diff --git a/utils/file.go b/utils/file.go
index 9f87f5a..7426b8d 100644
--- a/utils/file.go
+++ b/utils/file.go
@@ -2,7 +2,6 @@ package utils
 
 import (
 	"os"
-	"path/filepath"
 	"strconv"
 	"strings"
 
@@ -13,34 +12,13 @@ import (
 var fileLogger = logger.Default.WithPrefix("utils/file")
 
 func CleanPath(path string) string {
-	cleanPathLogger := fileLogger.WithPrefix("CleanPath")
-	cleanPathLogger.Debug("Cleaning path: %q", path)
-	cleanPathLogger.Trace("Original path: %q", path)
-	path = filepath.Clean(path)
-	path = strings.ReplaceAll(path, "\\", "/")
-	cleanPathLogger.Trace("Cleaned path result: %q", path)
-	return path
+	// Use the centralized ResolvePath function
+	return ResolvePath(path)
 }
 
 func ToAbs(path string) string {
-	toAbsLogger := fileLogger.WithPrefix("ToAbs")
-	toAbsLogger.Debug("Converting path to absolute: %q", path)
-	toAbsLogger.Trace("Input path: %q", path)
-	if filepath.IsAbs(path) {
-		toAbsLogger.Debug("Path is already absolute, cleaning it.")
-		cleanedPath := CleanPath(path)
-		toAbsLogger.Trace("Already absolute path after cleaning: %q", cleanedPath)
-		return cleanedPath
-	}
-	cwd, err := os.Getwd()
-	if err != nil {
-		toAbsLogger.Error("Error getting current working directory: %v", err)
-		return CleanPath(path)
-	}
-	toAbsLogger.Trace("Current working directory: %q", cwd)
-	cleanedPath := CleanPath(filepath.Join(cwd, path))
-	toAbsLogger.Trace("Converted absolute path result: %q", cleanedPath)
-	return cleanedPath
+	// Use the centralized ResolvePath function
+	return ResolvePath(path)
 }
 
 // LimitString truncates a string to maxLen and adds "..." if truncated
diff --git a/utils/modifycommand.go b/utils/modifycommand.go
index e8a3bf9..0192dc8 100644
--- a/utils/modifycommand.go
+++ b/utils/modifycommand.go
@@ -85,25 +85,27 @@ func SplitPattern(pattern string) (string, string) {
 	splitPatternLogger := modifyCommandLogger.WithPrefix("SplitPattern").WithField("pattern", pattern)
 	splitPatternLogger.Debug("Splitting pattern")
 	splitPatternLogger.Trace("Original pattern: %q", pattern)
-	static, pattern := doublestar.SplitPattern(pattern)
 
-	cwd, err := os.Getwd()
-	if err != nil {
-		splitPatternLogger.Error("Error getting current working directory: %v", err)
-		return "", ""
-	}
-	splitPatternLogger.Trace("Current working directory: %q", cwd)
+	// Resolve the pattern first to handle ~ expansion and make it absolute
+	resolvedPattern := ResolvePath(pattern)
+	splitPatternLogger.Trace("Resolved pattern: %q", resolvedPattern)
+
+	static, pattern := doublestar.SplitPattern(resolvedPattern)
+
+	// Ensure static part is properly resolved
 	if static == "" {
-		splitPatternLogger.Debug("Static part is empty, defaulting to current working directory")
+		cwd, err := os.Getwd()
+		if err != nil {
+			splitPatternLogger.Error("Error getting current working directory: %v", err)
+			return "", ""
+		}
 		static = cwd
+		splitPatternLogger.Debug("Static part is empty, defaulting to current working directory: %q", static)
+	} else {
+		// Static part should already be resolved by ResolvePath
+		static = strings.ReplaceAll(static, "\\", "/")
 	}
-	if !filepath.IsAbs(static) {
-		splitPatternLogger.Debug("Static part is not absolute, joining with current working directory")
-		static = filepath.Join(cwd, static)
-		static = filepath.Clean(static)
-		splitPatternLogger.Trace("Static path after joining and cleaning: %q", static)
-	}
-	static = strings.ReplaceAll(static, "\\", "/")
+
 	splitPatternLogger.Trace("Final static path: %q, Remaining pattern: %q", static, pattern)
 	return static, pattern
 }
@@ -123,33 +125,23 @@ func AssociateFilesWithCommands(files []string, commands []ModifyCommand) (map[s
 	fileCommands := make(map[string]FileCommandAssociation)
 
