diff --git a/src/modules/powerrename/lib/Helpers.cpp b/src/modules/powerrename/lib/Helpers.cpp
index 73991c8e9b..040167d6ef 100644
--- a/src/modules/powerrename/lib/Helpers.cpp
+++ b/src/modules/powerrename/lib/Helpers.cpp
@@ -46,6 +46,11 @@ HRESULT GetTransformedFileName(_Out_ PWSTR result, UINT cchMax, _In_ PCWSTR sour
 {
     std::locale::global(std::locale(""));
     HRESULT hr = E_INVALIDARG;
+
+    auto contractionOrSingleQuotedWordCheck = [](std::wstring stem, size_t i) {
+        return !i || stem[i - 1] != '\'' || (i == 1 || iswpunct(stem[i - 2]) || iswspace(stem[i - 2]));
+    };
+
     if (source && flags)
     {
         if (flags & Uppercase)
@@ -156,7 +161,7 @@ HRESULT GetTransformedFileName(_Out_ PWSTR result, UINT cchMax, _In_ PCWSTR sour
 
                 for (size_t i = 0; i < stemLength; i++)
                 {
-                    if (!i || iswspace(stem[i - 1]) || iswpunct(stem[i - 1]))
+                    if (!i || iswspace(stem[i - 1]) || (iswpunct(stem[i - 1]) && contractionOrSingleQuotedWordCheck(stem, i)))
                     {
                         if (iswspace(stem[i]) || iswpunct(stem[i]))
                         {
@@ -167,7 +172,10 @@ HRESULT GetTransformedFileName(_Out_ PWSTR result, UINT cchMax, _In_ PCWSTR sour
                         {
                             wordLength++;
                         }
-                        if (isFirstWord || i + wordLength == stemLength || std::find(exceptions.begin(), exceptions.end(), stem.substr(i, wordLength)) == exceptions.end())
+
+                        auto subStr = stem.substr(i, wordLength);
+                        std::transform(subStr.begin(), subStr.end(), subStr.begin(), ::towlower);
+                        if (isFirstWord || i + wordLength == stemLength || std::find(exceptions.begin(), exceptions.end(), subStr) == exceptions.end())
                         {
                             stem[i] = towupper(stem[i]);
                             isFirstWord = false;
@@ -205,13 +213,16 @@ HRESULT GetTransformedFileName(_Out_ PWSTR result, UINT cchMax, _In_ PCWSTR sour
 
                 for (size_t i = 0; i < stemLength; i++)
                 {
-                    if (!i || iswspace(stem[i - 1]) || iswpunct(stem[i - 1]))
+                    if (!i || iswspace(stem[i - 1]) || (iswpunct(stem[i - 1]) && contractionOrSingleQuotedWordCheck(stem, i)))
                     {
                         if (iswspace(stem[i]) || iswpunct(stem[i]))
                         {
                             continue;
                         }
-                        stem[i] = towupper(stem[i]);
+                        else
+                        {
+                            stem[i] = towupper(stem[i]);
+                        }
                     }
                     else
                     {
diff --git a/src/modules/powerrename/unittests/PowerRenameManagerTests.cpp b/src/modules/powerrename/unittests/PowerRenameManagerTests.cpp
index c3a57dfc8b..c6145ff0a7 100644
--- a/src/modules/powerrename/unittests/PowerRenameManagerTests.cpp
+++ b/src/modules/powerrename/unittests/PowerRenameManagerTests.cpp
@@ -91,11 +91,15 @@ namespace PowerRenameManagerTests
 
             Assert::IsTrue(replaceSuccess);
 
+            std::vector<std::wstring> shouldRename = { L"not ", L"" };
+
             // Verify the rename occurred
             for (int i = 0; i < numPairs; i++)
             {
-                Assert::IsTrue(testFileHelper.PathExists(renamePairs[i].originalName) == !renamePairs[i].shouldRename);
-                Assert::IsTrue(testFileHelper.PathExists(renamePairs[i].newName) == renamePairs[i].shouldRename);
+                Assert::IsTrue(testFileHelper.PathExistsCaseSensitive(renamePairs[i].originalName) == !renamePairs[i].shouldRename, 
+                               (std::wstring(L"The path: [" +  renamePairs[i].originalName + L"] should ") + shouldRename[!renamePairs[i].shouldRename] + L"exist.").c_str());
+                Assert::IsTrue(testFileHelper.PathExistsCaseSensitive(renamePairs[i].newName) == renamePairs[i].shouldRename,
+                               (std::wstring(L"The path: [" + renamePairs[i].newName + L"] should ") + shouldRename[renamePairs[i].shouldRename] + L"exist.").c_str());
             }
 
