diff --git a/dotbot/plugins/link.py b/dotbot/plugins/link.py
index 4a9cc53..7f9ba9f 100644
--- a/dotbot/plugins/link.py
+++ b/dotbot/plugins/link.py
@@ -1,6 +1,8 @@
 import os
 import glob
 import shutil
+from pathlib import Path
+
 import dotbot
 import dotbot.util
 import subprocess
@@ -253,8 +255,9 @@ class Link(dotbot.Plugin):
     def _link(self, dotfile_source, target_path_to_link_at, relative_path, canonical_path, ignore_missing):
         '''
         Links link_name to source.
-        :param target_path_to_link_at is the file path where we are putting a symlink back to
-        dotfile_source
+        :param target_path_to_link_at is the file path where we are putting a symlink
+            (where the file originally lived)
+        :param dotfile_source - source file in dotfiles directory, which file should symlink to
 
         Returns true if successfully linked files.
         '''
@@ -276,29 +279,39 @@ class Link(dotbot.Plugin):
 
         target_path_exists: bool = self._exists(target_path_to_link_at)
         target_file_is_link: bool = self._is_link(target_path_to_link_at)
+
         # get the file/ folder the symlink (located at the target path) is pointed to
         symlink_dest_at_target_path: str = self._get_link_destination(target_path_to_link_at)
 
+        # Expanded, os style paths for reporting/ error checking
+        symlink_loc_clean = os.path.normpath(os.path.expanduser(target_path_to_link_at))
+        dotfile_source_expanded = os.path.expanduser(dotfile_source)
+
         # Check case of links are present but incorrect
         if target_file_is_link and (symlink_dest_at_target_path != dotfile_source):
+            symlink_dest_clean = os.path.abspath(symlink_dest_at_target_path)
             if target_path_exists:
-                self._log.warning("Incorrect link (link exists but target is incorrect) %s -> %s"
-                                  % (target_path_to_link_at, symlink_dest_at_target_path))
+                self._log.warning("Incorrect link (link exists but target is incorrect):\n\t "
+                                  f"{symlink_loc_clean} -> {symlink_dest_clean},\n\t"
+                                  f"Expected {symlink_dest_clean}, found "
+                                  f"{dotfile_source_expanded}"
+                                 )
                 print("Link found:", symlink_dest_at_target_path, "expected", dotfile_source)
             else:
                 # Symlink is broken or dangling
-                self._log.warning("Symlink Invalid %s -> %s" % (target_path_to_link_at, symlink_dest_at_target_path))
+                self._log.warning(f"Symlink Invalid:\n\t {symlink_loc_clean}"
+                                  f"\n\t -> {symlink_dest_clean}")
             return success_flag
 
         if target_path_exists:  # file/ folder we want to put symlink in already exists
             if target_file_is_link:  # already checked if link pointed to wrong location,
                 # so if it's a link we know it's correct
-                self._log.lowinfo("Link exists %s -> %s" % (target_path_to_link_at, dotfile_source))
+                self._log.lowinfo("Link exists %s -> %s" % (symlink_loc_clean, dotfile_source_expanded))
                 success_flag = True
                 return success_flag
             else:  # Not a link
                 self._log.warning(
-                    "%s already exists but is a regular file or directory" % target_path_to_link_at)
+                    "%s already exists but is a regular file or directory" % symlink_loc_clean)
                 return success_flag
         else:
             # target path doesn't exist already, so we try to create the symlink
@@ -307,7 +320,8 @@ class Link(dotbot.Plugin):
                 os.symlink(dotfile_source, destination)
             except OSError as e:
                 msg = textwrap.fill(
-                    f"Linking failed {target_path_to_link_at} -> {dotfile_source}\n ({e})", width=80, subsequent_indent="    ")
+                    f"Linking failed {symlink_loc_clean} -> {dotfile_source_expanded}\n ({e})",
+                    width=80, subsequent_indent="    ")
 
                 self._log.warning(msg)
             except Exception as e:
@@ -316,7 +330,7 @@ class Link(dotbot.Plugin):
                 )
                 raise e
             else:
-                self._log.lowinfo("Creating link %s -> %s" % (target_path_to_link_at, dotfile_source))
+                self._log.lowinfo("Creating link %s -> %s" % (symlink_loc_clean, dotfile_source_expanded))
                 success_flag = True
 
             return success_flag