diff --git a/cmd/add.go b/cmd/add.go
index 675ba8a..1f777b2 100644
--- a/cmd/add.go
+++ b/cmd/add.go
@@ -1,7 +1,6 @@
 package cmd
 
 import (
-	"fmt"
 	"path/filepath"
 
 	"github.com/spf13/cobra"
@@ -10,11 +9,12 @@ import (
 
 func newAddCmd() *cobra.Command {
 	cmd := &cobra.Command{
-		Use:          "add <file>",
-		Short:        "✨ Add a file to lnk management",
-		Long:         "Moves a file to the lnk repository and creates a symlink in its place.",
-		Args:         cobra.ExactArgs(1),
-		SilenceUsage: true,
+		Use:           "add <file>",
+		Short:         "✨ Add a file to lnk management",
+		Long:          "Moves a file to the lnk repository and creates a symlink in its place.",
+		Args:          cobra.ExactArgs(1),
+		SilenceUsage:  true,
+		SilenceErrors: true,
 		RunE: func(cmd *cobra.Command, args []string) error {
 			filePath := args[0]
 			host, _ := cmd.Flags().GetString("host")
@@ -22,7 +22,7 @@ func newAddCmd() *cobra.Command {
 			lnk := core.NewLnk(core.WithHost(host))
 
 			if err := lnk.Add(filePath); err != nil {
-				return fmt.Errorf("failed to add file: %w", err)
+				return err
 			}
 
 			basename := filepath.Base(filePath)
diff --git a/cmd/init.go b/cmd/init.go
index 08d9d6f..9ac4fcd 100644
--- a/cmd/init.go
+++ b/cmd/init.go
@@ -1,24 +1,23 @@
 package cmd
 
 import (
-	"fmt"
-
 	"github.com/spf13/cobra"
 	"github.com/yarlson/lnk/internal/core"
 )
 
 func newInitCmd() *cobra.Command {
 	cmd := &cobra.Command{
-		Use:          "init",
-		Short:        "🎯 Initialize a new lnk repository",
-		Long:         "Creates the lnk directory and initializes a Git repository for managing dotfiles.",
-		SilenceUsage: true,
+		Use:           "init",
+		Short:         "🎯 Initialize a new lnk repository",
+		Long:          "Creates the lnk directory and initializes a Git repository for managing dotfiles.",
+		SilenceUsage:  true,
+		SilenceErrors: true,
 		RunE: func(cmd *cobra.Command, args []string) error {
 			remote, _ := cmd.Flags().GetString("remote")
 
 			lnk := core.NewLnk()
 			if err := lnk.InitWithRemote(remote); err != nil {
-				return fmt.Errorf("failed to initialize lnk: %w", err)
+				return err
 			}
 
 			if remote != "" {
diff --git a/cmd/list.go b/cmd/list.go
index 890c091..811537d 100644
--- a/cmd/list.go
+++ b/cmd/list.go
@@ -1,7 +1,6 @@
 package cmd
 
 import (
-	"fmt"
 	"os"
 	"path/filepath"
 	"strings"
@@ -12,10 +11,11 @@ import (
 
 func newListCmd() *cobra.Command {
 	cmd := &cobra.Command{
-		Use:          "list",
-		Short:        "📋 List files managed by lnk",
-		Long:         "Display all files and directories currently managed by lnk.",
-		SilenceUsage: true,
+		Use:           "list",
+		Short:         "📋 List files managed by lnk",
+		Long:          "Display all files and directories currently managed by lnk.",
+		SilenceUsage:  true,
+		SilenceErrors: true,
 		RunE: func(cmd *cobra.Command, args []string) error {
 			host, _ := cmd.Flags().GetString("host")
 			all, _ := cmd.Flags().GetBool("all")
@@ -44,7 +44,7 @@ func listCommonConfig(cmd *cobra.Command) error {
 	lnk := core.NewLnk()
 	managedItems, err := lnk.List()
 	if err != nil {
-		return fmt.Errorf("failed to list managed items: %w", err)
+		return err
 	}
 
 	if len(managedItems) == 0 {
@@ -71,7 +71,7 @@ func listHostConfig(cmd *cobra.Command, host string) error {
 	lnk := core.NewLnk(core.WithHost(host))
 	managedItems, err := lnk.List()
 	if err != nil {
-		return fmt.Errorf("failed to list managed items for host %s: %w", host, err)
+		return err
 	}
 
 	if len(managedItems) == 0 {
@@ -101,7 +101,7 @@ func listAllConfigs(cmd *cobra.Command) error {
 	lnk := core.NewLnk()
 	commonItems, err := lnk.List()
 	if err != nil {
-		return fmt.Errorf("failed to list common managed items: %w", err)
+		return err
 	}
 
 	printf(cmd, "🌐 \033[1mCommon configuration\033[0m (\033[36m%d item", len(commonItems))
@@ -121,7 +121,7 @@ func listAllConfigs(cmd *cobra.Command) error {
 	// Find all host-specific configurations
 	hosts, err := findHostConfigs()
 	if err != nil {
-		return fmt.Errorf("failed to find host configurations: %w", err)
+		return err
 	}
 
 	for _, host := range hosts {
@@ -163,7 +163,7 @@ func findHostConfigs() ([]string, error) {
 
 	entries, err := os.ReadDir(repoPath)
 	if err != nil {
-		return nil, fmt.Errorf("failed to read repository directory: %w", err)
+		return nil, err
 	}
 
 	var hosts []string
diff --git a/cmd/pull.go b/cmd/pull.go
index c3a8bdc..ccf722e 100644
--- a/cmd/pull.go
+++ b/cmd/pull.go
@@ -1,18 +1,17 @@
 package cmd
 
 import (
-	"fmt"
-
 	"github.com/spf13/cobra"
 	"github.com/yarlson/lnk/internal/core"
 )
 
 func newPullCmd() *cobra.Command {
 	cmd := &cobra.Command{
-		Use:          "pull",
-		Short:        "⬇️ Pull changes from remote and restore symlinks",
-		Long:         "Fetches changes from remote repository and automatically restores symlinks for all managed files.",
-		SilenceUsage: true,
+		Use:           "pull",
+		Short:         "⬇️ Pull changes from remote and restore symlinks",
+		Long:          "Fetches changes from remote repository and automatically restores symlinks for all managed files.",
+		SilenceUsage:  true,
+		SilenceErrors: true,
 		RunE: func(cmd *cobra.Command, args []string) error {
 			host, _ := cmd.Flags().GetString("host")
 
