diff --git a/CHANGELOG.md b/CHANGELOG.md
index 650951c6..b818c240 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -7,6 +7,8 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ## [Unreleased]
 
+Updated dependencies.  Some had breaking changes: k256 0.11, pkcs 0.9, and sec1 0.3.
+
 ## [0.16.0] - 2022-04-28
 
 Added `ReqwestHttpReplicaV2Transport::create_with_client`.
diff --git a/Cargo.lock b/Cargo.lock
index b88341a2..3226ae58 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -34,9 +34,9 @@ dependencies = [
 
 [[package]]
 name = "anyhow"
-version = "1.0.56"
+version = "1.0.57"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "4361135be9122e0870de935d7c439aef945b9f9ddd4199a553b5270b49c82a27"
+checksum = "08f9b8508dccb7687a1d6c4ce66b2b0ecef467c94667de27d8d7fe1f8d2a9cdc"
 dependencies = [
  "backtrace",
 ]
@@ -96,15 +96,15 @@ checksum = "d468802bab17cbc0cc575e9b053f41e72aa36bfa6b7f55e3529ffa43161b97fa"
 
 [[package]]
 name = "backtrace"
-version = "0.3.64"
+version = "0.3.65"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5e121dee8023ce33ab248d9ce1493df03c3b38a659b240096fcbd7048ff9c31f"
+checksum = "11a17d453482a265fd5f8479f2a3f405566e6ca627837aaddb85af8b1ab8ef61"
 dependencies = [
  "addr2line",
  "cc",
  "cfg-if",
  "libc",
- "miniz_oxide 0.4.4",
+ "miniz_oxide",
  "object",
  "rustc-demangle",
 ]
@@ -285,16 +285,16 @@ dependencies = [
 
 [[package]]
 name = "clap"
-version = "3.1.8"
+version = "3.1.18"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "71c47df61d9e16dc010b55dba1952a57d8c215dbb533fd13cdd13369aac73b1c"
+checksum = "d2dbdf4bdacb33466e854ce889eee8dfd5729abf7ccd7664d0a2d60cd384440b"
 dependencies = [
  "atty",
  "bitflags",
  "clap_derive",
+ "clap_lex",
  "indexmap",
  "lazy_static",
- "os_str_bytes",
  "strsim",
  "termcolor",
  "textwrap",
@@ -302,9 +302,9 @@ dependencies = [
 
 [[package]]
 name = "clap_derive"
-version = "3.1.7"
+version = "3.1.18"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "a3aab4734e083b809aaf5794e14e756d1c798d2c69c7f7de7a09a2f5214993c1"
+checksum = "25320346e922cffe59c0bbc5410c8d8784509efb321488971081313cb1e1a33c"
 dependencies = [
  "heck",
  "proc-macro-error",
@@ -313,6 +313,15 @@ dependencies = [
  "syn",
 ]
 
+[[package]]
+name = "clap_lex"
+version = "0.2.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "a37c35f1112dad5e6e0b1adaff798507497a18fceeb30cceb3bae7d1427b9213"
+dependencies = [
+ "os_str_bytes",
+]
+
 [[package]]
 name = "codespan-reporting"
 version = "0.11.1"
@@ -336,9 +345,9 @@ dependencies = [
 
 [[package]]
 name = "const-oid"
-version = "0.7.1"
+version = "0.9.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e4c78c047431fee22c1a7bb92e00ad095a02a983affe4d8a72e2a2c62c1b94f3"
+checksum = "722e23542a15cea1f65d4a1419c4cfd7a26706c70871a13a04238ca3f40f1661"
 
 [[package]]
 name = "core-foundation"
@@ -382,9 +391,9 @@ checksum = "7a81dae078cea95a014a339291cec439d2f232ebe854a9d672b796c6afafa9b7"
 
 [[package]]
 name = "crypto-bigint"
-version = "0.3.2"
+version = "0.4.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "03c6a1d5fa1de37e071642dfa44ec552ca5b299adb128fab16138e24b548fd21"
+checksum = "3c65a74f1a0c03043720dd2b2746b9466727d5af63da6379af98ac9012384ee2"
 dependencies = [
  "generic-array",
  "rand_core",
@@ -402,16 +411,6 @@ dependencies = [
  "typenum",
 ]
 
