diff --git a/3rdparty/python/requirements.txt b/3rdparty/python/requirements.txt
index b73ca081fe4..9c3febd7d06 100644
--- a/3rdparty/python/requirements.txt
+++ b/3rdparty/python/requirements.txt
@@ -15,7 +15,7 @@ humbug==0.2.7
 
 ijson==3.1.4
 packaging==21.3
-pex==2.1.101
+pex==2.1.102
 psutil==5.9.0
 # This should be compatible with pytest.py, although it can be looser so that we don't
 # over-constrain pantsbuild.pants.testutil
diff --git a/3rdparty/python/user_reqs.lock b/3rdparty/python/user_reqs.lock
index 91edfab4318..b09f6f49493 100644
--- a/3rdparty/python/user_reqs.lock
+++ b/3rdparty/python/user_reqs.lock
@@ -20,7 +20,7 @@
 //     "ijson==3.1.4",
 //     "mypy-typing-asserts==0.1.1",
 //     "packaging==21.3",
-//     "pex==2.1.101",
+//     "pex==2.1.102",
 //     "psutil==5.9.0",
 //     "pydevd-pycharm==203.5419.8",
 //     "pytest<7.1.0,>=6.2.4",
@@ -832,13 +832,13 @@
           "artifacts": [
             {
               "algorithm": "sha256",
-              "hash": "fa501a025417bd35d07ece39482502501ba3bc2a94be476db33a5452be0da32f",
-              "url": "https://files.pythonhosted.org/packages/77/11/696975448606b1b29ebc877aae43035537cb1ddc2e6a8f85a2ee448ce2e2/pex-2.1.101-py2.py3-none-any.whl"
+              "hash": "3743864e09e1017224c5dc6476463ed24b6fea3ac62d379fedc2c6182b2f2159",
+              "url": "https://files.pythonhosted.org/packages/ef/41/a242ae32220cd2951faedddfed3db85393906497526060954b064f9022b7/pex-2.1.102-py2.py3-none-any.whl"
             },
             {
               "algorithm": "sha256",
-              "hash": "d966f2ac9fbf32c6941a798fa8035f74546a056168ac3ef35fca72131e60e1a9",
-              "url": "https://files.pythonhosted.org/packages/70/ff/5eaeef82710ed8f43bede93e31f1801357e3f06407c99f9a24d72d35cd60/pex-2.1.101.tar.gz"
+              "hash": "fa34cef083bede3ea45413638c24e84698949904ef0559994e734b6d21de363c",
+              "url": "https://files.pythonhosted.org/packages/71/f1/125bbeb76821dfe20fc78eb6ebaf963c67ee3a32cc37c907ae54f743c69e/pex-2.1.102.tar.gz"
             }
           ],
           "project_name": "pex",
@@ -846,7 +846,7 @@
             "subprocess32>=3.2.7; extra == \"subprocess\" and python_version < \"3\""
           ],
           "requires_python": "!=3.0.*,!=3.1.*,!=3.2.*,!=3.3.*,!=3.4.*,<3.12,>=2.7",
-          "version": "2.1.101"
+          "version": "2.1.102"
         },
         {
           "artifacts": [
@@ -1689,19 +1689,19 @@
           "artifacts": [
             {
               "algorithm": "sha256",
-              "hash": "20588c285e5ca336d908d2705994830a83cfb6bda40fc356bbafaf430a262013",
-              "url": "https://files.pythonhosted.org/packages/04/9f/65ce26fb8b191c91ec7afe3804da305c02331111d8abec7bf706a35b68a5/types_urllib3-1.26.16-py3-none-any.whl"
+              "hash": "0d027fcd27dbb3cb532453b4d977e05bc1e13aefd70519866af211b3003d895d",
+              "url": "https://files.pythonhosted.org/packages/92/6f/37d8bc1572c4e6f1562ed7847f9ce3a48e23bd54ddbaf6786a6adee9f24d/types_urllib3-1.26.17-py3-none-any.whl"
             },
             {
               "algorithm": "sha256",
-              "hash": "8bb3832c684c30cbed40b96e28bc04703becb2b97d82ac65ba4b968783453b0e",
-              "url": "https://files.pythonhosted.org/packages/7f/71/f6078ac156b931e70ab206fc84938697ca1f3a08510a2e08a683ba1b0317/types-urllib3-1.26.16.tar.gz"
+              "hash": "73fd274524c3fc7cd8cd9ceb0cb67ed99b45f9cb2831013e46d50c1451044800",
+              "url": "https://files.pythonhosted.org/packages/ac/2f/79494805b4f9b55b9c09d78c4bef776e6bf59b49463a046cb3851d1dbd60/types-urllib3-1.26.17.tar.gz"
             }
           ],
           "project_name": "types-urllib3",
           "requires_dists": [],