@@ -20,7 +19,7 @@ func newPullCmd() *cobra.Command {
 
 			restored, err := lnk.Pull()
 			if err != nil {
-				return fmt.Errorf("failed to pull changes: %w", err)
+				return err
 			}
 
 			if len(restored) > 0 {
diff --git a/cmd/push.go b/cmd/push.go
index eb992be..47cbb09 100644
--- a/cmd/push.go
+++ b/cmd/push.go
@@ -1,19 +1,18 @@
 package cmd
 
 import (
-	"fmt"
-
 	"github.com/spf13/cobra"
 	"github.com/yarlson/lnk/internal/core"
 )
 
 func newPushCmd() *cobra.Command {
 	return &cobra.Command{
-		Use:          "push [message]",
-		Short:        "🚀 Push local changes to remote repository",
-		Long:         "Stages all changes, creates a sync commit with the provided message, and pushes to remote.",
-		Args:         cobra.MaximumNArgs(1),
-		SilenceUsage: true,
+		Use:           "push [message]",
+		Short:         "🚀 Push local changes to remote repository",
+		Long:          "Stages all changes, creates a sync commit with the provided message, and pushes to remote.",
+		Args:          cobra.MaximumNArgs(1),
+		SilenceUsage:  true,
+		SilenceErrors: true,
 		RunE: func(cmd *cobra.Command, args []string) error {
 			message := "lnk: sync configuration files"
 			if len(args) > 0 {
@@ -22,7 +21,7 @@ func newPushCmd() *cobra.Command {
 
 			lnk := core.NewLnk()
 			if err := lnk.Push(message); err != nil {
-				return fmt.Errorf("failed to push changes: %w", err)
+				return err
 			}
 
 			printf(cmd, "🚀 \033[1;32mSuccessfully pushed changes\033[0m\n")
diff --git a/cmd/rm.go b/cmd/rm.go
index 9c030c5..26acf3f 100644
--- a/cmd/rm.go
+++ b/cmd/rm.go
@@ -1,7 +1,6 @@
 package cmd
 
 import (
-	"fmt"
 	"path/filepath"
 
 	"github.com/spf13/cobra"
@@ -10,11 +9,12 @@ import (
 
 func newRemoveCmd() *cobra.Command {
 	cmd := &cobra.Command{
-		Use:          "rm <file>",
-		Short:        "🗑️ Remove a file from lnk management",
-		Long:         "Removes a symlink and restores the original file from the lnk repository.",
-		Args:         cobra.ExactArgs(1),
-		SilenceUsage: true,
+		Use:           "rm <file>",
+		Short:         "🗑️ Remove a file from lnk management",
+		Long:          "Removes a symlink and restores the original file from the lnk repository.",
+		Args:          cobra.ExactArgs(1),
+		SilenceUsage:  true,
+		SilenceErrors: true,
 		RunE: func(cmd *cobra.Command, args []string) error {
 			filePath := args[0]
 			host, _ := cmd.Flags().GetString("host")
@@ -22,7 +22,7 @@ func newRemoveCmd() *cobra.Command {
 			lnk := core.NewLnk(core.WithHost(host))
 
 			if err := lnk.Remove(filePath); err != nil {
-				return fmt.Errorf("failed to remove file: %w", err)
+				return err
 			}
 
 			basename := filepath.Base(filePath)
diff --git a/cmd/root.go b/cmd/root.go
index cae5935..d042c73 100644
--- a/cmd/root.go
+++ b/cmd/root.go
@@ -32,8 +32,9 @@ Supports both common configurations and host-specific setups.
   lnk push "setup complete"        # Sync to remote
 
 🎯 Simple, fast, Git-native, and multi-host ready.`,
-		SilenceUsage: true,
-		Version:      fmt.Sprintf("%s (built %s)", version, buildTime),
+		SilenceUsage:  true,
+		SilenceErrors: true,
+		Version:       fmt.Sprintf("%s (built %s)", version, buildTime),
 	}
 
 	// Add subcommands
@@ -57,7 +58,7 @@ func SetVersion(v, bt string) {
 func Execute() {
 	rootCmd := NewRootCommand()
 	if err := rootCmd.Execute(); err != nil {
-		fmt.Fprintln(os.Stderr, err)
+		_, _ = fmt.Fprintln(os.Stderr, err)
 		os.Exit(1)
 	}
 }
diff --git a/cmd/root_test.go b/cmd/root_test.go
index 1102331..944de63 100644
--- a/cmd/root_test.go
+++ b/cmd/root_test.go
@@ -157,7 +157,7 @@ func (suite *CLITestSuite) TestStatusCommand() {
 	// Test status without remote - should fail
 	err = suite.runCommand("status")
 	suite.Error(err)
-	suite.Contains(err.Error(), "no remote configured")
+	suite.Contains(err.Error(), "No remote repository is configured")
 }
 
 func (suite *CLITestSuite) TestListCommand() {
@@ -247,7 +247,7 @@ func (suite *CLITestSuite) TestErrorHandling() {
 			name:        "add nonexistent file",
 			args:        []string{"add", "/nonexistent/file"},
 			wantErr:     true,
-			errContains: "File does not exist",
+			errContains: "File or directory not found",
 		},
 		{
 			name:        "status without init",
diff --git a/cmd/status.go b/cmd/status.go
index 8544d7a..46415d3 100644
--- a/cmd/status.go
+++ b/cmd/status.go
@@ -1,23 +1,22 @@
 package cmd
 