-[[package]]
-name = "crypto-mac"
-version = "0.11.1"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b1d1a86f49236c215f271d40892d5fc950490551400b02ef360692c29815c714"
-dependencies = [
- "generic-array",
- "subtle",
-]
-
 [[package]]
 name = "delay"
 version = "0.3.1"
@@ -420,12 +419,13 @@ checksum = "8546bb2c80129c9c85cd2b44e160b917f34a8b7ce9f3af675502cf9960e33d62"
 
 [[package]]
 name = "der"
-version = "0.5.1"
+version = "0.6.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "6919815d73839e7ad218de758883aae3a257ba6759ce7a9992501efbb53d705c"
+checksum = "13dd2ae565c0a381dde7fade45fce95984c568bdcb4700a4fdbe3175e0380b2f"
 dependencies = [
  "const-oid",
  "pem-rfc7468",
+ "zeroize",
 ]
 
 [[package]]
@@ -451,6 +451,7 @@ checksum = "f2fb860ca6fafa5552fb6d0e816a69c8e49f0908bf524e30a90d97c85892d506"
 dependencies = [
  "block-buffer 0.10.2",
  "crypto-common",
+ "subtle",
 ]
 
 [[package]]
@@ -476,9 +477,9 @@ dependencies = [
 
 [[package]]
 name = "ecdsa"
-version = "0.13.4"
+version = "0.14.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "d0d69ae62e0ce582d56380743515fefaf1a8c70cec685d9677636d7e30ae9dc9"
+checksum = "e1e737f9eebb44576f3ee654141a789464071eb369d02c4397b32b6a79790112"
 dependencies = [
  "der",
  "elliptic-curve",
@@ -494,16 +495,19 @@ checksum = "e78d4f1cc4ae33bbfc157ed5d5a5ef3bc29227303d595861deb238fcec4e9457"
 
 [[package]]
 name = "elliptic-curve"
-version = "0.11.12"
+version = "0.12.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "25b477563c2bfed38a3b7a60964c49e058b2510ad3f12ba3483fd8f62c2306d6"
+checksum = "bdd8c93ccd534d6a9790f4455cd71e7adb53a12e9af7dd54d1e258473f100cea"
 dependencies = [
  "base16ct",
  "crypto-bigint",
  "der",
+ "digest 0.10.3",
  "ff",
  "generic-array",
  "group",
+ "pem-rfc7468",
+ "pkcs8",
  "rand_core",
  "sec1",
  "subtle",
@@ -539,9 +543,9 @@ dependencies = [
 
 [[package]]
 name = "ff"
-version = "0.11.0"
+version = "0.12.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b2958d04124b9f27f175eaeb9a9f383d026098aa837eadd8ba22c11f13a05b9e"
+checksum = "df689201f395c6b90dfe87127685f8dbfc083a5e779e613575d8bd7314300c3e"
 dependencies = [
  "rand_core",
  "subtle",
@@ -549,9 +553,9 @@ dependencies = [
 
 [[package]]
 name = "fixedbitset"
-version = "0.2.0"
+version = "0.4.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "37ab347416e802de484e4d03c7316c48f1ecb56574dfd4a46a80f173ce1de04d"
+checksum = "279fb028e20b3c4c320317955b77c5e0c9701f05a1d309905d6fc702cdc5053e"
 
 [[package]]
 name = "flate2"
@@ -562,7 +566,7 @@ dependencies = [
  "cfg-if",
  "crc32fast",
  "libc",
- "miniz_oxide 0.5.1",
+ "miniz_oxide",
 ]
 
 [[package]]
@@ -734,9 +738,9 @@ checksum = "78cc372d058dcf6d5ecd98510e7fbc9e5aec4d21de70f65fea8fecebcd881bd4"
 
 [[package]]
 name = "group"
-version = "0.11.0"
+version = "0.12.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "bc5ac374b108929de78460075f3dc439fa66df9d8fc77e8f12caa5165fcf0c89"
+checksum = "7391856def869c1c81063a03457c676fbcd419709c3dfb33d8d319de484b154d"
 dependencies = [
  "ff",
  "rand_core",
@@ -800,19 +804,18 @@ dependencies = [
 