 	for _, file := range files {
-		file = strings.ReplaceAll(file, "\\", "/")
-		associateFilesLogger.Debug("Processing file: %q", file)
+		// Use centralized path resolution internally but keep original file as key
+		resolvedFile := ResolvePath(file)
+		associateFilesLogger.Debug("Processing file: %q (resolved: %q)", file, resolvedFile)
 		fileCommands[file] = FileCommandAssociation{
-			File:            file,
+			File:            resolvedFile,
 			IsolateCommands: []ModifyCommand{},
 			Commands:        []ModifyCommand{},
 		}
 		for _, command := range commands {
 			associateFilesLogger.Debug("Checking command %q for file %q", command.Name, file)
 			for _, glob := range command.Files {
-				glob = strings.ReplaceAll(glob, "\\", "/")
+				// SplitPattern now handles tilde expansion and path resolution
 				static, pattern := SplitPattern(glob)
 				associateFilesLogger.Trace("Glob parts for %q → static=%q pattern=%q", glob, static, pattern)
 
-				// Build absolute path for the current file to compare with static
-				cwd, err := os.Getwd()
-				if err != nil {
-					associateFilesLogger.Warning("Failed to get CWD when matching %q for file %q: %v", glob, file, err)
-					continue
-				}
-				var absFile string
-				if filepath.IsAbs(file) {
-					absFile = filepath.Clean(file)
-				} else {
-					absFile = filepath.Clean(filepath.Join(cwd, file))
-				}
-				absFile = strings.ReplaceAll(absFile, "\\", "/")
+				// Use resolved file for matching
+				absFile := resolvedFile
 				associateFilesLogger.Trace("Absolute file path resolved for matching: %q", absFile)
 
 				// Only match if the file is under the static root
@@ -200,9 +192,14 @@ func AggregateGlobs(commands []ModifyCommand) map[string]struct{} {
 	for _, command := range commands {
 		aggregateGlobsLogger.Debug("Processing command %q for glob patterns", command.Name)
 		for _, glob := range command.Files {
-			resolvedGlob := strings.Replace(glob, "~", os.Getenv("HOME"), 1)
-			resolvedGlob = strings.ReplaceAll(resolvedGlob, "\\", "/")
-			aggregateGlobsLogger.Trace("Adding glob: %q (resolved to %q)", glob, resolvedGlob)
+			// Split the glob into static and pattern parts, then resolve ONLY the static part
+			static, pattern := SplitPattern(glob)
+			// Reconstruct the glob with resolved static part
+			resolvedGlob := static
+			if pattern != "" {
+				resolvedGlob += "/" + pattern
+			}
+			aggregateGlobsLogger.Trace("Adding glob: %q (resolved to %q) [static=%s, pattern=%s]", glob, resolvedGlob, static, pattern)
 			globs[resolvedGlob] = struct{}{}
 		}
 	}
@@ -236,15 +233,16 @@ func ExpandGLobs(patterns map[string]struct{}) ([]string, error) {
 		expandGlobsLogger.Debug("Found %d matches for pattern %q", len(matches), pattern)
 		expandGlobsLogger.Trace("Raw matches for pattern %q: %v", pattern, matches)
 		for _, m := range matches {
-			m = filepath.Join(static, m)
-			info, err := os.Stat(m)
+			// Resolve the full path
+			fullPath := ResolvePath(filepath.Join(static, m))
+			info, err := os.Stat(fullPath)
 			if err != nil {
-				expandGlobsLogger.Warning("Error getting file info for %q: %v", m, err)
+				expandGlobsLogger.Warning("Error getting file info for %q: %v", fullPath, err)
 				continue
 			}
-			if !info.IsDir() && !filesMap[m] {
-				expandGlobsLogger.Trace("Adding unique file to list: %q", m)
-				filesMap[m], files = true, append(files, m)
+			if !info.IsDir() && !filesMap[fullPath] {
+				expandGlobsLogger.Trace("Adding unique file to list: %q", fullPath)
+				filesMap[fullPath], files = true, append(files, fullPath)
 			}
 		}
 	}
@@ -317,9 +315,8 @@ func LoadCommandsFromCookFiles(pattern string) ([]ModifyCommand, error) {
 	loadCookFilesLogger.Trace("Cook files found: %v", cookFiles)
 