           "requires_python": null,
-          "version": "1.26.16"
+          "version": "1.26.17"
         },
         {
           "artifacts": [
@@ -2251,7 +2251,7 @@
     }
   ],
   "path_mappings": {},
-  "pex_version": "2.1.101",
+  "pex_version": "2.1.102",
   "prefer_older_binary": false,
   "requirements": [
     "PyYAML<7.0,>=6.0",
@@ -2265,7 +2265,7 @@
     "ijson==3.1.4",
     "mypy-typing-asserts==0.1.1",
     "packaging==21.3",
-    "pex==2.1.101",
+    "pex==2.1.102",
     "psutil==5.9.0",
     "pydevd-pycharm==203.5419.8",
     "pytest<7.1.0,>=6.2.4",
diff --git a/src/python/pants/backend/python/subsystems/lambdex.lock b/src/python/pants/backend/python/subsystems/lambdex.lock
index 53369acdb2f..7d2861a03cd 100644
--- a/src/python/pants/backend/python/subsystems/lambdex.lock
+++ b/src/python/pants/backend/python/subsystems/lambdex.lock
@@ -49,13 +49,13 @@
           "artifacts": [
             {
               "algorithm": "sha256",
-              "hash": "fa501a025417bd35d07ece39482502501ba3bc2a94be476db33a5452be0da32f",
-              "url": "https://files.pythonhosted.org/packages/77/11/696975448606b1b29ebc877aae43035537cb1ddc2e6a8f85a2ee448ce2e2/pex-2.1.101-py2.py3-none-any.whl"
+              "hash": "3743864e09e1017224c5dc6476463ed24b6fea3ac62d379fedc2c6182b2f2159",
+              "url": "https://files.pythonhosted.org/packages/ef/41/a242ae32220cd2951faedddfed3db85393906497526060954b064f9022b7/pex-2.1.102-py2.py3-none-any.whl"
             },
             {
               "algorithm": "sha256",
-              "hash": "d966f2ac9fbf32c6941a798fa8035f74546a056168ac3ef35fca72131e60e1a9",
-              "url": "https://files.pythonhosted.org/packages/70/ff/5eaeef82710ed8f43bede93e31f1801357e3f06407c99f9a24d72d35cd60/pex-2.1.101.tar.gz"
+              "hash": "fa34cef083bede3ea45413638c24e84698949904ef0559994e734b6d21de363c",
+              "url": "https://files.pythonhosted.org/packages/71/f1/125bbeb76821dfe20fc78eb6ebaf963c67ee3a32cc37c907ae54f743c69e/pex-2.1.102.tar.gz"
             }
           ],
           "project_name": "pex",
@@ -63,14 +63,14 @@
             "subprocess32>=3.2.7; extra == \"subprocess\" and python_version < \"3\""
           ],
           "requires_python": "!=3.0.*,!=3.1.*,!=3.2.*,!=3.3.*,!=3.4.*,<3.12,>=2.7",
-          "version": "2.1.101"
+          "version": "2.1.102"
         }
       ],
       "platform_tag": null
     }
   ],
   "path_mappings": {},
-  "pex_version": "2.1.101",
+  "pex_version": "2.1.102",
   "prefer_older_binary": false,
   "requirements": [
     "lambdex==0.1.6"
diff --git a/src/python/pants/backend/python/util_rules/pex_cli.py b/src/python/pants/backend/python/util_rules/pex_cli.py
index 81ecb5b6a81..bfb2f6271b2 100644
--- a/src/python/pants/backend/python/util_rules/pex_cli.py
+++ b/src/python/pants/backend/python/util_rules/pex_cli.py
@@ -39,7 +39,7 @@ class PexCli(TemplatedExternalTool):
     name = "pex"
     help = "The PEX (Python EXecutable) tool (https://github.com/pantsbuild/pex)."
 
-    default_version = "v2.1.101"
+    default_version = "v2.1.102"
     default_url_template = "https://github.com/pantsbuild/pex/releases/download/{version}/pex"
     version_constraints = ">=2.1.101,<3.0"
 
@@ -50,8 +50,8 @@ def default_known_versions(cls):
                 (
                     cls.default_version,
                     plat,
-                    "d1e29e060b79307719be2a40d16234d1cadd5fc1abab039e091ce3cba8a47cd9",
-                    "3813284",
+                    "e088ac4608095f49fa232be142e9845fe27d84b86797e52e0d03e1b62488ea5c",
+                    "3814219",
                 )
             )
             for plat in ["macos_arm64", "macos_x86_64", "linux_x86_64", "linux_arm64"]