diff --git a/cmd/args/appdir.go b/cmd/args/appdir.go
index dc395f1..2ac0991 100644
--- a/cmd/args/appdir.go
+++ b/cmd/args/appdir.go
@@ -2,6 +2,7 @@ package args
 
 import (
 	"errors"
+	"path/filepath"
 
 	"github.com/spf13/cobra"
 	"numerous.com/cli/cmd/output"
@@ -10,7 +11,7 @@ import (
 var ErrOptionalAppDirArgCount = errors.New("there must be at most 1 argument for optional app directory")
 
 // Returns an arguments handler, which checks an optional app dir positional
-// argument, and writes it into the given string reference.
+// argument, and writes the absolute path into the given string reference.
 func OptionalAppDir(appDir *string) func(cmd *cobra.Command, args []string) error {
 	return func(cmd *cobra.Command, args []string) error {
 		if len(args) > 1 {
@@ -21,10 +22,20 @@ func OptionalAppDir(appDir *string) func(cmd *cobra.Command, args []string) erro
 			return ErrOptionalAppDirArgCount
 		}
 
-		if len(args) == 1 {
-			*appDir = args[0]
+		// default to empty string
+		appDirArg := ""
+		if len(args) != 0 {
+			appDirArg = args[0]
 		}
 
+		// find the absolute path - current working directory if appDirArg is empty
+		absAppDir, err := filepath.Abs(appDirArg)
+		if err != nil {
+			return err
+		}
+
+		*appDir = absAppDir
+
 		return nil
 	}
 }
diff --git a/cmd/args/appdir_test.go b/cmd/args/appdir_test.go
index 23fefe6..bf91e84 100644
--- a/cmd/args/appdir_test.go
+++ b/cmd/args/appdir_test.go
@@ -1,29 +1,54 @@
 package args
 
 import (
+	"os"
+	"path/filepath"
 	"testing"
 
 	"github.com/spf13/cobra"
 	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
 )
 
 func TestOptionalAppDir(t *testing.T) {
 	t.Run("given single argument then it updates the variable", func(t *testing.T) {
-		var appDir string
+		wd := tempChdir(t)
+		type testCase struct {
+			arg      string
+			expected string
+		}
 
-		err := OptionalAppDir(&appDir)(nil, []string{"some-app-dir"})
+		for _, tc := range []testCase{
+			{
+				arg:      "relative-dir",
+				expected: filepath.Join(wd, "relative-dir"),
+			},
+			{
+				arg:      "relative/nested/dir",
+				expected: filepath.Join(wd, "relative", "nested", "dir"),
+			},
+			{
+				arg:      "/some/absolute/path",
+				expected: "/some/absolute/path",
+			},
+		} {
+			var appDir string
 
-		assert.NoError(t, err)
-		assert.Equal(t, "some-app-dir", appDir)
+			err := OptionalAppDir(&appDir)(nil, []string{tc.arg})
+
+			assert.NoError(t, err)
+			assert.Equal(t, tc.expected, appDir)
+		}
 	})
 
-	t.Run("given zero arguments then it does not update the variable", func(t *testing.T) {
+	t.Run("given zero arguments then it updates to the current directory", func(t *testing.T) {
+		wd := tempChdir(t)
 		appDir := "some-preexisting-value"
 
 		err := OptionalAppDir(&appDir)(nil, []string{})
 
 		assert.NoError(t, err)
-		assert.Equal(t, "some-preexisting-value", appDir)
+		assert.Equal(t, wd, appDir)
 	})
 
 	t.Run("given more than one argument then it returns an error", func(t *testing.T) {
@@ -34,3 +59,22 @@ func TestOptionalAppDir(t *testing.T) {
 		assert.ErrorIs(t, err, ErrOptionalAppDirArgCount)
 	})
 }
+
+// Create a temporary directory, change directory to it, return to the original
+// working directory on test cleanup. Returns the temporary directory that the
+// current directory is changed to.
+func tempChdir(t *testing.T) string {
+	t.Helper()
+
+	testWd := t.TempDir()
+	prevWd, err := os.Getwd()
+	require.NoError(t, err)
+
+	t.Cleanup(func() {
+		_ = os.Chdir(prevWd)
+	})
+
+	require.NoError(t, os.Chdir(testWd))
+
+	return testWd
+}
diff --git a/cmd/init/cmd.go b/cmd/init/cmd.go
index d4bb3b9..2680380 100644
--- a/cmd/init/cmd.go
+++ b/cmd/init/cmd.go
@@ -3,9 +3,10 @@ package init
 import (
 	"errors"
 	"fmt"
-	"os"
-	"strings"
+	"path/filepath"
 
+	"numerous.com/cli/cmd/args"
+	"numerous.com/cli/cmd/errorhandling"
 	"numerous.com/cli/cmd/group"
 	"numerous.com/cli/cmd/output"
 	"numerous.com/cli/internal/manifest"
@@ -15,12 +16,12 @@ import (
 )
 
 var Cmd = &cobra.Command{
-	Use:     "init [flags]",
+	Use:     "init [app directory]",
 	Aliases: []string{"initialize"},
 	GroupID: group.AppCommandsGroupID,
 	Short:   "Initialize a Numerous project",
 	Long:    `Helps the user bootstrap a python project as a numerous project.`,
-	Args:    cobra.MaximumNArgs(1),
+	Args:    args.OptionalAppDir(&cmdArgs.appDir),
 	RunE:    run,
 }
 
@@ -33,6 +34,7 @@ var cmdArgs struct {
 	dockerfilePath       string
 	dockerContextPath    string
 	dockerPort           uint
+	appDir               string
 }
 
 var (
@@ -41,17 +43,13 @@ var (
 )
 
 func run(cmd *cobra.Command, args []string) error {
-	appDir, err := os.Getwd()
+	absAppDir, err := filepath.Abs(cmdArgs.appDir)
 	if err != nil {
 		return ErrGetWorkDir
 	}
 
-	if len(args) != 0 {
-		appDir = PathArgumentHandler(args[0], appDir)
-	}
-
 	params := InitializeParams{
-		AppDir:           appDir,
+		AppDir:           absAppDir,
 		Name:             cmdArgs.name,
 		Desc:             cmdArgs.description,
 		LibraryKey:       cmdArgs.libraryKey,
@@ -65,7 +63,7 @@ func run(cmd *cobra.Command, args []string) error {
 	if errors.Is(err, wizard.ErrStopInit) {
 		return nil
 	} else if err != nil {
-		return err
+		return errorhandling.ErrAlreadyPrinted
 	}
 
 	printSuccess()
@@ -103,19 +101,3 @@ func init() {
 	Cmd.Flags().StringVar(&cmdArgs.dockerContextPath, "docker-context", "", "Path used as the context for building the app Dockerfile")
 	Cmd.Flags().UintVar(&cmdArgs.dockerPort, "docker-port", 0, "The port exposed in the Dockerfile")
 }
-
-func PathArgumentHandler(providedPath string, currentPath string) string {
-	appPath := providedPath
-	if providedPath != "." {
-		pathBegin := string([]rune(providedPath)[0:2])
-		if pathBegin == "./" || pathBegin == ".\\" {
-			appPath = strings.Replace(appPath, ".", currentPath, 1)
-		} else {
-			appPath = providedPath
-		}
-	} else {
-		appPath = currentPath
-	}
-
-	return appPath
-}
diff --git a/cmd/legacy/initialize/cmd.go b/cmd/legacy/initialize/cmd.go
index a7cc1db..600221a 100644
--- a/cmd/legacy/initialize/cmd.go
+++ b/cmd/legacy/initialize/cmd.go
@@ -2,8 +2,9 @@ package initialize
 
 import (
 	"fmt"
-	"os"
+	"path/filepath"
 
+	"numerous.com/cli/cmd/args"
 	cmdinit "numerous.com/cli/cmd/init"
 	"numerous.com/cli/cmd/output"
 	"numerous.com/cli/internal/dir"
@@ -20,7 +21,7 @@ var InitCmd = &cobra.Command{
 	Aliases: []string{"initialize"},
 	Short:   "Initialize a Numerous project",
 	Long:    `Helps the user bootstrap a python project as a Numerous project.`,
-	Args:    cobra.MaximumNArgs(1),
+	Args:    args.OptionalAppDir(&cmdArgs.appDir),
 	Run:     run,
 }
 
@@ -30,18 +31,15 @@ var cmdArgs struct {
 	libraryKey       string
 	appFile          string
 	requirementsFile string
+	appDir           string
 }
 
 func run(cmd *cobra.Command, args []string) {
-	appDir, err := os.Getwd()
+	appDir, err := filepath.Abs(cmdArgs.appDir)
 	if err != nil {
 		return
 	}
 
-	if len(args) != 0 {
-		appDir = cmdinit.PathArgumentHandler(args[0], appDir)
-	}
-
 	if exists, _ := dir.AppIDExists(appDir); exists {
 		printAlreadyInitialized(appDir, fmt.Sprintf("Files %q or %q exists", dir.AppIDFileName, dir.ToolIDFileName))
 		return