diff --git a/src/compiler/Nub.Lang/Frontend/Diagnostics/Diagnostics.cs b/src/compiler/Nub.Lang/Frontend/Diagnostics/Diagnostics.cs
new file mode 100644
index 0000000..f545764
--- /dev/null
+++ b/src/compiler/Nub.Lang/Frontend/Diagnostics/Diagnostics.cs
@@ -0,0 +1,376 @@
+using System.Text;
+using Nub.Lang.Frontend.Lexing;
+using Nub.Lang.Frontend.Parsing;
+
+namespace Nub.Lang.Frontend.Diagnostics;
+
+/// <summary>
+/// Represents a source location with line and column information
+/// </summary>
+public readonly struct SourceLocation(int line, int column, int index)
+{
+    public int Line { get; } = line;
+    public int Column { get; } = column;
+    public int Index { get; } = index;
+
+    public override string ToString() => $"{Line}:{Column}";
+}
+
+/// <summary>
+/// Represents a span of source code
+/// </summary>
+public readonly struct SourceSpan(SourceLocation start, SourceLocation end)
+{
+    public SourceLocation Start { get; } = start;
+    public SourceLocation End { get; } = end;
+
+    public override string ToString() => $"{Start}-{End}";
+}
+
+/// <summary>
+/// Severity levels for diagnostics
+/// </summary>
+public enum DiagnosticSeverity
+{
+    Info,
+    Warning,
+    Error
+}
+
+/// <summary>
+/// Represents a diagnostic message with source location
+/// </summary>
+public class Diagnostic
+{
+    public DiagnosticSeverity Severity { get; }
+    public string Message { get; }
+    public SourceFile SourceFile { get; }
+    public SourceSpan Span { get; }
+    public string? Help { get; }
+
+    public Diagnostic(DiagnosticSeverity severity, string message, SourceFile sourceFile,
+        SourceSpan span, string? help = null)
+    {
+        Severity = severity;
+        Message = message;
+        SourceFile = sourceFile;
+        Span = span;
+        Help = help;
+    }
+}
+
+/// <summary>
+/// Utility class for converting indices to line/column positions
+/// </summary>
+public static class SourceLocationCalculator
+{
+    /// <summary>
+    /// Convert a character index to line/column position
+    /// </summary>
+    public static SourceLocation IndexToLocation(string content, int index)
+    {
+        if (index < 0 || index > content.Length)
+            throw new ArgumentOutOfRangeException(nameof(index));
+
+        int line = 1;
+        int column = 1;
+
+        for (int i = 0; i < index && i < content.Length; i++)
+        {
+            if (content[i] == '\n')
+            {
+                line++;
+                column = 1;
+            }
+            else
+            {
+                column++;
+            }
+        }
+
+        return new SourceLocation(line, column, index);
+    }
+
+    /// <summary>
+    /// Get the source span for a token
+    /// </summary>
+    public static SourceSpan GetSpan(Token token)
+    {
+        var start = IndexToLocation(token.SourceFile.Content, token.StartIndex);
+        var end = IndexToLocation(token.SourceFile.Content, token.EndIndex);
+        return new SourceSpan(start, end);
+    }
+
+    /// <summary>
+    /// Get the source span for a node (from first to last token)
+    /// </summary>
+    public static SourceSpan GetSpan(Node node)
+    {
+        if (!node.Tokens.Any())
+            throw new ArgumentException("Node has no tokens");
+
+        var firstToken = node.Tokens.First();
+        var lastToken = node.Tokens.Last();
+
+        var start = IndexToLocation(firstToken.SourceFile.Content, firstToken.StartIndex);
+        var end = IndexToLocation(lastToken.SourceFile.Content, lastToken.EndIndex);
+
+        return new SourceSpan(start, end);
+    }
+}
+
+/// <summary>
+/// Builder for creating diagnostic messages
+/// </summary>
+public class DiagnosticBuilder
+{
+    private DiagnosticSeverity _severity;
+    private string _message = string.Empty;
+    private SourceFile _sourceFile;
+    private SourceSpan _span;
+    private string? _help;
+
+    public static DiagnosticBuilder Error(string message) =>
+        new() { _severity = DiagnosticSeverity.Error, _message = message };
+
+    public static DiagnosticBuilder Warning(string message) =>
+        new() { _severity = DiagnosticSeverity.Warning, _message = message };
+
+    public static DiagnosticBuilder Info(string message) =>
+        new() { _severity = DiagnosticSeverity.Info, _message = message };
+
+    public DiagnosticBuilder At(Token token)
+    {
+        _sourceFile = token.SourceFile;
+        _span = SourceLocationCalculator.GetSpan(token);
+        return this;
+    }
+
+    public DiagnosticBuilder At(Node node)
+    {
+        if (!node.Tokens.Any())
+            throw new ArgumentException("Node has no tokens");
+
+        _sourceFile = node.Tokens.First().SourceFile;
+        _span = SourceLocationCalculator.GetSpan(node);
+        return this;
+    }
+
+    public DiagnosticBuilder At(SourceFile sourceFile, SourceSpan span)
+    {
+        _sourceFile = sourceFile;
+        _span = span;
+        return this;
+    }
+
+    public DiagnosticBuilder WithHelp(string help)
+    {
+        _help = help;
+        return this;
+    }
+
+    public Diagnostic Build() => new(_severity, _message, _sourceFile, _span, _help);
+}
+
+/// <summary>
+/// Formats diagnostic messages for display
+/// </summary>
+public class DiagnosticFormatter
+{
+    private readonly DiagnosticFormatterOptions _options;
+
+    public DiagnosticFormatter(DiagnosticFormatterOptions? options = null)
+    {
+        _options = options ?? new DiagnosticFormatterOptions();
+    }
+
+    /// <summary>
+    /// Format a diagnostic as a string
+    /// </summary>
+    public string Format(Diagnostic diagnostic)
+    {
+        var sb = new StringBuilder();
+
+        // Header line: severity, location, and message
+        sb.Append(GetSeverityPrefix(diagnostic.Severity));
+        sb.Append($" at {diagnostic.SourceFile.Path}:{diagnostic.Span}: ");
+        sb.AppendLine(diagnostic.Message);
+
+        // Show source context
+        if (_options.ShowSourceContext)
+        {
+            AppendSourceContext(sb, diagnostic);
+        }
+
+        // Show help if available
+        if (!string.IsNullOrEmpty(diagnostic.Help))
+        {
+            sb.AppendLine();
+            sb.Append(_options.HelpPrefix);
+            sb.AppendLine(diagnostic.Help);
+        }
+
+        return sb.ToString();
+    }
+
+    /// <summary>
+    /// Format multiple diagnostics
+    /// </summary>
+    public string Format(IEnumerable<Diagnostic> diagnostics)
+    {