 import (
-	"fmt"
-
 	"github.com/spf13/cobra"
 	"github.com/yarlson/lnk/internal/core"
 )
 
 func newStatusCmd() *cobra.Command {
 	return &cobra.Command{
-		Use:          "status",
-		Short:        "📊 Show repository sync status",
-		Long:         "Display how many commits ahead/behind the local repository is relative to the remote and check for uncommitted changes.",
-		SilenceUsage: true,
+		Use:           "status",
+		Short:         "📊 Show repository sync status",
+		Long:          "Display how many commits ahead/behind the local repository is relative to the remote and check for uncommitted changes.",
+		SilenceUsage:  true,
+		SilenceErrors: true,
 		RunE: func(cmd *cobra.Command, args []string) error {
 			lnk := core.NewLnk()
 			status, err := lnk.Status()
 			if err != nil {
-				return fmt.Errorf("failed to get status: %w", err)
+				return err
 			}
 
 			if status.Dirty {
diff --git a/internal/core/lnk.go b/internal/core/lnk.go
index 75cdddf..a082fa6 100644
--- a/internal/core/lnk.go
+++ b/internal/core/lnk.go
@@ -141,27 +141,17 @@ func (l *Lnk) InitWithRemote(remoteURL string) error {
 	}
 
 	// No existing repository, initialize Git repository
-	if err := l.git.Init(); err != nil {
-		return fmt.Errorf("failed to initialize git repository: %w", err)
-	}
-
-	return nil
+	return l.git.Init()
 }
 
 // Clone clones a repository from the given URL
 func (l *Lnk) Clone(url string) error {
-	if err := l.git.Clone(url); err != nil {
-		return fmt.Errorf("failed to clone repository: %w", err)
-	}
-	return nil
+	return l.git.Clone(url)
 }
 
 // AddRemote adds a remote to the repository
 func (l *Lnk) AddRemote(name, url string) error {
-	if err := l.git.AddRemote(name, url); err != nil {
-		return fmt.Errorf("failed to add remote %s: %w", name, err)
-	}
-	return nil
+	return l.git.AddRemote(name, url)
 }
 
 // Add moves a file or directory to the repository and creates a symlink
@@ -211,36 +201,22 @@ func (l *Lnk) Add(filePath string) error {
 	}
 
 	// Move to repository (handles both files and directories)
-	if info.IsDir() {
-		if err := l.fs.MoveDirectory(absPath, destPath); err != nil {
-			return fmt.Errorf("failed to move directory to repository: %w", err)
-		}
-	} else {
-		if err := l.fs.MoveFile(absPath, destPath); err != nil {
-			return fmt.Errorf("failed to move file to repository: %w", err)
-		}
+	if err := l.fs.Move(absPath, destPath, info); err != nil {
+		return err
 	}
 
 	// Create symlink
 	if err := l.fs.CreateSymlink(destPath, absPath); err != nil {
 		// Try to restore the original if symlink creation fails
-		if info.IsDir() {
-			_ = l.fs.MoveDirectory(destPath, absPath) // Ignore error in cleanup
-		} else {
-			_ = l.fs.MoveFile(destPath, absPath) // Ignore error in cleanup
-		}
-		return fmt.Errorf("failed to create symlink: %w", err)
+		_ = l.fs.Move(destPath, absPath, info)
+		return err
 	}
 
 	// Add to .lnk tracking file using relative path
 	if err := l.addManagedItem(relativePath); err != nil {
 		// Try to restore the original state if tracking fails
-		_ = os.Remove(absPath) // Ignore error in cleanup
-		if info.IsDir() {
-			_ = l.fs.MoveDirectory(destPath, absPath) // Ignore error in cleanup
-		} else {
-			_ = l.fs.MoveFile(destPath, absPath) // Ignore error in cleanup
-		}
+		_ = os.Remove(absPath)
+		_ = l.fs.Move(destPath, absPath, info)
 		return fmt.Errorf("failed to update tracking file: %w", err)
 	}
 
@@ -252,41 +228,29 @@ func (l *Lnk) Add(filePath string) error {
 	}
 	if err := l.git.Add(gitPath); err != nil {
 		// Try to restore the original state if git add fails
-		_ = os.Remove(absPath)                // Ignore error in cleanup
-		_ = l.removeManagedItem(relativePath) // Ignore error in cleanup
-		if info.IsDir() {
-			_ = l.fs.MoveDirectory(destPath, absPath) // Ignore error in cleanup
-		} else {
-			_ = l.fs.MoveFile(destPath, absPath) // Ignore error in cleanup
-		}
-		return fmt.Errorf("failed to add item to git: %w", err)
+		_ = os.Remove(absPath)
+		_ = l.removeManagedItem(relativePath)
+		_ = l.fs.Move(destPath, absPath, info)
+		return err
 	}
 
 	// Add .lnk file to the same commit
 	if err := l.git.Add(l.getLnkFileName()); err != nil {
 		// Try to restore the original state if git add fails
-		_ = os.Remove(absPath)                // Ignore error in cleanup
-		_ = l.removeManagedItem(relativePath) // Ignore error in cleanup
-		if info.IsDir() {
-			_ = l.fs.MoveDirectory(destPath, absPath) // Ignore error in cleanup
-		} else {
-			_ = l.fs.MoveFile(destPath, absPath) // Ignore error in cleanup
-		}
-		return fmt.Errorf("failed to add .lnk file to git: %w", err)
+		_ = os.Remove(absPath)
+		_ = l.removeManagedItem(relativePath)
+		_ = l.fs.Move(destPath, absPath, info)
+		return err
 	}
 