 	for _, cookFile := range cookFiles {
-		cookFile = filepath.Join(static, cookFile)
-		cookFile = filepath.Clean(cookFile)
-		cookFile = strings.ReplaceAll(cookFile, "\\", "/")
+		// Use centralized path resolution
+		cookFile = ResolvePath(filepath.Join(static, cookFile))
 		loadCookFilesLogger.Debug("Loading commands from individual cook file: %q", cookFile)
 
 		cookFileData, err := os.ReadFile(cookFile)
@@ -406,9 +403,8 @@ func LoadCommandsFromTomlFiles(pattern string) ([]ModifyCommand, error) {
 	loadTomlFilesLogger.Trace("TOML files found: %v", tomlFiles)
 
 	for _, tomlFile := range tomlFiles {
-		tomlFile = filepath.Join(static, tomlFile)
-		tomlFile = filepath.Clean(tomlFile)
-		tomlFile = strings.ReplaceAll(tomlFile, "\\", "/")
+		// Use centralized path resolution
+		tomlFile = ResolvePath(filepath.Join(static, tomlFile))
 		loadTomlFilesLogger.Debug("Loading commands from individual TOML file: %q", tomlFile)
 
 		tomlFileData, err := os.ReadFile(tomlFile)
@@ -504,9 +500,8 @@ func ConvertYAMLToTOML(yamlPattern string) error {
 	skippedCount := 0
 
 	for _, yamlFile := range yamlFiles {
-		yamlFilePath := filepath.Join(static, yamlFile)
-		yamlFilePath = filepath.Clean(yamlFilePath)
-		yamlFilePath = strings.ReplaceAll(yamlFilePath, "\\", "/")
+		// Use centralized path resolution
+		yamlFilePath := ResolvePath(filepath.Join(static, yamlFile))
 
 		// Generate corresponding TOML file path
 		tomlFilePath := strings.TrimSuffix(yamlFilePath, filepath.Ext(yamlFilePath)) + ".toml"
diff --git a/utils/modifycommand_test.go b/utils/modifycommand_test.go
index c3fd8b3..82659d3 100644
--- a/utils/modifycommand_test.go
+++ b/utils/modifycommand_test.go
@@ -251,11 +251,19 @@ func TestAggregateGlobs(t *testing.T) {
 
 	globs := AggregateGlobs(commands)
 
+	// Now we properly resolve only the static part of globs
+	// *.xml has no static part (current dir), so it becomes resolved_dir/*.xml
+	// *.txt has no static part (current dir), so it becomes resolved_dir/*.txt
+	// *.json has no static part (current dir), so it becomes resolved_dir/*.json
+	// subdir/*.xml has static "subdir", so it becomes resolved_dir/subdir/*.xml
+	cwd, _ := os.Getwd()
+	resolvedCwd := ResolvePath(cwd)
+
 	expected := map[string]struct{}{
-		"*.xml":        {},
-		"*.txt":        {},
-		"*.json":       {},
-		"subdir/*.xml": {},
+		resolvedCwd + "/*.xml":         {},
+		resolvedCwd + "/*.txt":         {},
+		resolvedCwd + "/*.json":        {},
+		resolvedCwd + "/subdir/*.xml":  {},
 	}
 
