diff --git a/Cargo.lock b/Cargo.lock
index c3e83c9b56..b9d790ee03 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -1495,8 +1495,8 @@ dependencies = [
  "rustls",
  "rustls-native-certs",
  "rustls-pemfile",
+ "rustls-webpki",
  "serde",
- "webpki",
  "webpki-roots",
 ]
 
@@ -2752,7 +2752,7 @@ dependencies = [
  "socket2",
  "widestring",
  "winapi",
- "winreg",
+ "winreg 0.10.1",
 ]
 
 [[package]]
@@ -3980,9 +3980,9 @@ checksum = "4bf2521270932c3c7bed1a59151222bd7643c79310f2916f01925e1e16255698"
 
 [[package]]
 name = "reqwest"
-version = "0.11.18"
+version = "0.11.20"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "cde824a14b7c14f85caff81225f411faacc04a2013f41670f41443742b1c1c55"
+checksum = "3e9ad3fe7488d7e34558a2033d45a0c90b72d97b4f80705666fea71472e2e6a1"
 dependencies = [
  "async-compression",
  "base64 0.21.0",
@@ -4018,7 +4018,7 @@ dependencies = [
  "wasm-streams",
  "web-sys",
  "webpki-roots",
- "winreg",
+ "winreg 0.50.0",
 ]
 
 [[package]]
@@ -4160,9 +4160,9 @@ dependencies = [
 
 [[package]]
 name = "rustls"
-version = "0.21.0"
+version = "0.21.6"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "07180898a28ed6a7f7ba2311594308f595e3dd2e3c3812fa0a80a47b45f17e5d"
+checksum = "1d1feddffcfcc0b33f5c6ce9a29e341e4cd59c3f78e7ee45f4a40c038b1d6cbb"
 dependencies = [
  "log",
  "ring",
@@ -4172,9 +4172,9 @@ dependencies = [
 
 [[package]]
 name = "rustls-native-certs"
-version = "0.6.2"
+version = "0.6.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "0167bac7a9f490495f3c33013e7722b53cb087ecbe082fb0c6387c96f634ea50"
+checksum = "a9aace74cb666635c918e9c12bc0d348266037aa8eb599b5cba565709a8dff00"
 dependencies = [
  "openssl-probe",
  "rustls-pemfile",
@@ -4193,9 +4193,9 @@ dependencies = [
 
 [[package]]
 name = "rustls-webpki"
-version = "0.100.2"
+version = "0.101.4"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e98ff011474fa39949b7e5c0428f9b4937eda7da7848bbb947786b7be0b27dab"
+checksum = "7d93931baf2d282fff8d3a532bbfd7653f734643161b87e3e01e59a04439bf0d"
 dependencies = [
  "ring",
  "untrusted",
@@ -4266,11 +4266,11 @@ dependencies = [
 
 [[package]]
 name = "schannel"
-version = "0.1.21"
+version = "0.1.22"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "713cfb06c7059f3588fb8044c0fad1d09e3c01d225e25b9220dbfdcf16dbb1b3"
+checksum = "0c3733bf4cf7ea0880754e19cb5a462007c4a8c1914bff372ccc95b464f1df88"
 dependencies = [
- "windows-sys 0.42.0",
+ "windows-sys 0.48.0",
 ]
 
 [[package]]
@@ -4356,9 +4356,9 @@ dependencies = [
 
 [[package]]
 name = "security-framework"
-version = "2.8.2"
+version = "2.9.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "a332be01508d814fed64bf28f798a146d73792121129962fdf335bb3c49a4254"
+checksum = "05b64fb303737d99b81884b2c63433e9ae28abebe5eb5045dcdd175dc2ecf4de"
 dependencies = [
  "bitflags 1.3.2",
  "core-foundation",
@@ -4369,9 +4369,9 @@ dependencies = [
 
 [[package]]
 name = "security-framework-sys"
-version = "2.8.0"
+version = "2.9.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "31c9bb296072e961fcbd8853511dd39c2d8be2deb1e17c6860b1d30732b323b4"
+checksum = "e932934257d3b408ed8f30db49d85ea163bfe74961f017f405b025af298f0c7a"
 dependencies = [
  "core-foundation-sys",
  "libc",
@@ -6056,9 +6056,9 @@ checksum = "0046fef7e28c3804e5e38bfa31ea2a0f73905319b677e57ebe37e49358989b5d"
 
 [[package]]
 name = "wasm-streams"
-version = "0.2.3"
+version = "0.3.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "6bbae3363c08332cadccd13b67db371814cd214c2524020932f0804b8cf7c078"
+checksum = "b4609d447824375f43e1ffbc051b50ad8f4b3ae8219680c94452ea05eb240ac7"
 dependencies = [
  "futures-util",
  "js-sys",
@@ -6077,24 +6077,11 @@ dependencies = [
  "wasm-bindgen",
 ]
 