 	// Commit both changes together
 	basename := filepath.Base(relativePath)
 	if err := l.git.Commit(fmt.Sprintf("lnk: added %s", basename)); err != nil {
 		// Try to restore the original state if commit fails
-		_ = os.Remove(absPath)                // Ignore error in cleanup
-		_ = l.removeManagedItem(relativePath) // Ignore error in cleanup
-		if info.IsDir() {
-			_ = l.fs.MoveDirectory(destPath, absPath) // Ignore error in cleanup
-		} else {
-			_ = l.fs.MoveFile(destPath, absPath) // Ignore error in cleanup
-		}
-		return fmt.Errorf("failed to commit changes: %w", err)
+		_ = os.Remove(absPath)
+		_ = l.removeManagedItem(relativePath)
+		_ = l.fs.Move(destPath, absPath, info)
+		return err
 	}
 
 	return nil
@@ -361,29 +325,23 @@ func (l *Lnk) Remove(filePath string) error {
 		gitPath = filepath.Join(l.host+".lnk", relativePath)
 	}
 	if err := l.git.Remove(gitPath); err != nil {
-		return fmt.Errorf("failed to remove from git: %w", err)
+		return err
 	}
 
 	// Add .lnk file to the same commit
 	if err := l.git.Add(l.getLnkFileName()); err != nil {
-		return fmt.Errorf("failed to add .lnk file to git: %w", err)
+		return err
 	}
 
 	// Commit both changes together
 	basename := filepath.Base(relativePath)
 	if err := l.git.Commit(fmt.Sprintf("lnk: removed %s", basename)); err != nil {
-		return fmt.Errorf("failed to commit changes: %w", err)
+		return err
 	}
 
 	// Move back from repository (handles both files and directories)
-	if info.IsDir() {
-		if err := l.fs.MoveDirectory(target, absPath); err != nil {
-			return fmt.Errorf("failed to restore directory: %w", err)
-		}
-	} else {
-		if err := l.fs.MoveFile(target, absPath); err != nil {
-			return fmt.Errorf("failed to restore file: %w", err)
-		}
+	if err := l.fs.Move(target, absPath, info); err != nil {
+		return err
 	}
 
 	return nil
@@ -411,7 +369,7 @@ func (l *Lnk) Status() (*StatusInfo, error) {
 
 	gitStatus, err := l.git.GetStatus()
 	if err != nil {
-		return nil, fmt.Errorf("failed to get repository status: %w", err)
+		return nil, err
 	}
 
 	return &StatusInfo{
@@ -432,28 +390,24 @@ func (l *Lnk) Push(message string) error {
 	// Check if there are any changes
 	hasChanges, err := l.git.HasChanges()
 	if err != nil {
-		return fmt.Errorf("failed to check for changes: %w", err)
+		return err
 	}
 
 	if hasChanges {
 		// Stage all changes
 		if err := l.git.AddAll(); err != nil {
-			return fmt.Errorf("failed to stage changes: %w", err)
+			return err
 		}
 
 		// Create a sync commit
 		if err := l.git.Commit(message); err != nil {
-			return fmt.Errorf("failed to commit changes: %w", err)
+			return err
 		}
 	}
 
 	// Push to remote (this will be a no-op in tests since we don't have real remotes)
 	// In real usage, this would push to the actual remote repository
-	if err := l.git.Push(); err != nil {
-		return fmt.Errorf("failed to push to remote: %w", err)
-	}
-
-	return nil
+	return l.git.Push()
 }
 
 // Pull fetches changes from remote and restores symlinks as needed
@@ -465,7 +419,7 @@ func (l *Lnk) Pull() ([]string, error) {
 
 	// Pull changes from remote (this will be a no-op in tests since we don't have real remotes)
 	if err := l.git.Pull(); err != nil {
-		return nil, fmt.Errorf("failed to pull from remote: %w", err)
+		return nil, err
 	}
 
 	// Find all managed files in the repository and restore symlinks
@@ -541,7 +495,7 @@ func (l *Lnk) RestoreSymlinks() ([]string, error) {
 
 		// Create symlink
 		if err := l.fs.CreateSymlink(repoItem, symlinkPath); err != nil {
-			return nil, fmt.Errorf("failed to create symlink for %s: %w", relativePath, err)
+			return nil, err
 		}
 
 		restored = append(restored, relativePath)
diff --git a/internal/core/lnk_test.go b/internal/core/lnk_test.go
index 9798982..0043fae 100644
--- a/internal/core/lnk_test.go
+++ b/internal/core/lnk_test.go
@@ -275,7 +275,7 @@ func (suite *CoreTestSuite) TestErrorConditions() {
 
 	err = suite.lnk.Add("/nonexistent/file")
 	suite.Error(err)
-	suite.Contains(err.Error(), "File does not exist")
+	suite.Contains(err.Error(), "File or directory not found")
 
 	// Test remove unmanaged file
 	testFile := filepath.Join(suite.tempDir, ".regularfile")
@@ -289,7 +289,7 @@ func (suite *CoreTestSuite) TestErrorConditions() {
 	// Test status without remote
 	_, err = suite.lnk.Status()
 	suite.Error(err)
-	suite.Contains(err.Error(), "no remote configured")
+	suite.Contains(err.Error(), "No remote repository is configured")
 }
 
