diff --git a/requirements.txt b/requirements.txt
index 3d7f34802d..184d5b50a5 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -204,30 +204,34 @@ contextlib2==21.6.0 \
     --hash=sha256:3fbdb64466afd23abaf6c977627b75b6139a5a3e8ce38405c5b413aed7a0471f \
     --hash=sha256:ab1e2bfe1d01d968e1b7e8d9023bc51ef3509bba217bb730cee3827e1ee82869
     # via -r requirements.in
-cryptography==41.0.6 \
-    --hash=sha256:068bc551698c234742c40049e46840843f3d98ad7ce265fd2bd4ec0d11306596 \
-    --hash=sha256:0f27acb55a4e77b9be8d550d762b0513ef3fc658cd3eb15110ebbcbd626db12c \
-    --hash=sha256:2132d5865eea673fe6712c2ed5fb4fa49dba10768bb4cc798345748380ee3660 \
-    --hash=sha256:3288acccef021e3c3c10d58933f44e8602cf04dba96d9796d70d537bb2f4bbc4 \
-    --hash=sha256:35f3f288e83c3f6f10752467c48919a7a94b7d88cc00b0668372a0d2ad4f8ead \
-    --hash=sha256:398ae1fc711b5eb78e977daa3cbf47cec20f2c08c5da129b7a296055fbb22aed \
-    --hash=sha256:422e3e31d63743855e43e5a6fcc8b4acab860f560f9321b0ee6269cc7ed70cc3 \
-    --hash=sha256:48783b7e2bef51224020efb61b42704207dde583d7e371ef8fc2a5fb6c0aabc7 \
-    --hash=sha256:4d03186af98b1c01a4eda396b137f29e4e3fb0173e30f885e27acec8823c1b09 \
-    --hash=sha256:5daeb18e7886a358064a68dbcaf441c036cbdb7da52ae744e7b9207b04d3908c \
-    --hash=sha256:60e746b11b937911dc70d164060d28d273e31853bb359e2b2033c9e93e6f3c43 \
-    --hash=sha256:742ae5e9a2310e9dade7932f9576606836ed174da3c7d26bc3d3ab4bd49b9f65 \
-    --hash=sha256:7e00fb556bda398b99b0da289ce7053639d33b572847181d6483ad89835115f6 \
-    --hash=sha256:85abd057699b98fce40b41737afb234fef05c67e116f6f3650782c10862c43da \
-    --hash=sha256:8efb2af8d4ba9dbc9c9dd8f04d19a7abb5b49eab1f3694e7b5a16a5fc2856f5c \
-    --hash=sha256:ae236bb8760c1e55b7a39b6d4d32d2279bc6c7c8500b7d5a13b6fb9fc97be35b \
-    --hash=sha256:afda76d84b053923c27ede5edc1ed7d53e3c9f475ebaf63c68e69f1403c405a8 \
-    --hash=sha256:b27a7fd4229abef715e064269d98a7e2909ebf92eb6912a9603c7e14c181928c \
-    --hash=sha256:b648fe2a45e426aaee684ddca2632f62ec4613ef362f4d681a9a6283d10e079d \
-    --hash=sha256:c5a550dc7a3b50b116323e3d376241829fd326ac47bc195e04eb33a8170902a9 \
-    --hash=sha256:da46e2b5df770070412c46f87bac0849b8d685c5f2679771de277a422c7d0b86 \
-    --hash=sha256:f39812f70fc5c71a15aa3c97b2bbe213c3f2a460b79bd21c40d033bb34a9bf36 \
-    --hash=sha256:ff369dd19e8fe0528b02e8df9f2aeb2479f89b1270d90f96a63500afe9af5cae
+cryptography==43.0.1 \
+    --hash=sha256:014f58110f53237ace6a408b5beb6c427b64e084eb451ef25a28308270086494 \
+    --hash=sha256:1bbcce1a551e262dfbafb6e6252f1ae36a248e615ca44ba302df077a846a8806 \
+    --hash=sha256:203e92a75716d8cfb491dc47c79e17d0d9207ccffcbcb35f598fbe463ae3444d \
+    --hash=sha256:27e613d7077ac613e399270253259d9d53872aaf657471473ebfc9a52935c062 \
+    --hash=sha256:2bd51274dcd59f09dd952afb696bf9c61a7a49dfc764c04dd33ef7a6b502a1e2 \
+    --hash=sha256:38926c50cff6f533f8a2dae3d7f19541432610d114a70808f0926d5aaa7121e4 \
+    --hash=sha256:511f4273808ab590912a93ddb4e3914dfd8a388fed883361b02dea3791f292e1 \
+    --hash=sha256:58d4e9129985185a06d849aa6df265bdd5a74ca6e1b736a77959b498e0505b85 \
