diff --git a/midas/checker/frames/frame_groupby_methods.py b/midas/checker/frames/frame_groupby_methods.py
index cabf88a..a2efba6 100644
--- a/midas/checker/frames/frame_groupby_methods.py
+++ b/midas/checker/frames/frame_groupby_methods.py
@@ -51,24 +51,25 @@ class FrameGroupByMethodRegistry(MethodRegistry[Call]):
         new_columns: list[DataFrameType.Column] = []
 
         for column in call.groupby.frame.columns:
-            column_groupby: ColumnGroupBy = ColumnGroupBy(column=column.type)
-            result_type: Type = self.typer.call_method(
-                location=call.location,
-                call_expr=call.call_expr,
-                obj=(call.groupby_expr, column_groupby),
-                method_name=method,
-                positional=call.positional,
-                keywords=call.keywords,
-            )
-            if not isinstance(result_type, ColumnType):
-                result_type = ColumnType(type=UnknownType())
-            new_columns.append(
-                DataFrameType.Column(
-                    index=column.index,
-                    name=column.name,
-                    type=result_type,
+            with self.reporter.with_context(f"in column '{column.name}'"):
+                column_groupby: ColumnGroupBy = ColumnGroupBy(column=column.type)
+                result_type: Type = self.typer.call_method(
+                    location=call.location,
+                    call_expr=call.call_expr,
+                    obj=(call.groupby_expr, column_groupby),
+                    method_name=method,
+                    positional=call.positional,
+                    keywords=call.keywords,
+                )
+                if not isinstance(result_type, ColumnType):
+                    result_type = ColumnType(type=UnknownType())
+                new_columns.append(
+                    DataFrameType.Column(
+                        index=column.index,
+                        name=column.name,
+                        type=result_type,
+                    )
                 )
-            )
 
         return DataFrameType(columns=new_columns)
 
diff --git a/midas/checker/frames/frame_methods.py b/midas/checker/frames/frame_methods.py
index 99910e1..dfe0698 100644
--- a/midas/checker/frames/frame_methods.py
+++ b/midas/checker/frames/frame_methods.py
@@ -159,7 +159,10 @@ class FrameMethodRegistry(MethodRegistry[Call]):
                 col_type2 = ColumnType(type=operand[1])
 
             if col_type2 is not None:
-                col_type = self._get_method_result(call, col_type1, col_type2, method)
+                with self.reporter.with_context(f"in column '{column.name}'"):
+                    col_type = self._get_method_result(
+                        call, col_type1, col_type2, method
+                    )
 
             new_column = DataFrameType.Column(
                 index=column.index,
diff --git a/midas/checker/reporter.py b/midas/checker/reporter.py
index 970ef34..8604dcd 100644
--- a/midas/checker/reporter.py
+++ b/midas/checker/reporter.py
@@ -1,5 +1,6 @@
 from __future__ import annotations
 
+from contextlib import contextmanager
 from typing import Optional
 
 from midas.ast.location import Location
@@ -54,6 +55,7 @@ class FileReporter:
     def __init__(self, base_reporter: Reporter, path: Optional[str]) -> None:
         self.base_reporter: Reporter = base_reporter
         self.path: Optional[str] = path
+        self._context: list[str] = []
 
     def for_file(self, path: Optional[str]) -> FileReporter:
         """Create a new file reporter for the given path with the same base reporter
@@ -66,6 +68,14 @@ class FileReporter:
         """
         return FileReporter(self.base_reporter, path)
 
+    @contextmanager
+    def with_context(self, ctx: str):
+        self._context.append(ctx)
+        try:
+            yield
+        finally:
+            self._context.pop()
+
     def report(self, type: DiagnosticType, location: Location, message: str):
         """Report a diagnostic to the base reporter
 
@@ -74,6 +84,8 @@ class FileReporter:
             location (Location): the location of the diagnostic in the file
             message (str): the diagnostic's message
         """
+        for ctx in self._context:
+            message = message + ", " + ctx
         self.base_reporter.report(self.path, type, location, message)
 
     def error(self, location: Location, message: str):