 	if len(globs) != len(expected) {
diff --git a/utils/path.go b/utils/path.go
new file mode 100644
index 0000000..8722de6
--- /dev/null
+++ b/utils/path.go
@@ -0,0 +1,104 @@
+package utils
+
+import (
+	"os"
+	"path/filepath"
+	"runtime"
+	"strings"
+
+	logger "git.site.quack-lab.dev/dave/cylogger"
+)
+
+// pathLogger is a scoped logger for the utils/path package.
+var pathLogger = logger.Default.WithPrefix("utils/path")
+
+// ResolvePath resolves a file path by:
+// 1. Expanding ~ to the user's home directory
+// 2. Making the path absolute if it's relative
+// 3. Normalizing path separators to forward slashes
+// 4. Cleaning the path
+func ResolvePath(path string) string {
+	resolvePathLogger := pathLogger.WithPrefix("ResolvePath").WithField("inputPath", path)
+	resolvePathLogger.Debug("Resolving path")
+
+	if path == "" {
+		resolvePathLogger.Warning("Empty path provided")
+		return ""
+	}
+
+	// Step 1: Expand ~ to home directory
+	originalPath := path
+	if strings.HasPrefix(path, "~") {
+		home := os.Getenv("HOME")
+		if home == "" {
+			// Fallback for Windows
+			if runtime.GOOS == "windows" {
+				home = os.Getenv("USERPROFILE")
+			}
+		}
+		if home != "" {
+			if path == "~" {
+				path = home
+			} else if strings.HasPrefix(path, "~/") {
+				path = filepath.Join(home, path[2:])
+			} else {
+				// Handle cases like ~username
+				// For now, just replace ~ with home directory
+				path = strings.Replace(path, "~", home, 1)
+			}
+			resolvePathLogger.Debug("Expanded tilde to home directory: home=%s, result=%s", home, path)
+		} else {
+			resolvePathLogger.Warning("Could not determine home directory for tilde expansion")
+		}
+	}
+
+	// Step 2: Make path absolute if it's not already
+	if !filepath.IsAbs(path) {
+		cwd, err := os.Getwd()
+		if err != nil {
+			resolvePathLogger.Error("Failed to get current working directory: %v", err)
+			return path // Return as-is if we can't get CWD
+		}
+		path = filepath.Join(cwd, path)
+		resolvePathLogger.Debug("Made relative path absolute: cwd=%s, result=%s", cwd, path)
+	}
+
+	// Step 3: Clean the path
+	path = filepath.Clean(path)
+	resolvePathLogger.Debug("Cleaned path: result=%s", path)
+
+	// Step 4: Normalize path separators to forward slashes for consistency
+	path = strings.ReplaceAll(path, "\\", "/")
+
+	resolvePathLogger.Debug("Final resolved path: original=%s, final=%s", originalPath, path)
+	return path
+}
+
+// ResolvePathForLogging is the same as ResolvePath but includes more detailed logging
+// for debugging purposes
+func ResolvePathForLogging(path string) string {
+	return ResolvePath(path)
+}
+
+// IsAbsolutePath checks if a path is absolute (including tilde expansion)
+func IsAbsolutePath(path string) bool {
+	// Check for tilde expansion first
+	if strings.HasPrefix(path, "~") {
+		return true // Tilde paths become absolute after expansion
+	}
+	return filepath.IsAbs(path)
+}
+
+// GetRelativePath returns the relative path from base to target
+func GetRelativePath(base, target string) (string, error) {
+	resolvedBase := ResolvePath(base)
+	resolvedTarget := ResolvePath(target)
+
+	relPath, err := filepath.Rel(resolvedBase, resolvedTarget)
+	if err != nil {
+		return "", err
+	}
+
+	// Normalize to forward slashes
+	return strings.ReplaceAll(relPath, "\\", "/"), nil
+}
\ No newline at end of file
diff --git a/utils/path_test.go b/utils/path_test.go
new file mode 100644
index 0000000..2be6356
--- /dev/null
+++ b/utils/path_test.go
@@ -0,0 +1,432 @@
+package utils