+        var sb = new StringBuilder();
+        var diagnosticList = diagnostics.ToList();
+
+        for (int i = 0; i < diagnosticList.Count; i++)
+        {
+            sb.Append(Format(diagnosticList[i]));
+
+            if (i < diagnosticList.Count - 1)
+            {
+                sb.AppendLine();
+                sb.AppendLine();
+            }
+        }
+
+        return sb.ToString();
+    }
+
+    private string GetSeverityPrefix(DiagnosticSeverity severity) => severity switch
+    {
+        DiagnosticSeverity.Error => _options.ErrorPrefix,
+        DiagnosticSeverity.Warning => _options.WarningPrefix,
+        DiagnosticSeverity.Info => _options.InfoPrefix,
+        _ => "diagnostic"
+    };
+
+    private void AppendSourceContext(StringBuilder sb, Diagnostic diagnostic)
+    {
+        var lines = diagnostic.SourceFile.Content.Split('\n');
+        var startLine = diagnostic.Span.Start.Line;
+        var endLine = diagnostic.Span.End.Line;
+
+        // Calculate line number width for padding
+        var maxLineNum = Math.Min(endLine + _options.ContextLines, lines.Length);
+        var lineNumWidth = maxLineNum.ToString().Length;
+
+        // Show context before error
+        var contextStart = Math.Max(1, startLine - _options.ContextLines);
+        for (int lineNum = contextStart; lineNum < startLine; lineNum++)
+        {
+            if (lineNum <= lines.Length)
+            {
+                sb.AppendLine($"{lineNum.ToString().PadLeft(lineNumWidth)} | {lines[lineNum - 1]}");
+            }
+        }
+
+        // Show error lines with highlighting
+        for (int lineNum = startLine; lineNum <= endLine && lineNum <= lines.Length; lineNum++)
+        {
+            var line = lines[lineNum - 1];
+            sb.AppendLine($"{lineNum.ToString().PadLeft(lineNumWidth)} | {line}");
+
+            // Add error indicators
+            if (_options.ShowErrorIndicators)
+            {
+                sb.Append(new string(' ', lineNumWidth + 3)); // Padding for line number + " | "
+
+                if (lineNum == startLine && lineNum == endLine)
+                {
+                    // Single line error
+                    var startCol = Math.Max(0, diagnostic.Span.Start.Column - 1);
+                    var endCol = Math.Min(line.Length, diagnostic.Span.End.Column - 1);
+                    var length = Math.Max(1, endCol - startCol);
+
+                    sb.Append(new string(' ', startCol));
+                    sb.AppendLine(new string(_options.ErrorIndicatorChar, length));
+                }
+                else if (lineNum == startLine)
+                {
+                    // First line of multi-line error
+                    var startCol = Math.Max(0, diagnostic.Span.Start.Column - 1);
+                    sb.Append(new string(' ', startCol));
+                    sb.AppendLine(new string(_options.ErrorIndicatorChar, line.Length - startCol));
+                }
+                else if (lineNum == endLine)
+                {
+                    // Last line of multi-line error
+                    var endCol = Math.Min(line.Length, diagnostic.Span.End.Column - 1);
+                    sb.AppendLine(new string(_options.ErrorIndicatorChar, endCol));
+                }
+                else
+                {
+                    // Middle line of multi-line error
+                    sb.AppendLine(new string(_options.ErrorIndicatorChar, line.Length));
+                }
+            }
+        }
+
+        // Show context after error
+        var contextEnd = Math.Min(lines.Length, endLine + _options.ContextLines);
+        for (int lineNum = endLine + 1; lineNum <= contextEnd; lineNum++)
+        {
+            if (lineNum <= lines.Length)
+            {
+                sb.AppendLine($"{lineNum.ToString().PadLeft(lineNumWidth)} | {lines[lineNum - 1]}");
+            }
+        }
+    }
+}
+
+/// <summary>
+/// Configuration options for diagnostic formatting
+/// </summary>
+public class DiagnosticFormatterOptions
+{
+    public string ErrorPrefix { get; set; } = "error";
+    public string WarningPrefix { get; set; } = "warning";
+    public string InfoPrefix { get; set; } = "info";
+    public string HelpPrefix { get; set; } = "help: ";
+
+    public bool ShowSourceContext { get; set; } = true;
+    public bool ShowErrorIndicators { get; set; } = true;
+    public char ErrorIndicatorChar { get; set; } = '^';
+    public int ContextLines { get; set; } = 2;
+}
+
+/// <summary>
+/// Extension methods for convenient error reporting
+/// </summary>
+public static class ErrorReportingExtensions
+{
+    /// <summary>
+    /// Create an error diagnostic for a token
+    /// </summary>
+    public static Diagnostic Error(this Token token, string message, string? help = null) =>
+        DiagnosticBuilder.Error(message).At(token).WithHelp(help).Build();
+
+    /// <summary>
+    /// Create a warning diagnostic for a token
+    /// </summary>
+    public static Diagnostic Warning(this Token token, string message, string? help = null) =>
+        DiagnosticBuilder.Warning(message).At(token).WithHelp(help).Build();
+
+    /// <summary>
+    /// Create an info diagnostic for a token
+    /// </summary>
+    public static Diagnostic Info(this Token token, string message, string? help = null) =>
+        DiagnosticBuilder.Info(message).At(token).WithHelp(help).Build();
+
+    /// <summary>
+    /// Create an error diagnostic for a node
+    /// </summary>
+    public static Diagnostic Error(this Node node, string message, string? help = null) =>
+        DiagnosticBuilder.Error(message).At(node).WithHelp(help).Build();
+
+    /// <summary>
+    /// Create a warning diagnostic for a node
+    /// </summary>
+    public static Diagnostic Warning(this Node node, string message, string? help = null) =>
+        DiagnosticBuilder.Warning(message).At(node).WithHelp(help).Build();
+
+    /// <summary>
+    /// Create an info diagnostic for a node
+    /// </summary>
+    public static Diagnostic Info(this Node node, string message, string? help = null) =>
+        DiagnosticBuilder.Info(message).At(node).WithHelp(help).Build();
+}
\ No newline at end of file
diff --git a/src/compiler/Nub.Lang/Frontend/Lexing/DocumentationToken.cs b/src/compiler/Nub.Lang/Frontend/Lexing/DocumentationToken.cs
index 422374b..4fb09f2 100644
--- a/src/compiler/Nub.Lang/Frontend/Lexing/DocumentationToken.cs
+++ b/src/compiler/Nub.Lang/Frontend/Lexing/DocumentationToken.cs
@@ -1,6 +1,6 @@
 namespace Nub.Lang.Frontend.Lexing;
 