 // Test git operations
diff --git a/internal/fs/errors.go b/internal/fs/errors.go
new file mode 100644
index 0000000..850a388
--- /dev/null
+++ b/internal/fs/errors.go
@@ -0,0 +1,119 @@
+package fs
+
+import "fmt"
+
+// ANSI color codes for consistent formatting
+const (
+	colorReset = "\033[0m"
+	colorRed   = "\033[31m"
+	colorBold  = "\033[1m"
+)
+
+// formatError creates a consistently formatted error message with ❌ prefix
+func formatError(message string, args ...interface{}) string {
+	return fmt.Sprintf("❌ "+message, args...)
+}
+
+// formatPath formats a file path with red color
+func formatPath(path string) string {
+	return fmt.Sprintf("%s%s%s", colorRed, path, colorReset)
+}
+
+// formatCommand formats a command with bold styling
+func formatCommand(command string) string {
+	return fmt.Sprintf("%s%s%s", colorBold, command, colorReset)
+}
+
+// FileNotExistsError represents an error when a file does not exist
+type FileNotExistsError struct {
+	Path string
+	Err  error
+}
+
+func (e *FileNotExistsError) Error() string {
+	return formatError("File or directory not found: %s", formatPath(e.Path))
+}
+
+func (e *FileNotExistsError) Unwrap() error {
+	return e.Err
+}
+
+// FileCheckError represents an error when failing to check a file
+type FileCheckError struct {
+	Err error
+}
+
+func (e *FileCheckError) Error() string {
+	return formatError("Unable to access file. Please check file permissions and try again.")
+}
+
+func (e *FileCheckError) Unwrap() error {
+	return e.Err
+}
+
+// UnsupportedFileTypeError represents an error when a file type is not supported
+type UnsupportedFileTypeError struct {
+	Path string
+}
+
+func (e *UnsupportedFileTypeError) Error() string {
+	return formatError("Cannot manage this type of file: %s\n   💡 lnk can only manage regular files and directories", formatPath(e.Path))
+}
+
+func (e *UnsupportedFileTypeError) Unwrap() error {
+	return nil
+}
+
+// NotManagedByLnkError represents an error when a file is not managed by lnk
+type NotManagedByLnkError struct {
+	Path string
+}
+
+func (e *NotManagedByLnkError) Error() string {
+	return formatError("File is not managed by lnk: %s\n   💡 Use %s to manage this file first",
+		formatPath(e.Path), formatCommand("lnk add"))
+}
+
+func (e *NotManagedByLnkError) Unwrap() error {
+	return nil
+}
+
+// SymlinkReadError represents an error when failing to read a symlink
+type SymlinkReadError struct {
+	Err error
+}
+
+func (e *SymlinkReadError) Error() string {
+	return formatError("Unable to read symlink. The file may be corrupted or have invalid permissions.")
+}
+
+func (e *SymlinkReadError) Unwrap() error {
+	return e.Err
+}
+
+// DirectoryCreationError represents an error when failing to create a directory
+type DirectoryCreationError struct {
+	Operation string
+	Err       error
+}
+
+func (e *DirectoryCreationError) Error() string {
+	return formatError("Failed to create directory. Please check permissions and available disk space.")
+}
+
+func (e *DirectoryCreationError) Unwrap() error {
+	return e.Err
+}
+
+// RelativePathCalculationError represents an error when failing to calculate relative path
+type RelativePathCalculationError struct {
+	Err error
+}
+
+func (e *RelativePathCalculationError) Error() string {
+	return formatError("Unable to create symlink due to path configuration issues. Please check file locations.")
+}
+
+func (e *RelativePathCalculationError) Unwrap() error {
+	return e.Err
+}
diff --git a/internal/fs/filesystem.go b/internal/fs/filesystem.go
index 996e492..de37dd7 100644
--- a/internal/fs/filesystem.go
+++ b/internal/fs/filesystem.go
@@ -1,7 +1,6 @@
 package fs
 
 import (
-	"fmt"
 	"os"
 	"path/filepath"
 	"strings"
@@ -17,18 +16,19 @@ func New() *FileSystem {
 
 // ValidateFileForAdd validates that a file or directory can be added to lnk
 func (fs *FileSystem) ValidateFileForAdd(filePath string) error {
-	// Check if file exists
+	// Check if file exists and get its info
 	info, err := os.Stat(filePath)
 	if err != nil {
 		if os.IsNotExist(err) {
-			return fmt.Errorf("❌ File does not exist: \033[31m%s\033[0m", filePath)
+			return &FileNotExistsError{Path: filePath, Err: err}
 		}
-		return fmt.Errorf("❌ Failed to check file: %w", err)
+
+		return &FileCheckError{Err: err}
 	}
 
 	// Allow both regular files and directories
 	if !info.Mode().IsRegular() && !info.IsDir() {
-		return fmt.Errorf("❌ Only regular files and directories are supported: \033[31m%s\033[0m", filePath)
+		return &UnsupportedFileTypeError{Path: filePath}
 	}
 
 	return nil
@@ -36,98 +36,79 @@ func (fs *FileSystem) ValidateFileForAdd(filePath string) error {
 
 // ValidateSymlinkForRemove validates that a symlink can be removed from lnk
 func (fs *FileSystem) ValidateSymlinkForRemove(filePath, repoPath string) error {
-	// Check if file exists
+	// Check if file exists and is a symlink
 	info, err := os.Lstat(filePath) // Use Lstat to not follow symlinks
 	if err != nil {
 		if os.IsNotExist(err) {
-			return fmt.Errorf("❌ File does not exist: \033[31m%s\033[0m", filePath)
+			return &FileNotExistsError{Path: filePath, Err: err}
 		}
-		return fmt.Errorf("❌ Failed to check file: %w", err)
+
+		return &FileCheckError{Err: err}
 	}
 
-	// Check if it's a symlink
 	if info.Mode()&os.ModeSymlink == 0 {
-		return fmt.Errorf("❌ File is not managed by lnk: \033[31m%s\033[0m\n   💡 Use \033[1mlnk add\033[0m to manage this file first", filePath)
+		return &NotManagedByLnkError{Path: filePath}
 	}
 
-	// Check if symlink points to the repository
+	// Get symlink target and resolve to absolute path
 	target, err := os.Readlink(filePath)
 	if err != nil {
-		return fmt.Errorf("failed to read symlink: %w", err)
+		return &SymlinkReadError{Err: err}
 	}
 
-	// Convert relative path to absolute if needed
 	if !filepath.IsAbs(target) {
 		target = filepath.Join(filepath.Dir(filePath), target)
 	}
 
-	// Clean the path to resolve any .. or . components
+	// Clean paths and check if target is inside the repository
 	target = filepath.Clean(target)
 	repoPath = filepath.Clean(repoPath)
 