+    --hash=sha256:5b43d1ea6b378b54a1dc99dd8a2b5be47658fe9a7ce0a58ff0b55f4b43ef2b84 \
+    --hash=sha256:61ec41068b7b74268fa86e3e9e12b9f0c21fcf65434571dbb13d954bceb08042 \
+    --hash=sha256:666ae11966643886c2987b3b721899d250855718d6d9ce41b521252a17985f4d \
+    --hash=sha256:68aaecc4178e90719e95298515979814bda0cbada1256a4485414860bd7ab962 \
+    --hash=sha256:7c05650fe8023c5ed0d46793d4b7d7e6cd9c04e68eabe5b0aeea836e37bdcec2 \
+    --hash=sha256:80eda8b3e173f0f247f711eef62be51b599b5d425c429b5d4ca6a05e9e856baa \
+    --hash=sha256:8385d98f6a3bf8bb2d65a73e17ed87a3ba84f6991c155691c51112075f9ffc5d \
+    --hash=sha256:88cce104c36870d70c49c7c8fd22885875d950d9ee6ab54df2745f83ba0dc365 \
+    --hash=sha256:9d3cdb25fa98afdd3d0892d132b8d7139e2c087da1712041f6b762e4f807cc96 \
+    --hash=sha256:a575913fb06e05e6b4b814d7f7468c2c660e8bb16d8d5a1faf9b33ccc569dd47 \
+    --hash=sha256:ac119bb76b9faa00f48128b7f5679e1d8d437365c5d26f1c2c3f0da4ce1b553d \
+    --hash=sha256:c1332724be35d23a854994ff0b66530119500b6053d0bd3363265f7e5e77288d \
+    --hash=sha256:d03a475165f3134f773d1388aeb19c2d25ba88b6a9733c5c590b9ff7bbfa2e0c \
+    --hash=sha256:d75601ad10b059ec832e78823b348bfa1a59f6b8d545db3a24fd44362a1564cb \
+    --hash=sha256:de41fd81a41e53267cb020bb3a7212861da53a7d39f863585d13ea11049cf277 \
+    --hash=sha256:e710bf40870f4db63c3d7d929aa9e09e4e7ee219e703f949ec4073b4294f6172 \
+    --hash=sha256:ea25acb556320250756e53f9e20a4177515f012c9eaea17eb7587a8c4d8ae034 \
+    --hash=sha256:f98bf604c82c416bc829e490c700ca1553eafdf2912a91e23a79d97d9801372a \
+    --hash=sha256:fba1007b3ef89946dbbb515aeeb41e30203b004f0b4b00e5e16078b518563289
     # via
     #   josepy
     #   mozilla-django-oidc
@@ -980,9 +984,9 @@ pymemcache==4.0.0 \
     --hash=sha256:27bf9bd1bbc1e20f83633208620d56de50f14185055e49504f4f5e94e94aff94 \
     --hash=sha256:f507bc20e0dc8d562f8df9d872107a278df049fa496805c1431b926f3ddd0eab
     # via -r requirements.in
-pyopenssl==23.3.0 \
-    --hash=sha256:6756834481d9ed5470f4a9393455154bc92fe7a64b7bc6ee2c804e78c52099b2 \
-    --hash=sha256:6b2cba5cc46e822750ec3e5a81ee12819850b11303630d575e98108a079c2b12
+pyopenssl==24.2.1 \
+    --hash=sha256:4247f0dbe3748d560dcbb2ff3ea01af0f9a1a001ef5f7c4c647956ed8cbf0e95 \
+    --hash=sha256:967d5719b12b243588573f39b0c677637145c7a1ffedcd495a487e58177fbb8d
     # via josepy
 pyparsing==3.1.1 \
     --hash=sha256:32c7c0b711493c72ff18a981d24f28aaf9c1fb7ed5e9667c9e84e3db623bdbfb \
diff --git a/webapp/pytest.ini b/webapp/pytest.ini
index 7197e10874..bf68b6169f 100644
--- a/webapp/pytest.ini
+++ b/webapp/pytest.ini
@@ -18,3 +18,5 @@ filterwarnings =
     # pubsub deprecated the return_immediately flag because it negatively impacts performance, but
     # that performance cost is fine for our use case, especially in tests.
     ignore:The return_immediately flag is deprecated and should be set to False.:DeprecationWarning:google.pubsub_v1
+    # josepy 1.14.0 uses a deprecated api, being addressed in https://github.com/certbot/josepy/pull/182
+    ignore:CSR support in pyOpenSSL is deprecated. You should use the APIs in cryptography.:DeprecationWarning:josepy