diff --git a/.github/actions/fetch-vectors/action.yml b/.github/actions/fetch-vectors/action.yml
index 01ee39394d53..2a310fbfdde7 100644
--- a/.github/actions/fetch-vectors/action.yml
+++ b/.github/actions/fetch-vectors/action.yml
@@ -9,8 +9,8 @@ runs:
       with:
         repository: "C2SP/wycheproof"
         path: "wycheproof"
-        # Latest commit on the wycheproof main branch, as of May 13, 2026.
-        ref: "878e5366008753df2064d40c49f8e2f50f9c6af7" # wycheproof-ref
+        # Latest commit on the wycheproof main branch, as of Jun 04, 2026.
+        ref: "359826b1d45ce454236079236a9ceab78195c415" # wycheproof-ref
         persist-credentials: false
 
     - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 4062a5a7258e..78c5d7baf10b 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -40,18 +40,18 @@ jobs:
           - {VERSION: "3.14", NOXSESSION: "tests-ssh", OPENSSL: {TYPE: "openssl", VERSION: "3.6.2"}}
           - {VERSION: "3.14", NOXSESSION: "rust,tests", OPENSSL: {TYPE: "libressl", VERSION: "4.2.1"}}
           - {VERSION: "3.14", NOXSESSION: "rust,tests", OPENSSL: {TYPE: "libressl", VERSION: "4.3.1"}}
-          # Latest commit on the BoringSSL main branch, as of Jun 03, 2026.
-          - {VERSION: "3.14", NOXSESSION: "rust,tests", OPENSSL: {TYPE: "boringssl", VERSION: "6907a11a7cc67fb9cee3362f8afac9096f2b8a12"}}
+          # Latest commit on the BoringSSL main branch, as of Jun 04, 2026.
+          - {VERSION: "3.14", NOXSESSION: "rust,tests", OPENSSL: {TYPE: "boringssl", VERSION: "ef8c8fc898fa55fd9b5108db5b9b622655827c12"}}
           # Latest tag of AWS-LC main branch, as of May 30, 2026.
           - {VERSION: "3.14", NOXSESSION: "rust,tests", OPENSSL: {TYPE: "aws-lc", VERSION: "v5.0.0"}}
-          # Latest commit on the OpenSSL master branch, as of Jun 03, 2026.
-          - {VERSION: "3.14", NOXSESSION: "tests", OPENSSL: {TYPE: "openssl", VERSION: "4dcf6d276dea963e5d3b1d5de4349f301c17f1ba"}}
+          # Latest commit on the OpenSSL master branch, as of Jun 04, 2026.
+          - {VERSION: "3.14", NOXSESSION: "tests", OPENSSL: {TYPE: "openssl", VERSION: "d099e33e5733bb9d3975fc4f3ac4a85b6ed1a4cb"}}
           # Builds with various Rust versions. Includes MSRV and next
           # potential future MSRV.
           # - 1.95: cfg_select
           - {VERSION: "3.14", NOXSESSION: "rust,tests", RUST: "1.83.0"}
           - {VERSION: "3.14", NOXSESSION: "rust,tests", RUST: "1.83.0", OPENSSL: {TYPE: "aws-lc", VERSION: "v5.0.0"}}
-          - {VERSION: "3.14", NOXSESSION: "rust,tests", RUST: "1.83.0", OPENSSL: {TYPE: "boringssl", VERSION: "6907a11a7cc67fb9cee3362f8afac9096f2b8a12"}}
+          - {VERSION: "3.14", NOXSESSION: "rust,tests", RUST: "1.83.0", OPENSSL: {TYPE: "boringssl", VERSION: "ef8c8fc898fa55fd9b5108db5b9b622655827c12"}}
           - {VERSION: "3.14", NOXSESSION: "rust,tests", RUST: "beta"}
           - {VERSION: "3.14", NOXSESSION: "rust,tests", RUST: "nightly"}
           - {VERSION: "3.14", NOXSESSION: "tests-rust-debug"}
@@ -386,8 +386,8 @@ jobs:
             PATH: paramiko
           - DOWNSTREAM: pyopenssl
             REPO: pyca/pyopenssl
-            # Latest commit on the pyopenssl main branch, as of May 05, 2026.
-            REF: 23208870fab95ba33ab897e5b7d66ceb38ce56f7
+            # Latest commit on the pyopenssl main branch, as of Jun 04, 2026.
+            REF: 7079d6d41c726ca921a3282449eac24789272d14
             PATH: pyopenssl
           - DOWNSTREAM: pyopenssl-release
             REPO: pyca/pyopenssl
@@ -421,8 +421,8 @@ jobs:
             PATH: josepy
           - DOWNSTREAM: mitmproxy
             REPO: mitmproxy/mitmproxy
-            # Latest commit on the mitmproxy main branch, as of Jun 02, 2026.
-            REF: 97add89580ca052047ff564e477ad1a4ab7ec03b
+            # Latest commit on the mitmproxy main branch, as of Jun 04, 2026.
+            REF: 61add6ba7b2d2788adf8c325e8d9270e0f226d6b
             PATH: mitmproxy
           - DOWNSTREAM: scapy
             REPO: secdev/scapy
@@ -431,8 +431,8 @@ jobs:
             PATH: scapy
           - DOWNSTREAM: sigstore-python
             REPO: sigstore/sigstore-python
-            # Latest commit on the sigstore-python main branch, as of Jun 03, 2026.
-            REF: 3566ecd0dd195b73917ab4573c9f5e103d77a0cc
+            # Latest commit on the sigstore-python main branch, as of Jun 04, 2026.
+            REF: 4baa76f7b30ec416d4bba66defc325d5c36dfb20
             PATH: sigstore-python
     name: "Downstream tests for ${{ matrix.DOWNSTREAM }}"
     timeout-minutes: 15