-	// Check if target is inside the repository
 	if !strings.HasPrefix(target, repoPath+string(filepath.Separator)) && target != repoPath {
-		return fmt.Errorf("❌ File is not managed by lnk: \033[31m%s\033[0m", filePath)
+		return &NotManagedByLnkError{Path: filePath}
 	}
 
 	return nil
 }
 
+// Move moves a file or directory from source to destination based on the file info
+func (fs *FileSystem) Move(src, dst string, info os.FileInfo) error {
+	if info.IsDir() {
+		return fs.MoveDirectory(src, dst)
+	}
+	return fs.MoveFile(src, dst)
+}
+
 // MoveFile moves a file from source to destination
 func (fs *FileSystem) MoveFile(src, dst string) error {
 	// Ensure destination directory exists
-	dstDir := filepath.Dir(dst)
-	if err := os.MkdirAll(dstDir, 0755); err != nil {
-		return fmt.Errorf("failed to create destination directory: %w", err)
+	if err := os.MkdirAll(filepath.Dir(dst), 0755); err != nil {
+		return &DirectoryCreationError{Operation: "destination directory", Err: err}
 	}
 
 	// Move the file
-	if err := os.Rename(src, dst); err != nil {
-		return fmt.Errorf("failed to move file from %s to %s: %w", src, dst, err)
-	}
-
-	return nil
+	return os.Rename(src, dst)
 }
 
 // CreateSymlink creates a relative symlink from target to linkPath
 func (fs *FileSystem) CreateSymlink(target, linkPath string) error {
 	// Calculate relative path from linkPath to target
-	linkDir := filepath.Dir(linkPath)
-	relTarget, err := filepath.Rel(linkDir, target)
+	relTarget, err := filepath.Rel(filepath.Dir(linkPath), target)
 	if err != nil {
-		return fmt.Errorf("failed to calculate relative path: %w", err)
+		return &RelativePathCalculationError{Err: err}
 	}
 
 	// Create the symlink
-	if err := os.Symlink(relTarget, linkPath); err != nil {
-		return fmt.Errorf("failed to create symlink: %w", err)
-	}
-
-	return nil
+	return os.Symlink(relTarget, linkPath)
 }
 
 // MoveDirectory moves a directory from source to destination recursively
 func (fs *FileSystem) MoveDirectory(src, dst string) error {
-	// Check if source is a directory
-	info, err := os.Stat(src)
-	if err != nil {
-		return fmt.Errorf("failed to stat source: %w", err)
-	}
-
-	if !info.IsDir() {
-		return fmt.Errorf("source is not a directory: %s", src)
-	}
-
 	// Ensure destination parent directory exists
-	dstParent := filepath.Dir(dst)
-	if err := os.MkdirAll(dstParent, 0755); err != nil {
-		return fmt.Errorf("failed to create destination parent directory: %w", err)
+	if err := os.MkdirAll(filepath.Dir(dst), 0755); err != nil {
+		return &DirectoryCreationError{Operation: "destination parent directory", Err: err}
 	}
 
