diff --git a/src/rcore.c b/src/rcore.c
index dd60ab731..9aadce1e4 100644
--- a/src/rcore.c
+++ b/src/rcore.c
@@ -2583,19 +2583,27 @@ const char *GetPrevDirectoryPath(const char *dirPath)
 {
     static char prevDirPath[MAX_FILEPATH_LENGTH] = { 0 };
     memset(prevDirPath, 0, MAX_FILEPATH_LENGTH);
-    int dirPathLength = (int)strlen(dirPath);
 
-    if (dirPathLength <= 3) snprintf(prevDirPath, MAX_FILEPATH_LENGTH, "%s", dirPath);
-
-    for (int i = (dirPathLength - 1); (i >= 0) && (dirPathLength > 3); i--)
+    const int lastIndex = (int)strlen(dirPath) - 1;
+    bool isFile = IsPathFile(dirPath);
+    for (int i = lastIndex; i >= 0; i--)
     {
+        // If the character is a path separator.
         if ((dirPath[i] == '\\') || (dirPath[i] == '/'))
         {
-            // Check for root: "C:\" or "/"
-            if (((i == 2) && (dirPath[1] ==':')) || (i == 0)) i++;
+            // If this character is a leading '/' (e.g. the '/' in "/usr") or
+            // part of a drive root (e.g. "C:\"), include it with the result.
+            if ((i == 0) || ((i == 2) && (dirPath[1] == ':'))) i += 1;
+            // If this character is a trailing path separator (e.g. the last
+            // '/' in "/usr/bin/" or the last '\' in "C:\raylib\"), continue.
+            else if (i == lastIndex) continue;
 
-            memcpy(prevDirPath, dirPath, i);
-            break;
+            if (!isFile)
+            {
+                memcpy(prevDirPath, dirPath, i);
+                break;
+            }
+            else isFile = false;
         }
     }