 [[package]]
 name = "hmac"
-version = "0.11.0"
+version = "0.12.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "2a2a2320eb7ec0ebe8da8f744d7812d9fc4cb4d09344ac01898dbcb6a20ae69b"
+checksum = "6c49c37c09c17a53d937dfbb742eb3a961d65a994e6bcdcf37e7399d0cc8ab5e"
 dependencies = [
- "crypto-mac",
- "digest 0.9.0",
+ "digest 0.10.3",
 ]
 
 [[package]]
 name = "http"
-version = "0.2.6"
+version = "0.2.7"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "31f4c6746584866f0feabcc69893c5b51beef3831656a968ed7ae254cdc4fd03"
+checksum = "ff8670570af52249509a86f5e3e18a08c60b177071826898fde8997cf5f6bfbb"
 dependencies = [
  "bytes",
  "fnv",
@@ -832,9 +835,9 @@ dependencies = [
 
 [[package]]
 name = "httparse"
-version = "1.6.0"
+version = "1.7.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "9100414882e15fb7feccb4897e5f0ff0ff1ca7d1a86a23208ada4d7a18e6c6c4"
+checksum = "496ce29bb5a52785b44e0f7ca2847ae0bb839c9bd28f69acac9b99d461c0c04c"
 
 [[package]]
 name = "httpdate"
@@ -1108,9 +1111,9 @@ dependencies = [
 
 [[package]]
 name = "ipnet"
-version = "2.4.0"
+version = "2.5.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "35e70ee094dc02fd9c13fdad4940090f22dbd6ac7c9e7094a46cf0232a50bc7c"
+checksum = "879d54834c8c76457ef4293a689b2a8c59b076067ad77b15efafbb05f92a592b"
 
 [[package]]
 name = "itertools"
@@ -1138,22 +1141,21 @@ dependencies = [
 
 [[package]]
 name = "k256"
-version = "0.10.4"
+version = "0.11.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "19c3a5e0a0b8450278feda242592512e09f61c72e018b8cd5c859482802daf2d"
+checksum = "22588c7ced2b1dbf490ce24ea423c7fe981a78eed56ba944426fde3eb854de93"
 dependencies = [
  "cfg-if",
  "ecdsa",
  "elliptic-curve",
- "sec1",
- "sha2 0.9.9",
+ "sha2 0.10.2",
 ]
 
 [[package]]
 name = "lalrpop"
-version = "0.19.7"
+version = "0.19.8"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "852b75a095da6b69da8c5557731c3afd06525d4f655a4fc1c799e2ec8bc4dce4"
+checksum = "b30455341b0e18f276fa64540aff54deafb54c589de6aca68659c63dd2d5d823"
 dependencies = [
  "ascii-canvas",
  "atty",
@@ -1174,9 +1176,9 @@ dependencies = [
 
 [[package]]
 name = "lalrpop-util"
-version = "0.19.7"
+version = "0.19.8"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "d6d265705249fe209280676d8f68887859fa42e1d34f342fc05bd47726a5e188"
+checksum = "bcf796c978e9b4d983414f4caedc9273aa33ee214c5b887bd55fde84c85d2dc4"
 dependencies = [
  "regex",
 ]
@@ -1195,9 +1197,9 @@ checksum = "884e2677b40cc8c339eaefcb701c32ef1fd2493d71118dc0ca4b6a736c93bd67"
 
 [[package]]
 name = "libc"
-version = "0.2.122"
+version = "0.2.125"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "ec647867e2bf0772e28c8bcde4f0d19a9216916e890543b5a03ed8ef27b8f259"
+checksum = "5916d2ae698f6de9bfb891ad7a8d65c09d232dc58cc4ac433c7da3b2fd84bc2b"
 
 [[package]]
 name = "libflate"
@@ -1241,9 +1243,9 @@ dependencies = [
 
 [[package]]
 name = "log"
-version = "0.4.16"
+version = "0.4.17"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "6389c490849ff5bc16be905ae24bc913a9c8892e19b2341dbc175e14c341c2b8"
+checksum = "abb12e687cfb44aa40f41fc3978ef76448f9b6038cad6aef4259d3c095a2382e"
 dependencies = [
  "cfg-if",
 ]
@@ -1280,9 +1282,9 @@ checksum = "a3e378b66a060d48947b590737b30a1be76706c8dd7b8ba0f2fe3989c68a853f"
 