             Assert::IsTrue(mgr->Shutdown() == S_OK);
@@ -250,7 +254,19 @@ namespace PowerRenameManagerTests
         TEST_METHOD (VerifyTitlecaseTransform)
         {
             rename_pairs renamePairs[] = {
-                { L"foo and the to", L"Bar and the To", false, true, 0 },
+                { L"foo And The To", L"Bar and the To", false, true, 0 },
+                { L"foo And The To.txt", L"Bar and the To.txt", true, true, 0 },
+                { L"Test", L"Test_norename", false, false, 0 }
+            };
+
+            RenameHelper(renamePairs, ARRAYSIZE(renamePairs), L"foo", L"bar", SYSTEMTIME{ 2020, 7, 3, 22, 15, 6, 42, 453 }, DEFAULT_FLAGS | Titlecase);
+        }      
+
+        TEST_METHOD (VerifyTitlecaseWithApostropheTransform)
+        {
+            rename_pairs renamePairs[] = {
+                { L"the foo i'll and i've you're dogs' the i'd it's i'm don't to y'all", L"The Bar I'll and I've You're Dogs' the I'd It's I'm Don't to Y'all", false, true, 0 },
+                { L"'the 'foo' 'i'll' and i've you're dogs' the 'i'd' it's i'm don't to y'all.txt", L"'The 'Bar' 'I'll' and I've You're Dogs' the 'I'd' It's I'm Don't to Y'all.txt", true, true, 0 },
                 { L"Test", L"Test_norename", false, false, 0 }
             };
 
@@ -267,10 +283,22 @@ namespace PowerRenameManagerTests
             RenameHelper(renamePairs, ARRAYSIZE(renamePairs), L"foo", L"bar", SYSTEMTIME{ 2020, 7, 3, 22, 15, 6, 42, 453 }, DEFAULT_FLAGS | Capitalized);
         }
 
+        TEST_METHOD (VerifyCapitalizedWithApostropheTransform)
+        {
+            rename_pairs renamePairs[] = {
+                { L"foo i'll and i've you're dogs' the i'd it's i'm don't to y'all", L"Bar I'll And I've You're Dogs' The I'd It's I'm Don't To Y'all", false, true, 0 },
+                { L"'foo i'll 'and' i've you're dogs' the i'd it's i'm don't to y'all.txt", L"'Bar I'll 'And' I've You're Dogs' The I'd It's I'm Don't To Y'all.txt", true, true, 0 },
+                { L"Test", L"Test_norename", false, false, 0 }
+            };
+
+            RenameHelper(renamePairs, ARRAYSIZE(renamePairs), L"foo", L"bar", SYSTEMTIME{ 2020, 7, 3, 22, 15, 6, 42, 453 }, DEFAULT_FLAGS | Capitalized);
+        }
+
         TEST_METHOD (VerifyNameOnlyTransform)
         {
             rename_pairs renamePairs[] = {
-                { L"foo.txt", L"BAR.txt", false, true, 0 },
+                { L"foo.foo", L"BAR.foo", true, true, 0 },
+                { L"foo.txt", L"BAR.TXT", false, true, 0 },
                 { L"TEST", L"TEST_norename", false, false, 1 }
             };
 
diff --git a/src/modules/powerrename/unittests/TestFileHelper.cpp b/src/modules/powerrename/unittests/TestFileHelper.cpp
index 6d55ae0659..e7b2a1a3ea 100644
--- a/src/modules/powerrename/unittests/TestFileHelper.cpp
+++ b/src/modules/powerrename/unittests/TestFileHelper.cpp
@@ -47,6 +47,19 @@ bool CTestFileHelper::PathExists(_In_ const std::wstring path)
     return fs::exists(fullPath);
 }
 
+bool CTestFileHelper::PathExistsCaseSensitive(_In_ const std::wstring path)
+{
+    fs::path tempDirPath = fs::path(_tempDirectory);
+    for (const auto& entry : fs::directory_iterator(tempDirPath))
+    {
+        if (entry.path().filename().wstring() == path)
+        {
+            return true;
+        }
+    }
+    return false;
+}
+
 bool CTestFileHelper::_CreateTempDirectory()
 {
     // Initialize to the temp directory
diff --git a/src/modules/powerrename/unittests/TestFileHelper.h b/src/modules/powerrename/unittests/TestFileHelper.h
index 0ccfe1f641..8f6f12c96b 100644
--- a/src/modules/powerrename/unittests/TestFileHelper.h
+++ b/src/modules/powerrename/unittests/TestFileHelper.h
@@ -14,6 +14,7 @@ public:
     bool AddFolder(_In_ const std::wstring path);
     const std::filesystem::path GetTempDirectory() { return _tempDirectory; }
     bool PathExists(_In_ const std::wstring path);
+    bool PathExistsCaseSensitive(_In_ const std::wstring path);
     std::filesystem::path GetFullPath(_In_ const std::wstring path);
 
 private: