diff --git a/.gitignore b/.gitignore
index 1e2c77e6..a26083d1 100644
--- a/.gitignore
+++ b/.gitignore
@@ -22,3 +22,4 @@ share/
 .idea/
 .vscode/
 codealike.json
+.python-version
\ No newline at end of file
diff --git a/docs/source/_static/debugging_support.png b/docs/source/_static/debugging_support.png
new file mode 100644
index 00000000..9c12d6a5
Binary files /dev/null and b/docs/source/_static/debugging_support.png differ
diff --git a/docs/source/conf.py b/docs/source/conf.py
index d58ae0e0..35b3dcc7 100644
--- a/docs/source/conf.py
+++ b/docs/source/conf.py
@@ -22,7 +22,7 @@
 author = 'Darren Burns'
 
 # The full version, including alpha/beta/rc tags
-release = '0.51.2b0'
+release = '0.52.0b0'
 
 
 # -- General configuration ---------------------------------------------------
diff --git a/docs/source/guide/running_tests.rst b/docs/source/guide/running_tests.rst
index ed0c6288..eb306081 100644
--- a/docs/source/guide/running_tests.rst
+++ b/docs/source/guide/running_tests.rst
@@ -203,4 +203,13 @@ output.
 .. image:: ../_static/show_diff_symbols.png
     :align: center
     :height: 150
-    :alt: Ward output with diff symbols enabled
\ No newline at end of file
+    :alt: Ward output with diff symbols enabled
+
+Debugging your code with ``pdb``/``breakpoint()``
+-------------------------------------------------
+
+Ward will automatically disable output capturing when you use `pdb.set_trace()` or `breakpoint()`, and re-enable it when you exit the debugger.
+
+.. image:: ../_static/debugging_support.png
+    :align: center
+    :alt: Ward debugging example
diff --git a/pyproject.toml b/pyproject.toml
index 9eb724f0..c666a926 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -7,7 +7,7 @@ path = ["ward/tests"]
 
 [tool.poetry]
 name = "ward"
-version = "0.51.2b0"
+version = "0.52.0b0"
 description = "A modern Python testing framework"
 exclude = ["ward/tests"]
 authors = ["Darren Burns <darrenb900@gmail.com>"]
diff --git a/ward/config.py b/ward/config.py
index d1a0cd2a..ba5fdf14 100644
--- a/ward/config.py
+++ b/ward/config.py
@@ -12,6 +12,14 @@
 CONFIG_FILE = "pyproject.toml"
 
 
+def _breakpoint_supported() -> bool:
+    try:
+        breakpoint
+    except NameError:
+        return False
+    return True
+
+
 def read_config_toml(project_root: Path, config_file: str) -> Config:
     path = project_root / config_file
     if not path.is_file():
diff --git a/ward/debug.py b/ward/debug.py
new file mode 100644
index 00000000..56adfe1e
--- /dev/null
+++ b/ward/debug.py
@@ -0,0 +1,59 @@
+import importlib
+import inspect
+import io
+import os
+import warnings
+
+import click
+import sys
+
+from ward.config import _breakpoint_supported
+from ward.terminal import console
+
+original_stdout = sys.stdout
+
+
+def init_breakpointhooks(pdb_module, sys_module) -> None:
+    # breakpoint() is Python 3.7+
+    if _breakpoint_supported():
+        sys_module.breakpointhook = _breakpointhook
+    pdb_module.set_trace = _breakpointhook
+
+
+def _breakpointhook(*args, **kwargs):
+    hookname = os.getenv("PYTHONBREAKPOINT")
+    if hookname is None or len(hookname) == 0:
+        hookname = "pdb.set_trace"
+        kwargs.setdefault("frame", inspect.currentframe().f_back)
+    elif hookname == "0":
+        return None
+
+    modname, dot, funcname = hookname.rpartition(".")
+    if dot == "":
+        modname = "builtins"
+
+    try:
+        module = importlib.import_module(modname)
+        if hookname == "pdb.set_trace":
+            set_trace = module.Pdb(stdout=original_stdout, skip=["ward*"]).set_trace
+            hook = set_trace
+        else:
+            hook = getattr(module, funcname)
+    except:
+        warnings.warn(
+            f"Ignoring unimportable $PYTHONBREAKPOINT: {hookname}", RuntimeWarning
+        )
+        return None
+
+    context = click.get_current_context()
+    capture_enabled = context.params.get("capture_output")
+    capture_active = isinstance(sys.stdout, io.StringIO)
+
+    if capture_enabled and capture_active:
+        sys.stdout = original_stdout
+        console.print(f"Entering {modname} - output capturing disabled.", style="info")
+        return hook(*args, **kwargs)
+    return hook(*args, **kwargs)
+
+
+__breakpointhook__ = _breakpointhook
diff --git a/ward/run.py b/ward/run.py
index 6fd05675..eb0ed082 100644
--- a/ward/run.py
+++ b/ward/run.py
@@ -1,7 +1,9 @@
+import pdb
+
 import sys
 from pathlib import Path
 from timeit import default_timer
-from typing import Optional, Tuple, Union
+from typing import Optional, Tuple
 
 import click
 import click_completion
@@ -19,6 +21,7 @@
     filter_fixtures,
 )
 from ward.config import set_defaults_from_config
+from ward.debug import init_breakpointhooks
 from ward.rewrite import rewrite_assertions_in_tests
 from ward.suite import Suite
 from ward.fixtures import _DEFINED_FIXTURES
@@ -139,6 +142,7 @@ def test(
     dry_run: bool,
 ):
     """Run tests."""
+    init_breakpointhooks(pdb, sys)
     start_run = default_timer()
     paths = [Path(p) for p in path]
     mod_infos = get_info_for_modules(paths, exclude)
@@ -146,7 +150,6 @@ def test(
     unfiltered_tests = get_tests_in_modules(modules, capture_output)
     filtered_tests = list(filter_tests(unfiltered_tests, query=search, tag_expr=tags,))
 
-    # Rewrite assertions in each test
     tests = rewrite_assertions_in_tests(filtered_tests)
 
     time_to_collect = default_timer() - start_run
diff --git a/ward/terminal.py b/ward/terminal.py
index 08245cc3..6b6b3127 100644
--- a/ward/terminal.py
+++ b/ward/terminal.py
@@ -87,21 +87,6 @@ def make_indent(depth=1):
 console = Console(theme=theme, highlighter=NullHighlighter())
 
 
-def print_no_break(e: Any):
-    console.print(e, end="")
-
-
-def multiline_description(s: str, indent: int, width: int) -> str:
-    wrapped = wrap(s, width)
-    if len(wrapped) == 1:
-        return wrapped[0]
-    rv = wrapped[0]
-    for line in wrapped[1:]:
-        indent_str = " " * indent
-        rv += f"\n{indent_str}{line}"
-    return rv
-
-
 def format_test_id(test_result: TestResult) -> str:
     """
     Format module name, line number, and test case number
diff --git a/ward/testing.py b/ward/testing.py
index dd7ee94a..8a95eb0c 100644
--- a/ward/testing.py
+++ b/ward/testing.py
@@ -4,6 +4,7 @@
 import inspect
 import traceback
 import uuid
+from bdb import BdbQuit
 from collections import defaultdict
 from contextlib import ExitStack, closing, redirect_stderr, redirect_stdout
 from dataclasses import dataclass, field
@@ -156,6 +157,12 @@ def run(self, cache: FixtureCache, dry_run=False) -> "TestResult":
             except FixtureError as e:
                 outcome = TestOutcome.FAIL
                 error: Optional[Exception] = e
+            except BdbQuit:
+                # We don't want to treat the user quitting the debugger
+                # as an exception, so we'll ignore BdbQuit. This will
+                # also prevent a large pdb-internal stack trace flooding
+                # the terminal.
+                pass
             except (Exception, SystemExit) as e:
                 outcome = (
                     TestOutcome.XFAIL
diff --git a/ward/tests/test_debug.py b/ward/tests/test_debug.py
new file mode 100644
index 00000000..e374d8d8
--- /dev/null
+++ b/ward/tests/test_debug.py
@@ -0,0 +1,32 @@
+from types import SimpleNamespace
+from unittest.mock import Mock
+
+from ward import test, debug
+from ward.debug import init_breakpointhooks, _breakpointhook
+
+
+@test("init_breakpointhooks always patches pdb.set_trace")
+def _():
+    mock_pdb = Mock()
+    init_breakpointhooks(pdb_module=mock_pdb, sys_module=Mock())
+    assert mock_pdb.set_trace == _breakpointhook
+
+
+@test("init_breakpointhooks sets sys.breakpointhook when it's supported")
+def _():
+    old_func = debug._breakpoint_supported
+    debug._breakpoint_supported = lambda: True
+    mock_sys = SimpleNamespace()
+    init_breakpointhooks(pdb_module=Mock(), sys_module=mock_sys)
+    debug._breakpoint_supported = old_func
+    assert mock_sys.breakpointhook == _breakpointhook
+
+
+@test("init_breakpointhooks doesnt set breakpointhook when it's unsupported")
+def _():
+    old_func = debug._breakpoint_supported
+    debug._breakpoint_supported = lambda: False
+    mock_sys = SimpleNamespace()
+    init_breakpointhooks(pdb_module=Mock(), sys_module=mock_sys)
+    debug._breakpoint_supported = old_func
+    assert not hasattr(mock_sys, "breakpointhook")
diff --git a/ward/tests/test_util.py b/ward/tests/test_util.py
index 44049e9c..88415456 100644
--- a/ward/tests/test_util.py
+++ b/ward/tests/test_util.py
@@ -1,9 +1,8 @@
 import os
-import sys
 from pathlib import Path
 
 from ward import test, using, fixture
-from ward.testing import each, xfail, skip
+from ward.testing import each
 from ward.tests.utilities import make_project
 from ward.util import (
     truncate,