 [[package]]
 name = "memchr"
-version = "2.4.1"
+version = "2.5.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "308cc39be01b73d0d18f82a0e7b2a3df85245f84af96fdddc5d202d27e47b86a"
+checksum = "2dffe52ecf27772e601905b7522cb4ef790d2cc203488bbd0e2fe85fcb74566d"
 
 [[package]]
 name = "mime"
@@ -1300,16 +1302,6 @@ dependencies = [
  "unicase",
 ]
 
-[[package]]
-name = "miniz_oxide"
-version = "0.4.4"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "a92518e98c078586bc6c934028adcca4c92a53d6a958196de835170a01d84e4b"
-dependencies = [
- "adler",
- "autocfg",
-]
-
 [[package]]
 name = "miniz_oxide"
 version = "0.5.1"
@@ -1321,25 +1313,14 @@ dependencies = [
 
 [[package]]
 name = "mio"
-version = "0.8.2"
+version = "0.8.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "52da4364ffb0e4fe33a9841a98a3f3014fb964045ce4f7a45a398243c8d6b0c9"
+checksum = "713d550d9b44d89174e066b7a6217ae06234c10cb47819a88290d2b353c31799"
 dependencies = [
  "libc",
  "log",
- "miow",
- "ntapi",
  "wasi 0.11.0+wasi-snapshot-preview1",
- "winapi",
-]
-
-[[package]]
-name = "miow"
-version = "0.3.7"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b9f1c5b025cda876f66ef43a113f91ebc9f4ccef34843000e0adf6ebbab84e21"
-dependencies = [
- "winapi",
+ "windows-sys",
 ]
 
 [[package]]
@@ -1384,15 +1365,6 @@ version = "1.0.4"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "e4a24736216ec316047a1fc4252e27dabb04218aa4a3f37c6e7ddbf1f9782b54"
 
-[[package]]
-name = "ntapi"
-version = "0.3.7"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "c28774a7fd2fbb4f0babd8237ce554b73af68021b5f695a3cebd6c59bac0980f"
-dependencies = [
- "winapi",
-]
-
 [[package]]
 name = "num-bigint"
 version = "0.2.6"
@@ -1417,9 +1389,9 @@ dependencies = [
 
 [[package]]
 name = "num-integer"
-version = "0.1.44"
+version = "0.1.45"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "d2cc698a63b549a70bc047073d2949cce27cd1c7b0a4a862d08a8031bc2801db"
+checksum = "225d3389fb3509a24c93f5c29eb6bde2586b98d9f016636dff58d7c6f7569cd9"
 dependencies = [
  "autocfg",
  "num-traits",
@@ -1427,9 +1399,9 @@ dependencies = [
 
 [[package]]
 name = "num-traits"
-version = "0.2.14"
+version = "0.2.15"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "9a64b1ec5cda2586e284722486d802acf1f7dbdc623e2bfc57e65ca1cd099290"
+checksum = "578ede34cf02f8924ab9447f50c28075b4d3e5b269972345e7e0372b38c6cdcd"
 dependencies = [
  "autocfg",
 ]
@@ -1467,18 +1439,18 @@ dependencies = [
 
 [[package]]
 name = "num_threads"
-version = "0.1.5"
+version = "0.1.6"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "aba1801fb138d8e85e11d0fc70baf4fe1cdfffda7c6cd34a854905df588e5ed0"
+checksum = "2819ce041d2ee131036f4fc9d6ae7ae125a3a40e97ba64d04fe799ad9dabbb44"
 dependencies = [
  "libc",
 ]
 
 [[package]]
 name = "object"
-version = "0.27.1"
+version = "0.28.4"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "67ac1d3f9a1d3616fd9a60c8d74296f22406a238b6a72f5cc1e6f314df4ffbf9"
+checksum = "e42c982f2d955fac81dd7e1d0e1426a7d702acd9c98d19ab01083a6a0328c424"
 dependencies = [
  "memchr",
 ]
@@ -1497,18 +1469,30 @@ checksum = "624a8340c38c1b80fd549087862da4ba43e08858af025b236e509b6649fc13d5"
 