-public class DocumentationToken(string filePath, int startIndex, int endIndex, string documentation) : Token(filePath, startIndex, endIndex)
+public class DocumentationToken(SourceFile sourceFile, int startIndex, int endIndex, string documentation) : Token(sourceFile, startIndex, endIndex)
 {
     public string Documentation { get; } = documentation;
 }
\ No newline at end of file
diff --git a/src/compiler/Nub.Lang/Frontend/Lexing/IdentifierToken.cs b/src/compiler/Nub.Lang/Frontend/Lexing/IdentifierToken.cs
index 92b37c7..077a802 100644
--- a/src/compiler/Nub.Lang/Frontend/Lexing/IdentifierToken.cs
+++ b/src/compiler/Nub.Lang/Frontend/Lexing/IdentifierToken.cs
@@ -1,6 +1,6 @@
 namespace Nub.Lang.Frontend.Lexing;
 
-public class IdentifierToken(string filePath, int startIndex, int endIndex, string value) : Token(filePath, startIndex, endIndex)
+public class IdentifierToken(SourceFile sourceFile, int startIndex, int endIndex, string value) : Token(sourceFile, startIndex, endIndex)
 {
     public string Value { get; } = value;
 }
\ No newline at end of file
diff --git a/src/compiler/Nub.Lang/Frontend/Lexing/Lexer.cs b/src/compiler/Nub.Lang/Frontend/Lexing/Lexer.cs
index e868073..7439c20 100644
--- a/src/compiler/Nub.Lang/Frontend/Lexing/Lexer.cs
+++ b/src/compiler/Nub.Lang/Frontend/Lexing/Lexer.cs
@@ -55,13 +55,13 @@ public class Lexer
     };
 