-	// Use os.Rename which works for directories
-	if err := os.Rename(src, dst); err != nil {
-		return fmt.Errorf("failed to move directory from %s to %s: %w", src, dst, err)
-	}
-
-	return nil
+	// Move the directory
+	return os.Rename(src, dst)
 }
diff --git a/internal/git/errors.go b/internal/git/errors.go
new file mode 100644
index 0000000..dba7929
--- /dev/null
+++ b/internal/git/errors.go
@@ -0,0 +1,218 @@
+package git
+
+import "fmt"
+
+// ANSI color codes for consistent formatting
+const (
+	colorReset  = "\033[0m"
+	colorBold   = "\033[1m"
+	colorGreen  = "\033[32m"
+	colorYellow = "\033[33m"
+)
+
+// formatError creates a consistently formatted error message with ❌ prefix
+func formatError(message string, args ...interface{}) string {
+	return fmt.Sprintf("❌ "+message, args...)
+}
+
+// formatURL formats a URL with styling
+func formatURL(url string) string {
+	return fmt.Sprintf("%s%s%s", colorBold, url, colorReset)
+}
+
+// formatRemote formats a remote name with styling
+func formatRemote(remote string) string {
+	return fmt.Sprintf("%s%s%s", colorGreen, remote, colorReset)
+}
+
+// GitInitError represents an error during git initialization
+type GitInitError struct {
+	Output string
+	Err    error
+}
+
+func (e *GitInitError) Error() string {
+	return formatError("Failed to initialize git repository. Please ensure git is installed and try again.")
+}
+
+func (e *GitInitError) Unwrap() error {
+	return e.Err
+}
+
+// BranchSetupError represents an error setting up the default branch
+type BranchSetupError struct {
+	Err error
+}
+
+func (e *BranchSetupError) Error() string {
+	return formatError("Failed to set up the default branch. Please check your git installation.")
+}
+
+func (e *BranchSetupError) Unwrap() error {
+	return e.Err
+}
+
+// RemoteExistsError represents an error when a remote already exists with different URL
+type RemoteExistsError struct {
+	Remote      string
+	ExistingURL string
+	NewURL      string
+}
+
+func (e *RemoteExistsError) Error() string {
+	return formatError("Remote %s is already configured with a different repository (%s). Cannot add %s.",
+		formatRemote(e.Remote), formatURL(e.ExistingURL), formatURL(e.NewURL))
+}
+
+func (e *RemoteExistsError) Unwrap() error {
+	return nil
+}
+
+// GitCommandError represents a generic git command execution error
+type GitCommandError struct {
+	Command string
+	Output  string
+	Err     error
+}
+
+func (e *GitCommandError) Error() string {
+	// Provide user-friendly messages based on common command types
+	switch e.Command {
+	case "add":
+		return formatError("Failed to stage files for commit. Please check file permissions and try again.")
+	case "commit":
+		return formatError("Failed to create commit. Please ensure you have staged changes and try again.")
+	case "remote add":
+		return formatError("Failed to add remote repository. Please check the repository URL and try again.")
+	case "rm":
+		return formatError("Failed to remove file from git tracking. Please check if the file exists and try again.")
+	case "log":
+		return formatError("Failed to retrieve commit history.")
+	case "remote":
+		return formatError("Failed to retrieve remote repository information.")
+	case "clone":
+		return formatError("Failed to clone repository. Please check the repository URL and your network connection.")
+	default:
+		return formatError("Git operation failed. Please check your repository state and try again.")
+	}
+}
+
+func (e *GitCommandError) Unwrap() error {
+	return e.Err
+}
+
+// NoRemoteError represents an error when no remote is configured
+type NoRemoteError struct{}
+
+func (e *NoRemoteError) Error() string {
+	return formatError("No remote repository is configured. Please add a remote repository first.")
+}
+
+func (e *NoRemoteError) Unwrap() error {
+	return nil
+}
+
+// RemoteNotFoundError represents an error when a specific remote is not found
+type RemoteNotFoundError struct {
+	Remote string
+	Err    error
+}
+
+func (e *RemoteNotFoundError) Error() string {
+	return formatError("Remote repository %s is not configured.", formatRemote(e.Remote))
+}
+
+func (e *RemoteNotFoundError) Unwrap() error {
+	return e.Err
+}
+
+// GitConfigError represents an error with git configuration
+type GitConfigError struct {
+	Setting string
+	Err     error
+}
+
+func (e *GitConfigError) Error() string {
+	return formatError("Failed to configure git settings. Please check your git installation.")
+}
+
+func (e *GitConfigError) Unwrap() error {
+	return e.Err
+}
+
+// UncommittedChangesError represents an error checking for uncommitted changes
+type UncommittedChangesError struct {
+	Err error
+}
+
+func (e *UncommittedChangesError) Error() string {
+	return formatError("Failed to check repository status. Please verify your git repository is valid.")
+}
+
+func (e *UncommittedChangesError) Unwrap() error {
+	return e.Err
+}
+
+// DirectoryRemovalError represents an error removing a directory
+type DirectoryRemovalError struct {
+	Path string
+	Err  error
+}
+
+func (e *DirectoryRemovalError) Error() string {
+	return formatError("Failed to prepare directory for operation. Please check directory permissions.")
+}
+
+func (e *DirectoryRemovalError) Unwrap() error {
+	return e.Err
+}
+
+// DirectoryCreationError represents an error creating a directory
+type DirectoryCreationError struct {
+	Path string
+	Err  error
+}
+
+func (e *DirectoryCreationError) Error() string {
+	return formatError("Failed to create directory. Please check permissions and available disk space.")
+}
+
+func (e *DirectoryCreationError) Unwrap() error {
+	return e.Err
+}
+
+// PushError represents an error during git push operation
+type PushError struct {
+	Reason string
+	Output string
+	Err    error
+}
+
+func (e *PushError) Error() string {
+	if e.Reason != "" {
+		return formatError("Cannot push changes: %s", e.Reason)
+	}
+	return formatError("Failed to push changes to remote repository. Please check your network connection and repository permissions.")
+}
+
+func (e *PushError) Unwrap() error {
+	return e.Err
+}
+
+// PullError represents an error during git pull operation
+type PullError struct {
+	Reason string
+	Output string
+	Err    error
+}
+
+func (e *PullError) Error() string {
+	if e.Reason != "" {
+		return formatError("Cannot pull changes: %s", e.Reason)
+	}
+	return formatError("Failed to pull changes from remote repository. Please check your network connection and resolve any conflicts.")
+}
+
+func (e *PullError) Unwrap() error {
+	return e.Err
+}
diff --git a/internal/git/git.go b/internal/git/git.go
index 7b3c2f3..1fbd8ce 100644
--- a/internal/git/git.go
+++ b/internal/git/git.go
@@ -34,7 +34,7 @@ func (g *Git) Init() error {
 
 		output, err := cmd.CombinedOutput()
 		if err != nil {
-			return fmt.Errorf("git init failed: %w\nOutput: %s", err, string(output))
+			return &GitInitError{Output: string(output), Err: err}
 		}
 
 		// Set the default branch to main
@@ -42,7 +42,7 @@ func (g *Git) Init() error {
 		cmd.Dir = g.repoPath
 
 		if err := cmd.Run(); err != nil {
-			return fmt.Errorf("failed to set default branch to main: %w", err)
+			return &BranchSetupError{Err: err}
 		}
 	}
 
@@ -60,7 +60,7 @@ func (g *Git) AddRemote(name, url string) error {
 			return nil
 		}
 		// Different URL, error
-		return fmt.Errorf("remote %s already exists with different URL: %s (trying to add: %s)", name, existingURL, url)
+		return &RemoteExistsError{Remote: name, ExistingURL: existingURL, NewURL: url}
 	}
 
 	// Remote doesn't exist, add it
@@ -69,7 +69,7 @@ func (g *Git) AddRemote(name, url string) error {
 
 	output, err := cmd.CombinedOutput()
 	if err != nil {
-		return fmt.Errorf("git remote add failed: %w\nOutput: %s", err, string(output))
+		return &GitCommandError{Command: "remote add", Output: string(output), Err: err}
 	}
 
 	return nil
@@ -164,7 +164,7 @@ func (g *Git) Add(filename string) error {
 
 	output, err := cmd.CombinedOutput()
 	if err != nil {
-		return fmt.Errorf("git add failed: %w\nOutput: %s", err, string(output))
+		return &GitCommandError{Command: "add", Output: string(output), Err: err}
 	}
 
 	return nil
@@ -189,7 +189,7 @@ func (g *Git) Remove(filename string) error {
 
 	output, err := cmd.CombinedOutput()
 	if err != nil {
-		return fmt.Errorf("git rm failed: %w\nOutput: %s", err, string(output))
+		return &GitCommandError{Command: "rm", Output: string(output), Err: err}
 	}
 
 	return nil
@@ -207,7 +207,7 @@ func (g *Git) Commit(message string) error {
 
 	output, err := cmd.CombinedOutput()
 	if err != nil {
-		return fmt.Errorf("git commit failed: %w\nOutput: %s", err, string(output))
+		return &GitCommandError{Command: "commit", Output: string(output), Err: err}
 	}
 
 	return nil
@@ -223,7 +223,7 @@ func (g *Git) ensureGitConfig() error {
 		cmd = exec.Command("git", "config", "user.name", "Lnk User")
 		cmd.Dir = g.repoPath
 		if err := cmd.Run(); err != nil {
-			return fmt.Errorf("failed to set git user.name: %w", err)
+			return &GitConfigError{Setting: "user.name", Err: err}
 		}
 	}
 