 [[package]]
 name = "openssl"
-version = "0.10.38"
+version = "0.10.40"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "0c7ae222234c30df141154f159066c5093ff73b63204dcda7121eb082fc56a95"
+checksum = "fb81a6430ac911acb25fe5ac8f1d2af1b4ea8a4fdfda0f1ee4292af2e2d8eb0e"
 dependencies = [
  "bitflags",
  "cfg-if",
  "foreign-types",
  "libc",
  "once_cell",
+ "openssl-macros",
  "openssl-sys",
 ]
 
+[[package]]
+name = "openssl-macros"
+version = "0.1.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "b501e44f11665960c7e7fcf062c7d96a14ade4aa98116c004b2e37b5be7d736c"
+dependencies = [
+ "proc-macro2",
+ "quote",
+ "syn",
+]
+
 [[package]]
 name = "openssl-probe"
 version = "0.1.5"
@@ -1517,9 +1501,9 @@ checksum = "ff011a302c396a5197692431fc1948019154afc178baf7d8e37367442a4601cf"
 
 [[package]]
 name = "openssl-sys"
-version = "0.9.72"
+version = "0.9.73"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "7e46109c383602735fa0a2e48dd2b7c892b048e1bf69e5c3b1d804b7d9c203cb"
+checksum = "9d5fd19fb3e0a8191c1e34935718976a3e70c112ab9a24af6d7cadccd9d90bc0"
 dependencies = [
  "autocfg",
  "cc",
@@ -1533,9 +1517,6 @@ name = "os_str_bytes"
 version = "6.0.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "8e22443d1643a904602595ba1cd8f7d896afe56d26712531c5ff73a15b2fbf64"
-dependencies = [
- "memchr",
-]
 
 [[package]]
 name = "parking_lot"
@@ -1555,7 +1536,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "87f5ec2493a61ac0506c0f4199f99070cbe83857b0337006a30f3e6719b8ef58"
 dependencies = [
  "lock_api",
- "parking_lot_core 0.9.2",
+ "parking_lot_core 0.9.3",
 ]
 
 [[package]]
@@ -1574,9 +1555,9 @@ dependencies = [
 
 [[package]]
 name = "parking_lot_core"
-version = "0.9.2"
+version = "0.9.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "995f667a6c822200b0433ac218e05582f0e2efa1b922a3fd2fbaadc5f87bab37"
+checksum = "09a279cbf25cb0757810394fbc1e359949b59e348145c643a939a525692e6929"
 dependencies = [
  "cfg-if",
  "libc",
@@ -1602,9 +1583,9 @@ dependencies = [
 
 [[package]]
 name = "pem-rfc7468"
-version = "0.3.1"
+version = "0.6.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "01de5d978f34aa4b2296576379fcc416034702fd94117c56ffd8a1a767cefb30"
+checksum = "24d159833a9105500e0398934e205e0773f0b27529557134ecfc51c27646adac"
 dependencies = [
  "base64ct",
 ]
@@ -1617,9 +1598,9 @@ checksum = "d4fd5641d01c8f18a23da7b6fe29298ff4b55afcccdf78973b24cf3175fee32e"
 
 [[package]]
 name = "petgraph"
-version = "0.5.1"
+version = "0.6.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "467d164a6de56270bd7c4d070df81d07beace25012d5103ced4e9ff08d6afdb7"
+checksum = "4a13a2fa9d0b63e5f22328828741e523766fff0ee9e779316902290dff3f824f"
 dependencies = [
  "fixedbitset",
  "indexmap",
@@ -1642,9 +1623,9 @@ checksum = "db8bcd96cb740d03149cbad5518db9fd87126a10ab519c011893b1754134c468"
 
 [[package]]
 name = "pin-project-lite"
-version = "0.2.8"
+version = "0.2.9"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e280fbe77cc62c91527259e9442153f4688736748d24660126286329742b4c6c"
+checksum = "e0a7ae3ac2f1173085d398531c705756c94a4c56843785df85a60c1a0afac116"
 
 [[package]]
 name = "pin-utils"
@@ -1664,13 +1645,12 @@ dependencies = [
 
 [[package]]
 name = "pkcs8"
-version = "0.8.0"
+version = "0.9.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "7cabda3fb821068a9a4fab19a683eac3af12edf0f34b94a8be53c4972b8149d0"
+checksum = "9eca2c590a5f85da82668fa685c09ce2888b9430e83299debf1f34b65fd4a4ba"
 dependencies = [
  "der",
  "spki",
- "zeroize",
 ]
 
