := expandPath(path, cwd, getenv)
-		if pathExists(expanded) {
-			entries = append(entries, pathEntry{expanded, "--ro"})
-		}
-	}
-	for _, path := range cfg.Filesystem.ROX {
-		expanded := expandPath(path, cwd, getenv)
-		if pathExists(expanded) {
-			entries = append(entries, pathEntry{expanded, "--rox"})
-		}
-	}
-	for _, path := range cfg.Filesystem.RW {
-		expanded := expandPath(path, cwd, getenv)
-		if pathExists(expanded) {
-			entries = append(entries, pathEntry{expanded, "--rw"})
-		}
-	}
-	for _, path := range cfg.Filesystem.RWX {
-		expanded := expandPath(path, cwd, getenv)
-		if pathExists(expanded) {
-			entries = append(entries, pathEntry{expanded, "--rwx"})
+	addPaths := func(paths []string, flag string) {
+		for _, path := range paths {
+			expanded := expandPath(path, cwd, getenv)
+			// Handle colon-separated paths (e.g. OLLIE_SKILLS_PATH)
+			for _, p := range strings.Split(expanded, ":") {
+				if p != "" && pathExists(p) {
+					entries = append(entries, pathEntry{p, flag})
+				}
+			}
 		}
 	}
+	addPaths(cfg.Filesystem.RO, "--ro")
+	addPaths(cfg.Filesystem.ROX, "--rox")
+	addPaths(cfg.Filesystem.RW, "--rw")
+	addPaths(cfg.Filesystem.RWX, "--rwx")
 
 	// Sort so parents come before children
 	sort.Slice(entries, func(i, j int) bool {