diff --git a/third_party/python/BUILD b/third_party/python/BUILD
index e5c8b1c..895845d 100644
--- a/third_party/python/BUILD
+++ b/third_party/python/BUILD
@@ -417,9 +417,24 @@ pip_library(
 
 python_wheel(
     name = "debugpy",
-    hashes = ["f058c204341fd7ff800ee0edafc106ca0fb1c9857e8a8895a6e04cca3ddcb7bf"],
+    hashes = [
+        "c1178ae571aff42e61801a38b007af504ec8e05fde1c5c12e5a7efef21009642",  # linux_amd64, Python 3.10
+        "7de0b7dfeedc504421032afba845ae2a7bcc32ddfb07dae2c3ca5442f821c344",  # linux_amd64, Python 3.11
+        "88f47850a4284b88bd2bfee1f26132147d5d504e4e86c22485dfa44b97e19b4b",  # linux_amd64, Python 3.12
+        "84562982dd7cf5ebebfdea667ca20a064e096099997b175fe204e86817f64eaf",  # linux_amd64, Python 3.13
+        "077a7447589ee9bc1ff0cdf443566d0ecf540ac8aa7333b775ebcb8ce9f4ecad",  # linux_amd64, Python 3.14
+        "157e96ffb7f80b3ad36d808646198c90acb46fdcfd8bb1999838f0b6f2b59c64",  # darwin_amd64, Python 3.10
+        "eada6042ad88fa1571b74bd5402ee8b86eded7a8f7b827849761700aff171f1b",  # darwin_amd64/darwin_arm64, Python 3.11
+        "4ae3135e2089905a916909ef31922b2d733d756f66d87345b3e5e52b7a55f13d",  # darwin_amd64/darwin_arm64, Python 3.12
+        "5dff4bb27027821fdfcc9e8f87309a28988231165147c31730128b1c983e282a",  # darwin_amd64/darwin_arm64, Python 3.13
+        "9c74df62fc064cd5e5eaca1353a3ef5a5d50da5eb8058fcef63106f7bebe6173",  # darwin_amd64/darwin_arm64, Python 3.14
+        "5be9bed9ae3be00665a06acaa48f8329d2b9632f15fd09f6a9a8c8d9907e54d7",  # any
+    ],
     licences = ["MIT"],
-    version = "1.5.0",
+    version = "1.8.20",
+    zip_safe = False,
+    # There doesn't seem to be a predictable URL for this version of debugpy so we need to resolve it instead.
+    tool = "//tools:wheel_resolver",
 )
 
 python_wheel(
diff --git a/tools/BUILD b/tools/BUILD
index db64b73..5763c65 100644
--- a/tools/BUILD
+++ b/tools/BUILD
@@ -13,3 +13,20 @@ remote_file(
     binary = True,
     visibility = ["PUBLIC"],
 )
+
+_WHEEL_RESOLVER_VERSION = "2.0.0"
+
+remote_file(
+    name = "wheel_resolver",
+    url =
+    f"https://github.com/please-build/python-rules/releases/download/wheel_resolver-v{_WHEEL_RESOLVER_VERSION}/wheel_resolver-{_WHEEL_RESOLVER_VERSION}-{CONFIG.OS}_{CONFIG.ARCH}",
+    hashes = [
+        "b48315ec1c6670faf7feb2a532a4d0cb104a03113525ef1799062d7576f66b36",  # darwin_amd64
+        "70db6d2eb18ab915f555824a8f29fe0909bcf87db0b583a5d6ad3156a54a034a",  # darwin_arm64
+        "d47802282b4acf1669a1d69531c69eb2dd3f0f069fd8e59d0c9aff946f7aff44",  # freebsd_amd64
+        "6aa0304bde5ab5f68d3415fd8761f6684f5c88835791b0dbd12f909120d797c6",  # linux_amd64
+        "09e340203aa88d4e9de7f61b044d1f29fb688abf3c8b7547f80ad6ca3e441495",  # linux_arm64
+    ],
+    binary = True,
+    visibility = ["PUBLIC"],
+)
diff --git a/tools/please_pex/BUILD b/tools/please_pex/BUILD
index 1483108..02c3642 100644
--- a/tools/please_pex/BUILD
+++ b/tools/please_pex/BUILD
@@ -44,6 +44,7 @@ genrule(
     visibility = ["PUBLIC"],
     deps = [
         "//third_party/python:behave_bootstrap",
+        "//third_party/python:debugpy",
         "//third_party/python:pytest_bootstrap",
         "//third_party/python:unittest_bootstrap",
     ],
diff --git a/tools/please_pex/pex/pex_main.py b/tools/please_pex/pex/pex_main.py
index 374d5c3..76a8fc2 100644
--- a/tools/please_pex/pex/pex_main.py
+++ b/tools/please_pex/pex/pex_main.py
@@ -92,6 +92,7 @@ def _explode_zip():
                 # that the cache has already been prepared.
                 lockfile.write("pex unzip completed")
         sys.path = [PEX_PATH] + [x for x in sys.path if x != PEX]
+        sys.path.insert(1, os.path.join(sys.path[0], '.bootstrap'))
         try:
             yield
         finally: