diff --git a/src/Archiver.cpp b/src/Archiver.cpp
index df32a25..ff74a93 100644
--- a/src/Archiver.cpp
+++ b/src/Archiver.cpp
@@ -40,24 +40,31 @@ fs::path archive_extension(const fs::path& path) {
 fs::path strip_archive_extension(const fs::path& path) {
   // TODO: creates lots of paths, refactor
   int longest_ext = 0;
+  int tmp_longest_ext = 0;
   fs::path tmp_ext;
   fs::path tmp_path = path;
   fs::path stem_path = path;
 
+  spdlog::debug("Checking {} extensions", path);
+
   while (tmp_path.has_extension()) {
     tmp_ext = tmp_path.extension() += tmp_ext;
-    auto search = extensions_format.find(tmp_ext);
+    spdlog::debug("Looking for {} in known extensions", tmp_ext);
 
+    auto search = extensions_format.find(tmp_ext);
+    tmp_longest_ext++;
     if (search != extensions_format.end()) {
       // (Combined) extension known. Remember as `longest_ext` and keep
       // looking for even longer extensions.
-      longest_ext++;
+      longest_ext = tmp_longest_ext;
     }  // else: (Combined) extension not known, keep `longest_ext` as-is but try longer
        // extensions
 
+    spdlog::debug("Stemming {} to {}", tmp_path, tmp_path.stem());
     tmp_path = tmp_path.stem();
   }
 
+  spdlog::debug("Found {} extensions", longest_ext);
   tmp_path = path;
   for(int i=0; i<longest_ext; i++) tmp_path = tmp_path.stem();
 
diff --git a/src/Xwim.cpp b/src/Xwim.cpp
index d6d7ef4..223fedd 100644
--- a/src/Xwim.cpp
+++ b/src/Xwim.cpp
@@ -2,10 +2,12 @@
 
 #include <spdlog/spdlog.h>
 
+#include <algorithm>
 #include <cstdlib>
 #include <filesystem>
 #include <ios>
 #include <iostream>
+#include <iterator>
 #include <random>
 #include <string>
 
@@ -45,12 +47,42 @@ void Xwim::dwim() {
       break;
     case Action::EXTRACT:
       this->archiver->extract(*ins.begin(), out);
+      sanitize_output();
       break;
     default:
       spdlog::error("Unknown action");
   }
 }
 
+void Xwim::sanitize_output() {
+  fs::path in_stripped = xwim::strip_archive_extension(*ins.begin());
+
+  int count = 0;
+  fs::directory_entry first_entry;
+  for(auto& e: fs::directory_iterator(out)) {
+    count++;
+    if(first_entry.path().empty()) {
+      first_entry = e;
+    }
+  }
+
+  if (count >= 2) {
+    spdlog::debug("Found multiple entries in extraction directory. Moving {} to {}", out, in_stripped);
+    fs::rename(out, in_stripped);
+  } else {
+    if(first_entry.is_directory()) {
+      spdlog::debug("Found single directory in extraction directory. Moving {} to {}",
+          first_entry.path(), in_stripped);
+      fs::rename(first_entry, in_stripped);
+      fs::remove(out);
+    } else {
+      spdlog::debug(
+          "Found single file in extraction directory. Moving {} to {}", out, in_stripped);
+      fs::rename(out, in_stripped);
+    }
+  }
+}
+
 void Xwim::infer_action() {
   if (action != Action::UNKNOWN) return;
 
@@ -131,4 +163,4 @@ void Xwim::setIns(vector<fs::path> ins) {
                  (ins.size() - this->ins.size()));
   }
 }
-}
+}  // namespace xwim
diff --git a/src/Xwim.hpp b/src/Xwim.hpp
index b91f669..6741bb7 100644
--- a/src/Xwim.hpp
+++ b/src/Xwim.hpp
@@ -28,6 +28,7 @@ class Xwim {
   void infer_output();
   void infer_compression_output();
   void infer_extraction_output();
+  void sanitize_output();
 
  public:
   Xwim();