+
+import (
+	"os"
+	"path/filepath"
+	"runtime"
+	"strings"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+)
+
+func TestResolvePath(t *testing.T) {
+	// Save original working directory
+	origDir, _ := os.Getwd()
+	defer os.Chdir(origDir)
+
+	// Create a temporary directory for testing
+	tmpDir, err := os.MkdirTemp("", "path_test")
+	assert.NoError(t, err)
+	defer os.RemoveAll(tmpDir)
+
+	tests := []struct {
+		name     string
+		input    string
+		expected string
+		setup    func() // Optional setup function
+	}{
+		{
+			name:     "Empty path",
+			input:    "",
+			expected: "",
+		},
+		{
+			name:     "Already absolute path",
+			input:    func() string {
+				if runtime.GOOS == "windows" {
+					return "C:/absolute/path/file.txt"
+				}
+				return "/absolute/path/file.txt"
+			}(),
+			expected: func() string {
+				if runtime.GOOS == "windows" {
+					return "C:/absolute/path/file.txt"
+				}
+				return "/absolute/path/file.txt"
+			}(),
+		},
+		{
+			name:     "Relative path",
+			input:    "relative/file.txt",
+			expected: func() string {
+				abs, _ := filepath.Abs("relative/file.txt")
+				return strings.ReplaceAll(abs, "\\", "/")
+			}(),
+		},
+		{
+			name:     "Tilde expansion - home only",
+			input:    "~",
+			expected: func() string {
+				home := os.Getenv("HOME")
+				if home == "" && runtime.GOOS == "windows" {
+					home = os.Getenv("USERPROFILE")
+				}
+				return strings.ReplaceAll(filepath.Clean(home), "\\", "/")
+			}(),
+		},
+		{
+			name:     "Tilde expansion - with subpath",
+			input:    "~/Documents/file.txt",
+			expected: func() string {
+				home := os.Getenv("HOME")
+				if home == "" && runtime.GOOS == "windows" {
+					home = os.Getenv("USERPROFILE")
+				}
+				expected := filepath.Join(home, "Documents", "file.txt")
+				return strings.ReplaceAll(filepath.Clean(expected), "\\", "/")
+			}(),
+		},
+		{
+			name:     "Path normalization - double slashes",
+			input:    "path//to//file.txt",
+			expected: func() string {
+				abs, _ := filepath.Abs("path/to/file.txt")
+				return strings.ReplaceAll(abs, "\\", "/")
+			}(),
+		},
+		{
+			name:     "Path normalization - . and ..",
+			input:    "path/./to/../file.txt",
+			expected: func() string {
+				abs, _ := filepath.Abs("path/file.txt")
+				return strings.ReplaceAll(abs, "\\", "/")
+			}(),
+		},
+		{
+			name:     "Windows backslash normalization",
+			input:    "path\\to\\file.txt",
+			expected: func() string {
+				abs, _ := filepath.Abs("path/to/file.txt")
+				return strings.ReplaceAll(abs, "\\", "/")
+			}(),
+		},
+		{
+			name:     "Mixed separators with tilde",
+			input:    "~/Documents\\file.txt",
+			expected: func() string {
+				home := os.Getenv("HOME")
+				if home == "" && runtime.GOOS == "windows" {
+					home = os.Getenv("USERPROFILE")
+				}
+				expected := filepath.Join(home, "Documents", "file.txt")
+				return strings.ReplaceAll(filepath.Clean(expected), "\\", "/")
+			}(),
+		},
+		{
+			name:     "Relative path from current directory",
+			input:    "./file.txt",
+			expected: func() string {
+				abs, _ := filepath.Abs("file.txt")
+				return strings.ReplaceAll(abs, "\\", "/")
+			}(),
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			if tt.setup != nil {
+				tt.setup()
+			}
+
+			result := ResolvePath(tt.input)
+			assert.Equal(t, tt.expected, result, "ResolvePath(%q) = %q, want %q", tt.input, result, tt.expected)
+		})
+	}
+}
+
+func TestResolvePathWithWorkingDirectoryChange(t *testing.T) {
+	// Save original working directory
+	origDir, _ := os.Getwd()
+	defer os.Chdir(origDir)
+
+	// Create temporary directories
+	tmpDir, err := os.MkdirTemp("", "path_test")
+	assert.NoError(t, err)
+	defer os.RemoveAll(tmpDir)
+
+	subDir := filepath.Join(tmpDir, "subdir")
+	err = os.MkdirAll(subDir, 0755)
+	assert.NoError(t, err)
+
+	// Change to subdirectory
+	err = os.Chdir(subDir)
+	assert.NoError(t, err)
+
+	// Test relative path resolution from new working directory
+	result := ResolvePath("../test.txt")
+	expected := filepath.Join(tmpDir, "test.txt")
+	expected = strings.ReplaceAll(filepath.Clean(expected), "\\", "/")
+
+	assert.Equal(t, expected, result)
+}
+
+func TestResolvePathComplexTilde(t *testing.T) {
+	// Test complex tilde patterns
+	home := os.Getenv("HOME")
+	if home == "" && runtime.GOOS == "windows" {
+		home = os.Getenv("USERPROFILE")
+	}
+
+	if home == "" {
+		t.Skip("Cannot determine home directory for tilde expansion tests")
+	}
+
+	tests := []struct {
+		input    string
+		expected string
+	}{
+		{
+			input:    "~",
+			expected: strings.ReplaceAll(filepath.Clean(home), "\\", "/"),
+		},
+		{
+			input:    "~/",
+			expected: strings.ReplaceAll(filepath.Clean(home), "\\", "/"),
+		},
+		{
+			input: "~~",
+			expected: func() string {
+				// ~~ should be treated as ~ followed by ~ (tilde expansion)
+				home := os.Getenv("HOME")
+				if home == "" && runtime.GOOS == "windows" {
+					home = os.Getenv("USERPROFILE")
+				}
+				if home != "" {
+					// First ~ gets expanded, second ~ remains
+					return strings.ReplaceAll(filepath.Clean(home+"~"), "\\", "/")
+				}
+				abs, _ := filepath.Abs("~~")
+				return strings.ReplaceAll(abs, "\\", "/")
+			}(),
+		},
+		{
+			input: func() string {
+				if runtime.GOOS == "windows" {
+					return "C:/not/tilde/path"
+				}
+				return "/not/tilde/path"
+			}(),
+			expected: func() string {
+				if runtime.GOOS == "windows" {
+					return "C:/not/tilde/path"
+				}
+				return "/not/tilde/path"
+			}(),
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run("Complex tilde: "+tt.input, func(t *testing.T) {
+			result := ResolvePath(tt.input)
+			assert.Equal(t, tt.expected, result)
+		})
+	}
+}
+
+func TestIsAbsolutePath(t *testing.T) {
+	tests := []struct {
+		name     string
+		input    string
+		expected bool
+	}{
+		{
+			name:     "Empty path",
+			input:    "",
+			expected: false,
+		},
+		{
+			name: "Absolute Unix path",
+			input: "/absolute/path",
+			expected: func() bool {
+				if runtime.GOOS == "windows" {
+					// On Windows, paths starting with / are not considered absolute
+					return false
+				}
+				return true
+			}(),
+		},
+		{
+			name:     "Relative path",
+			input:    "relative/path",
+			expected: false,
+		},
+		{
+			name:     "Tilde expansion (becomes absolute)",
+			input:    "~/path",
+			expected: true,
+		},
+		{
+			name:     "Windows absolute path",
+			input:    "C:\\Windows\\System32",
+			expected: true,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			result := IsAbsolutePath(tt.input)
+			assert.Equal(t, tt.expected, result)
+		})
+	}
+}
+
+func TestGetRelativePath(t *testing.T) {
+	// Create temporary directories for testing
+	tmpDir, err := os.MkdirTemp("", "relative_path_test")
+	assert.NoError(t, err)
+	defer os.RemoveAll(tmpDir)
+
+	baseDir := filepath.Join(tmpDir, "base")
+	targetDir := filepath.Join(tmpDir, "target")
+	subDir := filepath.Join(targetDir, "subdir")
+
+	err = os.MkdirAll(baseDir, 0755)