     private string _src = null!;
-    private string _filePath = null!;
+    private SourceFile _sourceFile;
     private int _index;
     
-    public List<Token> Lex(string src, string filePath)
+    public List<Token> Lex(string src, SourceFile sourceFile)
     {
         _src = src;
-        _filePath = filePath;
+        _sourceFile = sourceFile;
         _index = 0;
         
         List<Token> tokens = [];
@@ -121,7 +121,7 @@ public class Lexer
 
         if (documentation != null)
         {
-            return new DocumentationToken(_filePath, startIndex, _index, documentation);
+            return new DocumentationToken(_sourceFile, startIndex, _index, documentation);
         }
 
         ConsumeWhitespace();
@@ -144,20 +144,20 @@ public class Lexer
 
             if (Keywords.TryGetValue(buffer, out var keywordSymbol))
             {
-                return new SymbolToken(_filePath, startIndex, _index, keywordSymbol);
+                return new SymbolToken(_sourceFile, startIndex, _index, keywordSymbol);
             }
 
             if (Modifiers.TryGetValue(buffer, out var modifer))
             {
-                return new ModifierToken(_filePath, startIndex, _index, modifer);
+                return new ModifierToken(_sourceFile, startIndex, _index, modifer);
             }
 
             if (buffer is "true" or "false")
             {
-                return new LiteralToken(_filePath, startIndex, _index, NubPrimitiveType.Bool, buffer);
+                return new LiteralToken(_sourceFile, startIndex, _index, NubPrimitiveType.Bool, buffer);
             }
 
-            return new IdentifierToken(_filePath, startIndex, _index, buffer);
+            return new IdentifierToken(_sourceFile, startIndex, _index, buffer);
         }
 
         if (char.IsDigit(current))
@@ -195,7 +195,7 @@ public class Lexer
                 }
             }
 
-            return new LiteralToken(_filePath, startIndex, _index, isFloat ? NubPrimitiveType.F64 : NubPrimitiveType.I64, buffer);
+            return new LiteralToken(_sourceFile, startIndex, _index, isFloat ? NubPrimitiveType.F64 : NubPrimitiveType.I64, buffer);
         }
 
         // TODO: Revisit this
@@ -215,7 +215,7 @@ public class Lexer
                         Next();
                     }
 
-                    return new SymbolToken(_filePath, startIndex, _index, chain.Value);
+                    return new SymbolToken(_sourceFile, startIndex, _index, chain.Value);
                 }
             }
         }
@@ -223,7 +223,7 @@ public class Lexer
         if (Chars.TryGetValue(current, out var charSymbol))
         {
             Next();
-            return new SymbolToken(_filePath, startIndex, _index, charSymbol);
+            return new SymbolToken(_sourceFile, startIndex, _index, charSymbol);
         }
 
         if (current == '"')
@@ -248,7 +248,7 @@ public class Lexer
                 Next();
             }
 
