diff --git a/libmamba/src/core/util_os.cpp b/libmamba/src/core/util_os.cpp
index ccea2658fb..0c361534c5 100644
--- a/libmamba/src/core/util_os.cpp
+++ b/libmamba/src/core/util_os.cpp
@@ -139,19 +139,25 @@ namespace mamba
     {
         // Needs to be set system-wide & can only be run as admin ...
 
-        auto win_ver = util::windows_version();
+        const auto win_ver = util::windows_version();
+        LOG_DEBUG << fmt::format("Windows version : {}", win_ver ? win_ver.value() : win_ver.error().message);
+
+        static constexpr auto error_message_wrong_version = "Not setting long path registry key;"
+            "Windows version must be at least 10 with the fall 2016 \"Anniversary update\" or newer.";
+
         if (!win_ver.has_value())
         {
-            LOG_WARNING << "Not setting long path registry key; Windows version must be at least 10 "
-                           "with the fall 2016 \"Anniversary update\" or newer.";
+            LOG_WARNING << "failed to acquire Windows version - " << error_message_wrong_version;
             return false;
         }
+
+
         auto split_out = util::split(win_ver.value(), ".");
         if (!(split_out.size() >= 3 && std::stoull(split_out[0]) >= 10
               && std::stoull(split_out[2]) >= 14352))
         {
-            LOG_WARNING << "Not setting long path registry key; Windows version must be at least 10 "
-                           "with the fall 2016 \"Anniversary update\" or newer.";
+            LOG_WARNING << "Windows version found:" << win_ver.value() << " - "
+                        << error_message_wrong_version;
             return false;
         }
 
@@ -164,7 +170,8 @@ namespace mamba
         }
         catch (const winreg::RegException& /*e*/)
         {
-            LOG_INFO << "No LongPathsEnabled key detected.";
+            LOG_INFO << "No LongPathsEnabled key detected. (Windows version = " << win_ver.value()
+                     << ")";
             return false;
         }
 
@@ -173,8 +180,9 @@ namespace mamba
             auto out = Console::stream();
             fmt::print(
                 out,
-                "{}",
-                fmt::styled("Windows long-path support already enabled.", palette.ignored)
+                "{} (Windows version = {})",
+                fmt::styled("Windows long-path support already enabled.", palette.ignored),
+                win_ver.value()
             );
             return true;
         }
diff --git a/libmamba/src/util/os_win.cpp b/libmamba/src/util/os_win.cpp
index 2d10fdb06e..5ab0f74597 100644
--- a/libmamba/src/util/os_win.cpp
+++ b/libmamba/src/util/os_win.cpp
@@ -218,7 +218,11 @@ namespace mamba::util
         // from python
         static const auto ver_output_regex = std::regex(R"((?:([\w ]+) ([\w.]+) .*\[.* ([\d.]+)\]))");
 
-        if (auto rmatch = std::smatch(); std::regex_match(out, rmatch, ver_output_regex))
+        // The output of the command could contain multiple unrelated lines, so we need to check
+        // every lines, which is why we need to search in a loop until reaching the end of the output.
+        std::smatch rmatch;
+        auto start_it = out.cbegin();
+        while (std::regex_search(start_it, out.cend(), rmatch, ver_output_regex))
         {
             std::string full_version = rmatch[3];
             auto version_elems = util::split(full_version, ".");