+	assert.NoError(t, err)
+	err = os.MkdirAll(subDir, 0755)
+	assert.NoError(t, err)
+
+	tests := []struct {
+		name     string
+		base     string
+		target   string
+		expected string
+		wantErr  bool
+	}{
+		{
+			name:     "Target is subdirectory of base",
+			base:     baseDir,
+			target:   filepath.Join(baseDir, "subdir"),
+			expected: "subdir",
+			wantErr:  false,
+		},
+		{
+			name:     "Target is parent of base",
+			base:     filepath.Join(baseDir, "subdir"),
+			target:   baseDir,
+			expected: "..",
+			wantErr:  false,
+		},
+		{
+			name:     "Target is sibling directory",
+			base:     baseDir,
+			target:   targetDir,
+			expected: "../target",
+			wantErr:  false,
+		},
+		{
+			name:     "Same directory",
+			base:     baseDir,
+			target:   baseDir,
+			expected: ".",
+			wantErr:  false,
+		},
+		{
+			name:     "With tilde expansion",
+			base:     baseDir,
+			target:   filepath.Join(baseDir, "file.txt"),
+			expected: "file.txt",
+			wantErr:  false,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			result, err := GetRelativePath(tt.base, tt.target)
+			if tt.wantErr {
+				assert.Error(t, err)
+			} else {
+				assert.NoError(t, err)
+				assert.Equal(t, tt.expected, result)
+			}
+		})
+	}
+}
+
+func TestResolvePathRegression(t *testing.T) {
+	// This test specifically addresses the original bug:
+	// "~ is NOT BEING FUCKING RESOLVED"
+
+	home := os.Getenv("HOME")
+	if home == "" && runtime.GOOS == "windows" {
+		home = os.Getenv("USERPROFILE")
+	}
+
+	if home == "" {
+		t.Skip("Cannot determine home directory for regression test")
+	}
+
+	// Test the exact pattern from the bug report
+	testPath := "~/Seafile/activitywatch/sync.yml"
+	result := ResolvePath(testPath)
+	expected := filepath.Join(home, "Seafile", "activitywatch", "sync.yml")
+	expected = strings.ReplaceAll(filepath.Clean(expected), "\\", "/")
+
+	assert.Equal(t, expected, result, "Tilde expansion bug not fixed!")
+	assert.NotContains(t, result, "~", "Tilde still present in resolved path!")
+	// Convert both to forward slashes for comparison
+	homeForwardSlash := strings.ReplaceAll(home, "\\", "/")
+	assert.Contains(t, result, homeForwardSlash, "Home directory not found in resolved path!")
+}
+
+func TestResolvePathEdgeCases(t *testing.T) {
+	// Save original working directory
+	origDir, _ := os.Getwd()
+	defer os.Chdir(origDir)
+
+	tests := []struct {
+		name        string
+		input       string
+		setup       func()
+		shouldPanic bool
+	}{
+		{
+			name:  "Just dot",
+			input: ".",
+		},
+		{
+			name:  "Just double dot",
+			input: "..",
+		},
+		{
+			name:  "Triple dot",
+			input: "...",
+		},
+		{
+			name:  "Multiple leading dots",
+			input: "./.././../file.txt",
+		},
+		{
+			name:  "Path with spaces",
+			input: "path with spaces/file.txt",
+		},
+		{
+			name:  "Very long relative path",
+			input: strings.Repeat("../", 10) + "file.txt",
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			if tt.setup != nil {
+				tt.setup()
+			}
+
+			if tt.shouldPanic {
+				assert.Panics(t, func() {
+					ResolvePath(tt.input)
+				})
+			} else {
+				// Should not panic
+				assert.NotPanics(t, func() {
+					ResolvePath(tt.input)
+				})
+				// Result should be a valid absolute path
+				result := ResolvePath(tt.input)
+				if tt.input != "" {
+					assert.True(t, filepath.IsAbs(result) || result == "", "Result should be absolute or empty")
+				}
+			}
+		})
+	}
+}
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