-            return new LiteralToken(_filePath, startIndex, _index, NubPrimitiveType.String, buffer);
+            return new LiteralToken(_sourceFile, startIndex, _index, NubPrimitiveType.String, buffer);
         }
 
         throw new Exception($"Unknown character {current}");
diff --git a/src/compiler/Nub.Lang/Frontend/Lexing/LiteralToken.cs b/src/compiler/Nub.Lang/Frontend/Lexing/LiteralToken.cs
index 4797197..ddd734e 100644
--- a/src/compiler/Nub.Lang/Frontend/Lexing/LiteralToken.cs
+++ b/src/compiler/Nub.Lang/Frontend/Lexing/LiteralToken.cs
@@ -1,6 +1,6 @@
 namespace Nub.Lang.Frontend.Lexing;
 
-public class LiteralToken(string filePath, int startIndex, int endIndex, NubType type, string value) : Token(filePath, startIndex, endIndex)
+public class LiteralToken(SourceFile sourceFile, int startIndex, int endIndex, NubType type, string value) : Token(sourceFile, startIndex, endIndex)
 {
     public NubType Type { get; } = type;
     public string Value { get; } = value;
diff --git a/src/compiler/Nub.Lang/Frontend/Lexing/ModifierToken.cs b/src/compiler/Nub.Lang/Frontend/Lexing/ModifierToken.cs
index 0bc95fb..7927c21 100644
--- a/src/compiler/Nub.Lang/Frontend/Lexing/ModifierToken.cs
+++ b/src/compiler/Nub.Lang/Frontend/Lexing/ModifierToken.cs
@@ -1,6 +1,6 @@
 namespace Nub.Lang.Frontend.Lexing;
 
-public class ModifierToken(string filePath, int startIndex, int endIndex, Modifier modifier) : Token(filePath, startIndex, endIndex)
+public class ModifierToken(SourceFile sourceFile, int startIndex, int endIndex, Modifier modifier) : Token(sourceFile, startIndex, endIndex)
 {
     public Modifier Modifier { get; } = modifier;
 }
diff --git a/src/compiler/Nub.Lang/Frontend/Lexing/SymbolToken.cs b/src/compiler/Nub.Lang/Frontend/Lexing/SymbolToken.cs
index b1aa398..72a7331 100644
--- a/src/compiler/Nub.Lang/Frontend/Lexing/SymbolToken.cs
+++ b/src/compiler/Nub.Lang/Frontend/Lexing/SymbolToken.cs
@@ -1,6 +1,6 @@
 namespace Nub.Lang.Frontend.Lexing;
 
-public class SymbolToken(string filePath, int startIndex, int endIndex, Symbol symbol) : Token(filePath, startIndex, endIndex)
+public class SymbolToken(SourceFile sourceFile, int startIndex, int endIndex, Symbol symbol) : Token(sourceFile, startIndex, endIndex)
 {
     public Symbol Symbol { get; } = symbol;
 }
diff --git a/src/compiler/Nub.Lang/Frontend/Lexing/Token.cs b/src/compiler/Nub.Lang/Frontend/Lexing/Token.cs
index 154083f..ccf30b4 100644
--- a/src/compiler/Nub.Lang/Frontend/Lexing/Token.cs
+++ b/src/compiler/Nub.Lang/Frontend/Lexing/Token.cs
@@ -1,8 +1,8 @@
 namespace Nub.Lang.Frontend.Lexing;
 
-public abstract class Token(string filePath, int startIndex, int endIndex)
+public abstract class Token(SourceFile sourceFile, int startIndex, int endIndex)
 {
-    public string FilePath { get; } = filePath;
+    public SourceFile SourceFile { get; } = sourceFile;
     public int StartIndex { get; } = startIndex;
     public int EndIndex { get; } = endIndex;
 }
\ No newline at end of file
diff --git a/src/compiler/Nub.Lang/Program.cs b/src/compiler/Nub.Lang/Program.cs
index ede202f..ca697a6 100644
--- a/src/compiler/Nub.Lang/Program.cs
+++ b/src/compiler/Nub.Lang/Program.cs
@@ -69,7 +69,7 @@ internal static class Program
         foreach (var filePath in filePaths)
         {
             var src = File.ReadAllText(filePath);
-            tokens.AddRange(Lexer.Lex(src, filePath));
+            tokens.AddRange(Lexer.Lex(src, new SourceFile(filePath, src)));
         }
 
         var module = Parser.ParseModule(tokens, rootFilePath);
diff --git a/src/compiler/Nub.Lang/SourceFile.cs b/src/compiler/Nub.Lang/SourceFile.cs
new file mode 100644
index 0000000..b5b2271
--- /dev/null
+++ b/src/compiler/Nub.Lang/SourceFile.cs
@@ -0,0 +1,7 @@
+namespace Nub.Lang;
+
+public readonly struct SourceFile(string path, string content)
+{
+    public string Path { get; } = path;
+    public string Content { get; } = content;
+}