@@ -235,7 +235,7 @@ func (g *Git) ensureGitConfig() error {
 		cmd = exec.Command("git", "config", "user.email", "lnk@localhost")
 		cmd.Dir = g.repoPath
 		if err := cmd.Run(); err != nil {
-			return fmt.Errorf("failed to set git user.email: %w", err)
+			return &GitConfigError{Setting: "user.email", Err: err}
 		}
 	}
 
@@ -260,7 +260,7 @@ func (g *Git) GetCommits() ([]string, error) {
 		if strings.Contains(outputStr, "does not have any commits yet") {
 			return []string{}, nil
 		}
-		return nil, fmt.Errorf("git log failed: %w", err)
+		return nil, &GitCommandError{Command: "log", Output: outputStr, Err: err}
 	}
 
 	commits := strings.Split(strings.TrimSpace(string(output)), "\n")
@@ -282,18 +282,18 @@ func (g *Git) GetRemoteInfo() (string, error) {
 
 		output, err := cmd.Output()
 		if err != nil {
-			return "", fmt.Errorf("failed to list remotes: %w", err)
+			return "", &GitCommandError{Command: "remote", Output: string(output), Err: err}
 		}
 
 		remotes := strings.Split(strings.TrimSpace(string(output)), "\n")
 		if len(remotes) == 0 || remotes[0] == "" {
-			return "", fmt.Errorf("no remote configured")
+			return "", &NoRemoteError{}
 		}
 
 		// Use the first remote
 		url, err = g.getRemoteURL(remotes[0])
 		if err != nil {
-			return "", fmt.Errorf("failed to get remote URL: %w", err)
+			return "", &RemoteNotFoundError{Remote: remotes[0], Err: err}
 		}
 	}
 
@@ -319,7 +319,7 @@ func (g *Git) GetStatus() (*StatusInfo, error) {
 	// Check for uncommitted changes
 	dirty, err := g.HasChanges()
 	if err != nil {
-		return nil, fmt.Errorf("failed to check for uncommitted changes: %w", err)
+		return nil, &UncommittedChangesError{Err: err}
 	}
 
 	// Get the remote tracking branch
@@ -410,7 +410,7 @@ func (g *Git) HasChanges() (bool, error) {
 
 	output, err := cmd.Output()
 	if err != nil {
-		return false, fmt.Errorf("git status failed: %w", err)
+		return false, &GitCommandError{Command: "status", Output: string(output), Err: err}
 	}
 
 	return len(strings.TrimSpace(string(output))) > 0, nil
@@ -423,7 +423,7 @@ func (g *Git) AddAll() error {
 
 	output, err := cmd.CombinedOutput()
 	if err != nil {
-		return fmt.Errorf("git add failed: %w\nOutput: %s", err, string(output))
+		return &GitCommandError{Command: "add", Output: string(output), Err: err}
 	}
 
 	return nil
@@ -434,7 +434,7 @@ func (g *Git) Push() error {
 	// First ensure we have a remote configured
 	_, err := g.GetRemoteInfo()
 	if err != nil {
-		return fmt.Errorf("cannot push: %w", err)
+		return &PushError{Reason: err.Error(), Err: err}
 	}
 
 	cmd := exec.Command("git", "push", "-u", "origin", "main")
@@ -442,7 +442,7 @@ func (g *Git) Push() error {
 
 	output, err := cmd.CombinedOutput()
 	if err != nil {
-		return fmt.Errorf("git push failed: %w\nOutput: %s", err, string(output))
+		return &PushError{Output: string(output), Err: err}
 	}
 
 	return nil
@@ -453,7 +453,7 @@ func (g *Git) Pull() error {
 	// First ensure we have a remote configured
 	_, err := g.GetRemoteInfo()
 	if err != nil {
-		return fmt.Errorf("cannot pull: %w", err)
+		return &PullError{Reason: err.Error(), Err: err}
 	}
 
 	cmd := exec.Command("git", "pull", "origin", "main")
@@ -461,7 +461,7 @@ func (g *Git) Pull() error {
 
 	output, err := cmd.CombinedOutput()
 	if err != nil {
-		return fmt.Errorf("git pull failed: %w\nOutput: %s", err, string(output))
+		return &PullError{Output: string(output), Err: err}
 	}
 
 	return nil
@@ -471,20 +471,20 @@ func (g *Git) Pull() error {
 func (g *Git) Clone(url string) error {
 	// Remove the directory if it exists to ensure clean clone
 	if err := os.RemoveAll(g.repoPath); err != nil {
-		return fmt.Errorf("failed to remove existing directory: %w", err)
+		return &DirectoryRemovalError{Path: g.repoPath, Err: err}
 	}
 
 	// Create parent directory
 	parentDir := filepath.Dir(g.repoPath)
 	if err := os.MkdirAll(parentDir, 0755); err != nil {
-		return fmt.Errorf("failed to create parent directory: %w", err)
+		return &DirectoryCreationError{Path: parentDir, Err: err}
 	}
 
 	// Clone the repository
 	cmd := exec.Command("git", "clone", url, g.repoPath)
 	output, err := cmd.CombinedOutput()
 	if err != nil {
-		return fmt.Errorf("git clone failed: %w\nOutput: %s", err, string(output))
+		return &GitCommandError{Command: "clone", Output: string(output), Err: err}
 	}
 
 	// Set up upstream tracking for main branch