diff --git a/DuplicatePathChecker.cs b/DuplicatePathChecker.cs
new file mode 100644
index 0000000..75f4be4
--- /dev/null
+++ b/DuplicatePathChecker.cs
@@ -0,0 +1,18 @@
+using System;
+
+namespace PathCleaner
+{
+    class DuplicatePathChecker : IPathChecker
+    {
+        public string Reason
+        {
+            get { return "Duplicate"; }
+        }
+
+        public bool Identify(string folder, string previousFolder)
+        {
+            return previousFolder != null 
+                && String.Compare(folder, previousFolder, StringComparison.InvariantCultureIgnoreCase) == 0;
+        }
+    }
+}
diff --git a/EmptyPathChecker.cs b/EmptyPathChecker.cs
new file mode 100644
index 0000000..0799c00
--- /dev/null
+++ b/EmptyPathChecker.cs
@@ -0,0 +1,19 @@
+using System.IO;
+using System.Linq;
+
+namespace PathCleaner
+{
+    class EmptyPathChecker : IPathChecker
+    {
+        public string Reason
+        {
+            get { return "Empty"; }
+        }
+
+        public bool Identify(string folder, string previousFolder)
+        {
+            return !Directory.EnumerateFiles(folder).Any();
+        }
+    }
+
+}
diff --git a/IPathChecker.cs b/IPathChecker.cs
new file mode 100644
index 0000000..6832b61
--- /dev/null
+++ b/IPathChecker.cs
@@ -0,0 +1,9 @@
+namespace PathCleaner
+{
+    interface IPathChecker
+    {
+        string Reason { get; }
+        bool Identify(string folder, string previousFolder);
+    }
+
+}
diff --git a/MissingPathChecker.cs b/MissingPathChecker.cs
new file mode 100644
index 0000000..ed23d36
--- /dev/null
+++ b/MissingPathChecker.cs
@@ -0,0 +1,18 @@
+using System.IO;
+
+namespace PathCleaner
+{
+    class MissingPathChecker : IPathChecker
+    {
+        public string Reason
+        {
+            get { return "Missing"; }
+        }
+
+        public bool Identify(string folder, string previousFolder)
+        {
+            return !Directory.Exists(folder);
+        }
+    }
+
+}
diff --git a/NoExecutablesPathChecker.cs b/NoExecutablesPathChecker.cs
new file mode 100644
index 0000000..b5fc980
--- /dev/null
+++ b/NoExecutablesPathChecker.cs
@@ -0,0 +1,27 @@
+using System.Collections.Generic;
+using System.IO;
+using System.Linq;
+
+namespace PathCleaner
+{
+    class NoExecutablesPathChecker : IPathChecker
+    {
+        private static HashSet<string> executableExtensions = new HashSet<string>() 
+        { 
+            ".exe", ".com", ".bat", ".cmd", ".ps1", ".dll"
+        };
+
+        public string Reason
+        {
+            get { return "No executables"; }
+        }
+
+        public bool Identify(string folder, string previousFolder)
+        {
+            return !Directory.EnumerateFiles(folder)
+                .Where(s => executableExtensions.Contains(Path.GetExtension(s)))
+                .Any();
+        }
+    }
+
+}
diff --git a/ProblemIdentifier.cs b/ProblemIdentifier.cs
new file mode 100644
index 0000000..d861a43
--- /dev/null
+++ b/ProblemIdentifier.cs
@@ -0,0 +1,42 @@
+using System.Collections.Generic;
+using System.Linq;
+
+namespace PathCleaner
+{
+    class ProblemIdentifier
+    {
+        public IEnumerable<IPathChecker> Checkers { get; private set; }
+        public PathString PathString { get; private set; }
+
+        public ProblemIdentifier(PathString pathString, IEnumerable<IPathChecker> checkers)
+        {
+            this.PathString = pathString;
+            this.Checkers = checkers;
+        }
+
+        public IEnumerable<PathProblem> Problems
+        {
+            get
+            {
+                var sortedFolders = new List<string>(PathString.Folders.OrderBy(s => s));
+                string previousFolder = null;
+                foreach(string folder in sortedFolders)
+                {
+                    var problem = Checkers.Where(c => c.Identify(folder, previousFolder))
+                        .Select(c => new PathProblem
+                        {
+                            Path = folder,
+                            Reason = c.Reason,
+                        })
+                        .FirstOrDefault();
+                    if (problem != null)
+                    {
+                        yield return problem;
+                    }
+                    previousFolder = folder;
+                }
+            }
+        }
+
+    }
+}