-[[package]]
-name = "webpki"
-version = "0.22.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "f095d78192e208183081cc07bc5515ef55216397af48b873e5edcd72637fa1bd"
-dependencies = [
- "ring",
- "untrusted",
-]
-
 [[package]]
 name = "webpki-roots"
-version = "0.22.6"
+version = "0.25.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b6c71e40d7d2c34a5106301fb632274ca37242cd0c9d3e64dbece371a40a2d87"
-dependencies = [
- "webpki",
-]
+checksum = "14247bb57be4f377dfb94c72830b8ce8fc6beac03cf4bf7b9732eadd414123fc"
 
 [[package]]
 name = "which"
@@ -6328,6 +6315,16 @@ dependencies = [
  "winapi",
 ]
 
+[[package]]
+name = "winreg"
+version = "0.50.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "524e57b2c537c0f9b1e69f1965311ec12182b4122e45035b1508cd24d2adadb1"
+dependencies = [
+ "cfg-if",
+ "windows-sys 0.48.0",
+]
+
 [[package]]
 name = "winres"
 version = "0.1.12"
diff --git a/Cargo.toml b/Cargo.toml
index bc43c9fcdb..287d808bb0 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -115,11 +115,14 @@ prost-build = "0.11"
 rand = "=0.8.5"
 regex = "^1.7.0"
 lazy-regex = "2.5.0"
-reqwest = { version = "0.11.18", default-features = false, features = ["rustls-tls", "stream", "gzip", "brotli", "socks", "json"] }
+reqwest = { version = "0.11.20", default-features = false, features = ["rustls-tls", "stream", "gzip", "brotli", "socks", "json"] }
 ring = "=0.16.20"
 rusqlite = { version = "=0.29.0", features = ["unlock_notify", "bundled"] }
 rustls = "0.21.0"
 rustls-pemfile = "1.0.0"
+rustls-webpki = "0.101.4"
+rustls-native-certs = "0.6.2"
+webpki-roots = "0.25.2"
 serde = { version = "1.0.149", features = ["derive"] }
 serde_bytes = "0.11"
 serde_json = "1.0.85"
diff --git a/cli/args/mod.rs b/cli/args/mod.rs
index 424a7dc706..f82ed9a712 100644
--- a/cli/args/mod.rs
+++ b/cli/args/mod.rs
@@ -486,8 +486,8 @@ pub fn get_root_cert_store(
   for store in ca_stores.iter() {
     match store.as_str() {
       "mozilla" => {
-        root_cert_store.add_server_trust_anchors(
-          webpki_roots::TLS_SERVER_ROOTS.0.iter().map(|ta| {
+        root_cert_store.add_trust_anchors(
+          webpki_roots::TLS_SERVER_ROOTS.iter().map(|ta| {
             rustls::OwnedTrustAnchor::from_subject_spki_name_constraints(
               ta.subject,
               ta.spki,
diff --git a/ext/tls/Cargo.toml b/ext/tls/Cargo.toml
index 4dfc045f68..a06af68acf 100644
--- a/ext/tls/Cargo.toml
+++ b/ext/tls/Cargo.toml
@@ -17,8 +17,8 @@ path = "lib.rs"
 deno_core.workspace = true
 once_cell.workspace = true
 rustls = { workspace = true, features = ["dangerous_configuration"] }
-rustls-native-certs = "0.6.2"
+rustls-native-certs.workspace = true
 rustls-pemfile.workspace = true
+rustls-webpki.workspace = true
 serde.workspace = true
-webpki = "0.22"
-webpki-roots = "0.22"
+webpki-roots.workspace = true
diff --git a/ext/tls/lib.rs b/ext/tls/lib.rs
index dded1b3859..78ad243c1a 100644
--- a/ext/tls/lib.rs
+++ b/ext/tls/lib.rs
@@ -145,15 +145,15 @@ pub struct BasicAuth {
 pub fn create_default_root_cert_store() -> RootCertStore {
   let mut root_cert_store = RootCertStore::empty();
   // TODO(@justinmchase): Consider also loading the system keychain here
-  root_cert_store.add_server_trust_anchors(
-    webpki_roots::TLS_SERVER_ROOTS.0.iter().map(|ta| {
+  root_cert_store.add_trust_anchors(webpki_roots::TLS_SERVER_ROOTS.iter().map(
+    |ta| {
       rustls::OwnedTrustAnchor::from_subject_spki_name_constraints(
         ta.subject,
         ta.spki,
         ta.name_constraints,
       )
-    }),
-  );
+    },
+  ));
   root_cert_store
 }
 
@@ -187,7 +187,7 @@ pub fn create_client_config(
     let client =
       if let Some((cert_chain, private_key)) = maybe_cert_chain_and_key {
         client_config
-          .with_single_cert(cert_chain, private_key)
+          .with_client_auth_cert(cert_chain, private_key)
           .expect("invalid client key or certificate")
       } else {
         client_config.with_no_client_auth()
@@ -223,7 +223,7 @@ pub fn create_client_config(
   let client = if let Some((cert_chain, private_key)) = maybe_cert_chain_and_key
   {
     client_config
-      .with_single_cert(cert_chain, private_key)
+      .with_client_auth_cert(cert_chain, private_key)
       .expect("invalid client key or certificate")
   } else {
     client_config.with_no_client_auth()