diff --git a/aider/coders/base_coder.py b/aider/coders/base_coder.py
index 5ceea559f..4e9adbf3b 100755
--- a/aider/coders/base_coder.py
+++ b/aider/coders/base_coder.py
@@ -532,6 +532,7 @@ class Coder:
 
         edited, edit_error = self.apply_updates()
         if edit_error:
+            self.update_cur_messages(content, set())
             return edit_error
 
         # TODO: this shouldn't use content, should use self.partial_....
@@ -1006,7 +1007,7 @@ class Coder:
     apply_update_errors = 0
 
     def apply_updates(self):
-        max_apply_update_errors = 2
+        max_apply_update_errors = 3
 
         try:
             edited = self.update_files()
diff --git a/aider/coders/editblock_coder.py b/aider/coders/editblock_coder.py
index ee0ffa666..df29c330f 100644
--- a/aider/coders/editblock_coder.py
+++ b/aider/coders/editblock_coder.py
@@ -32,7 +32,17 @@ class EditBlockCoder(Coder):
                 self.io.write_text(full_path, content)
                 edited.add(path)
                 continue
-            self.io.tool_error(f"Failed to apply edit to {path}")
+            raise ValueError(f"""InvalidEditBlock: edit failed!
+
+{path} does not contain the *exact sequence* of ORIGINAL lines you specified.
+Try again.
+DO NOT skip blank lines, comments, docstrings, etc!
+The ORIGINAL block needs to be EXACTLY the same as the lines in {path} with nothing missing!
+
+{path} does not contain these {len(original.splitlines())} exact lines in a row:
+```
+{original}```
+""")
 
         return edited
 
diff --git a/aider/coders/editblock_prompts.py b/aider/coders/editblock_prompts.py
index 5b9d8ce9b..7eb8ab0d0 100644
--- a/aider/coders/editblock_prompts.py
+++ b/aider/coders/editblock_prompts.py
@@ -33,7 +33,7 @@ some/dir/example.py
 
 Every *edit block* must be fenced with {fence[0]}...{fence[1]} with the correct code language.
 Every *edit block* must start with the full path! *NEVER* propose edit blocks for *read-only* files.
-The ORIGINAL section must be an *exact* set of lines from the file:
+The ORIGINAL section must be an *exact set of sequential lines* from the file:
 - NEVER SKIP LINES!
 - Include all original leading spaces and indentation!