diff --git a/info.go b/info.go
index 323fbb8..1a4ae43 100644
--- a/info.go
+++ b/info.go
@@ -44,10 +44,12 @@ type SysInfo struct {
 	values map[string]string
 }
 
-var systemInfo = newSysInfo()
+// systemInfo is declared empty — populated in init() so Path() can be used
+// without creating an init cycle.
+var systemInfo = &SysInfo{values: make(map[string]string)}
 
-func newSysInfo() *SysInfo {
-	i := &SysInfo{values: make(map[string]string)}
+func init() {
+	i := systemInfo
 
 	// System
 	i.values["OS"] = runtime.GOOS
@@ -63,12 +65,17 @@ func newSysInfo() *SysInfo {
 		i.values["HOSTNAME"] = h
 	}
 
-	// Directories
-	if d, err := os.UserHomeDir(); err == nil {
+	// Directories — DS and DIR_HOME set first so Path() can use them.
+	// CORE_HOME overrides os.UserHomeDir() (e.g., agent workspaces).
+	if d := os.Getenv("CORE_HOME"); d != "" {
+		i.values["DIR_HOME"] = d
+	} else if d, err := os.UserHomeDir(); err == nil {
 		i.values["DIR_HOME"] = d
-		i.values["DIR_DOWNLOADS"] = d + string(os.PathSeparator) + "Downloads"
-		i.values["DIR_CODE"] = d + string(os.PathSeparator) + "Code"
 	}
+
+	// Derived directories via Path() — single point of responsibility
+	i.values["DIR_DOWNLOADS"] = Path("Downloads")
+	i.values["DIR_CODE"] = Path("Code")
 	if d, err := os.UserConfigDir(); err == nil {
 		i.values["DIR_CONFIG"] = d
 	}
@@ -83,7 +90,7 @@ func newSysInfo() *SysInfo {
 	// Platform-specific data directory
 	switch runtime.GOOS {
 	case "darwin":
-		i.values["DIR_DATA"] = i.values["DIR_HOME"] + "/Library"
+		i.values["DIR_DATA"] = Path(Env("DIR_HOME"), "Library")
 	case "windows":
 		if d := os.Getenv("LOCALAPPDATA"); d != "" {
 			i.values["DIR_DATA"] = d
@@ -91,25 +98,28 @@ func newSysInfo() *SysInfo {
 	default:
 		if xdg := os.Getenv("XDG_DATA_HOME"); xdg != "" {
 			i.values["DIR_DATA"] = xdg
-		} else if home := i.values["DIR_HOME"]; home != "" {
-			i.values["DIR_DATA"] = home + "/.local/share"
+		} else if Env("DIR_HOME") != "" {
+			i.values["DIR_DATA"] = Path(Env("DIR_HOME"), ".local", "share")
 		}
 	}
 
 	// Timestamps
 	i.values["CORE_START"] = time.Now().UTC().Format(time.RFC3339)
-
-	return i
 }
 
 // Env returns a system information value by key.
-// Returns empty string for unknown keys.
+// Core keys (OS, DIR_HOME, DS, etc.) are pre-populated at init.
+// Unknown keys fall through to os.Getenv — making Env a universal
+// replacement for os.Getenv.
 //
-//	core.Env("OS")        // "darwin"
-//	core.Env("DIR_HOME")  // "/Users/snider"
-//	core.Env("DS")        // "/"
+//	core.Env("OS")           // "darwin" (pre-populated)
+//	core.Env("DIR_HOME")     // "/Users/snider" (pre-populated)
+//	core.Env("FORGE_TOKEN")  // falls through to os.Getenv
 func Env(key string) string {
-	return systemInfo.values[key]
+	if v := systemInfo.values[key]; v != "" {
+		return v
+	}
+	return os.Getenv(key)
 }
 
