diff --git a/src/PIL/Image.py b/src/PIL/Image.py
index d7d0a1ae7..adb63b07f 100644
--- a/src/PIL/Image.py
+++ b/src/PIL/Image.py
@@ -2385,7 +2385,7 @@ class Image:
         filename = ""
         open_fp = False
         if is_path(fp):
-            filename = os.fspath(fp)
+            filename = os.path.realpath(os.fspath(fp))
             open_fp = True
         elif fp == sys.stdout:
             try:
diff --git a/src/PIL/ImageFont.py b/src/PIL/ImageFont.py
index 7be2fdf04..256c581df 100644
--- a/src/PIL/ImageFont.py
+++ b/src/PIL/ImageFont.py
@@ -230,7 +230,7 @@ class FreeTypeFont:
             )
 
         if is_path(font):
-            font = os.fspath(font)
+            font = os.path.realpath(os.fspath(font))
             if sys.platform == "win32":
                 font_bytes_path = font if isinstance(font, bytes) else font.encode()
                 try: