diff --git a/bolt/cli/cli.py b/bolt/cli/cli.py
index 3430affa93..a9055677f2 100644
--- a/bolt/cli/cli.py
+++ b/bolt/cli/cli.py
@@ -13,6 +13,7 @@
 from bolt.env.cli import cli as env_cli
 from bolt.packages import packages
 
+from .formatting import BoltContext
 from .packages import EntryPointGroup, InstalledPackagesGroup
 
 
@@ -334,6 +335,8 @@ def get_command(self, ctx, name):
 
 
 class BoltCommandCollection(click.CommandCollection):
+    context_class = BoltContext
+
     def __init__(self, *args, **kwargs):
         sources = []
 
diff --git a/bolt/cli/formatting.py b/bolt/cli/formatting.py
new file mode 100644
index 0000000000..16d39c1d15
--- /dev/null
+++ b/bolt/cli/formatting.py
@@ -0,0 +1,57 @@
+import click
+from click.formatting import iter_rows, measure_table, term_len, wrap_text
+
+
+class BoltHelpFormatter(click.HelpFormatter):
+    def write_heading(self, heading):
+        styled_heading = click.style(heading, underline=True)
+        self.write(f"{'':>{self.current_indent}}{styled_heading}\n")
+
+    def write_dl(
+        self,
+        rows,
+        col_max=30,
+        col_spacing=2,
+    ):
+        """Writes a definition list into the buffer.  This is how options
+        and commands are usually formatted.
+
+        :param rows: a list of two item tuples for the terms and values.
+        :param col_max: the maximum width of the first column.
+        :param col_spacing: the number of spaces between the first and
+                            second column.
+        """
+        rows = list(rows)
+        widths = measure_table(rows)
+        if len(widths) != 2:
+            raise TypeError("Expected two columns for definition list")
+
+        first_col = min(widths[0], col_max) + col_spacing
+
+        for first, second in iter_rows(rows, len(widths)):
+            first_styled = click.style(first, bold=True)
+            self.write(f"{'':>{self.current_indent}}{first_styled}")
+            if not second:
+                self.write("\n")
+                continue
+            if term_len(first) <= first_col - col_spacing:
+                self.write(" " * (first_col - term_len(first)))
+            else:
+                self.write("\n")
+                self.write(" " * (first_col + self.current_indent))
+
+            text_width = max(self.width - first_col - 2, 10)
+            wrapped_text = wrap_text(second, text_width, preserve_paragraphs=True)
+            lines = wrapped_text.splitlines()
+
+            if lines:
+                self.write(f"{lines[0]}\n")
+
+                for line in lines[1:]:
+                    self.write(f"{'':>{first_col + self.current_indent}}{line}\n")
+            else:
+                self.write("\n")
+
+
+class BoltContext(click.Context):
+    formatter_class = BoltHelpFormatter