 // EnvKeys returns all available environment keys.
diff --git a/path.go b/path.go
new file mode 100644
index 0000000..023419d
--- /dev/null
+++ b/path.go
@@ -0,0 +1,171 @@
+// SPDX-License-Identifier: EUPL-1.2
+
+// OS-aware filesystem path operations for the Core framework.
+// Zero filepath import — uses Env("DS") for the separator and
+// Core string primitives for all path manipulation.
+//
+// Path anchors relative segments to DIR_HOME:
+//
+//	core.Path("Code", ".core")     // "/Users/snider/Code/.core"
+//	core.Path("/tmp", "workspace") // "/tmp/workspace"
+//	core.Path()                    // "/Users/snider"
+//
+// Path component helpers:
+//
+//	core.PathBase("/Users/snider/Code/core")  // "core"
+//	core.PathDir("/Users/snider/Code/core")   // "/Users/snider/Code"
+//	core.PathExt("main.go")                   // ".go"
+package core
+
+import "path/filepath"
+
+// Path builds a clean, absolute filesystem path from segments.
+// Uses Env("DS") for the OS directory separator.
+// Relative paths are anchored to DIR_HOME. Absolute paths pass through.
+//
+//	core.Path("Code", ".core")      // "/Users/snider/Code/.core"
+//	core.Path("/tmp", "workspace")  // "/tmp/workspace"
+//	core.Path()                     // "/Users/snider"
+func Path(segments ...string) string {
+	ds := Env("DS")
+	home := Env("DIR_HOME")
+	if len(segments) == 0 {
+		return home
+	}
+	p := Join(ds, segments...)
+	if PathIsAbs(p) {
+		return CleanPath(p, ds)
+	}
+	return CleanPath(home+ds+p, ds)
+}
+
+// PathBase returns the last element of a path.
+//
+//	core.PathBase("/Users/snider/Code/core")  // "core"
+//	core.PathBase("deploy/to/homelab")        // "homelab"
+func PathBase(p string) string {
+	if p == "" {
+		return "."
+	}
+	ds := Env("DS")
+	p = TrimSuffix(p, ds)
+	if p == "" {
+		return ds
+	}
+	parts := Split(p, ds)
+	return parts[len(parts)-1]
+}
+
+// PathDir returns all but the last element of a path.
+//
+//	core.PathDir("/Users/snider/Code/core")  // "/Users/snider/Code"
+func PathDir(p string) string {
+	if p == "" {
+		return "."
+	}
+	ds := Env("DS")
+	i := lastIndex(p, ds)
+	if i < 0 {
+		return "."
+	}
+	dir := p[:i]
+	if dir == "" {
+		return ds
+	}
+	return dir
+}
+
+// PathExt returns the file extension including the dot.
+//
+//	core.PathExt("main.go")   // ".go"
+//	core.PathExt("Makefile")  // ""
+func PathExt(p string) string {
+	base := PathBase(p)
+	i := lastIndex(base, ".")
+	if i <= 0 {
+		return ""
+	}
+	return base[i:]
+}
+
+// PathIsAbs returns true if the path is absolute.
+// Handles Unix (starts with /) and Windows (drive letter like C:).
+//
+//	core.PathIsAbs("/tmp")     // true
+//	core.PathIsAbs("C:\\tmp")  // true
+//	core.PathIsAbs("relative") // false
+func PathIsAbs(p string) bool {
+	if p == "" {
+		return false
+	}
+	if p[0] == '/' {
+		return true
+	}
+	// Windows: C:\ or C:/
+	if len(p) >= 3 && p[1] == ':' && (p[2] == '/' || p[2] == '\\') {
+		return true
+	}
+	return false
+}
+
+// CleanPath removes redundant separators and resolves . and .. elements.
+//
+//	core.CleanPath("/tmp//file", "/")     // "/tmp/file"
+//	core.CleanPath("a/b/../c", "/")       // "a/c"
+func CleanPath(p, ds string) string {
+	if p == "" {
+		return "."
+	}
+
+	rooted := HasPrefix(p, ds)
+	parts := Split(p, ds)
+	var clean []string
+
+	for _, part := range parts {
+		switch part {
+		case "", ".":
+			continue
+		case "..":
+			if len(clean) > 0 && clean[len(clean)-1] != ".." {
+				clean = clean[:len(clean)-1]
+			} else if !rooted {
+				clean = append(clean, "..")
+			}
+		default:
+			clean = append(clean, part)
+		}
+	}
+
+	result := Join(ds, clean...)
+	if rooted {
+		result = ds + result
+	}
+	if result == "" {
+		if rooted {
+			return ds
+		}
+		return "."
+	}
+	return result
+}
+
+// PathGlob returns file paths matching a pattern.
+//
+//	core.PathGlob("/tmp/agent-*.log")
+func PathGlob(pattern string) []string {
+	matches, _ := filepath.Glob(pattern)
+	return matches
+}
+
+// lastIndex returns the index of the last occurrence of substr in s, or -1.
+func lastIndex(s, substr string) int {
+	if substr == "" || s == "" {
+		return -1
+	}
+	for i := len(s) - len(substr); i >= 0; i-- {
+		if s[i:i+len(substr)] == substr {
+			return i
+		}
+	}
+	return -1
+}
diff --git a/path_test.go b/path_test.go
new file mode 100644
index 0000000..56a3ac7
--- /dev/null
+++ b/path_test.go
@@ -0,0 +1,75 @@
+// SPDX-License-Identifier: EUPL-1.2
+
+package core_test
+
+import (
+	"os"
+	"testing"
+
+	core "dappco.re/go/core"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+)
+
+func TestPath_Relative(t *testing.T) {
+	home, err := os.UserHomeDir()
+	require.NoError(t, err)
+	ds := core.Env("DS")
+	assert.Equal(t, home+ds+"Code"+ds+".core", core.Path("Code", ".core"))
+}
+
+func TestPath_Absolute(t *testing.T) {
+	assert.Equal(t, "/tmp/workspace", core.Path("/tmp", "workspace"))
+}
+
+func TestPath_Empty(t *testing.T) {
+	home, err := os.UserHomeDir()
+	require.NoError(t, err)
+	assert.Equal(t, home, core.Path())
+}
+
+func TestPath_Cleans(t *testing.T) {
+	home, err := os.UserHomeDir()
+	require.NoError(t, err)
+	assert.Equal(t, home+core.Env("DS")+"Code", core.Path("Code", "sub", ".."))
+}
+
+func TestPath_CleanDoubleSlash(t *testing.T) {
+	assert.Equal(t, "/tmp/file", core.Path("/tmp//file"))
+}
+
+func TestPathBase(t *testing.T) {
+	assert.Equal(t, "core", core.PathBase("/Users/snider/Code/core"))
+	assert.Equal(t, "homelab", core.PathBase("deploy/to/homelab"))
+}
+
+func TestPathBase_Root(t *testing.T) {
+	assert.Equal(t, "/", core.PathBase("/"))
+}
+
+func TestPathBase_Empty(t *testing.T) {
+	assert.Equal(t, ".", core.PathBase(""))
+}
+
+func TestPathDir(t *testing.T) {
+	assert.Equal(t, "/Users/snider/Code", core.PathDir("/Users/snider/Code/core"))
+}
+
+func TestPathDir_Root(t *testing.T) {
+	assert.Equal(t, "/", core.PathDir("/file"))
+}
+
+func TestPathDir_NoDir(t *testing.T) {
+	assert.Equal(t, ".", core.PathDir("file.go"))
+}
+
+func TestPathExt(t *testing.T) {
+	assert.Equal(t, ".go", core.PathExt("main.go"))
+	assert.Equal(t, "", core.PathExt("Makefile"))
+	assert.Equal(t, ".gz", core.PathExt("archive.tar.gz"))
+}
+
+func TestPath_EnvConsistency(t *testing.T) {
+	// Path() and Env("DIR_HOME") should agree
+	assert.Equal(t, core.Env("DIR_HOME"), core.Path())
+}