 [[package]]
@@ -1737,9 +1717,9 @@ dependencies = [
 
 [[package]]
 name = "proc-macro2"
-version = "1.0.37"
+version = "1.0.38"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "ec757218438d5fda206afc041538b2f6d889286160d649a86a24d37e1235afd1"
+checksum = "9027b48e9d4c9175fa2218adf3557f91c1137021739951d4932f5f8268ac48aa"
 dependencies = [
  "unicode-xid",
 ]
@@ -1787,9 +1767,9 @@ dependencies = [
 
 [[package]]
 name = "quote"
-version = "1.0.17"
+version = "1.0.18"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "632d02bff7f874a36f33ea8bb416cd484b90cc66c1194b1a1110d067a7013f58"
+checksum = "a1feb54ed693b93a84e14094943b84b7c4eae204c512b7ccb95ab0c66d278ad1"
 dependencies = [
  "proc-macro2",
 ]
@@ -1938,9 +1918,9 @@ dependencies = [
 
 [[package]]
 name = "rfc6979"
-version = "0.1.0"
+version = "0.2.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "96ef608575f6392792f9ecf7890c00086591d29a83910939d430753f7c050525"
+checksum = "6c0788437d5ee113c49af91d3594ebc4fcdcc962f8b6df5aa1c3eeafd8ad95de"
 dependencies = [
  "crypto-bigint",
  "hmac",
@@ -1988,30 +1968,30 @@ dependencies = [
 
 [[package]]
 name = "rustls-native-certs"
-version = "0.6.1"
+version = "0.6.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5ca9ebdfa27d3fc180e42879037b5338ab1c040c06affd00d8338598e7800943"
+checksum = "0167bac7a9f490495f3c33013e7722b53cb087ecbe082fb0c6387c96f634ea50"
 dependencies = [
  "openssl-probe",
- "rustls-pemfile 0.2.1",
+ "rustls-pemfile 1.0.0",
  "schannel",
  "security-framework",
 ]
 
 [[package]]
 name = "rustls-pemfile"
-version = "0.2.1"
+version = "0.3.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5eebeaeb360c87bfb72e84abdb3447159c0eaececf1bef2aecd65a8be949d1c9"
+checksum = "1ee86d63972a7c661d1536fefe8c3c8407321c3df668891286de28abcd087360"
 dependencies = [
  "base64",
 ]
 
 [[package]]
 name = "rustls-pemfile"
-version = "0.3.0"
+version = "1.0.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "1ee86d63972a7c661d1536fefe8c3c8407321c3df668891286de28abcd087360"
+checksum = "e7522c9de787ff061458fe9a829dc790a3f5b22dc571694fc5883f448b94d9a9"
 dependencies = [
  "base64",
 ]
@@ -2077,10 +2057,11 @@ dependencies = [
 
 [[package]]
 name = "sec1"
-version = "0.2.1"
+version = "0.3.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "08da66b8b0965a5555b6bd6639e68ccba85e1e2506f5fbb089e93f8a04e1a2d1"
+checksum = "3be24c1842290c45df0a7bf069e0c268a747ad05a192f2fd7dcfdbc1cba40928"
 dependencies = [
+ "base16ct",
  "der",
  "generic-array",
  "pkcs8",
@@ -2113,24 +2094,24 @@ dependencies = [
 
 [[package]]
 name = "semver"
-version = "1.0.7"
+version = "1.0.9"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "d65bd28f48be7196d222d95b9243287f48d27aca604e08497513019ff0502cc4"
+checksum = "8cb243bdfdb5936c8dc3c45762a19d12ab4550cdc753bc247637d4ec35a040fd"
 
 [[package]]
 name = "serde"
-version = "1.0.136"
+version = "1.0.137"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "ce31e24b01e1e524df96f1c2fdd054405f8d7376249a5110886fb4b658484789"
+checksum = "61ea8d54c77f8315140a05f4c7237403bf38b72704d031543aa1d16abbf517d1"
 dependencies = [
  "serde_derive",
 ]
 
 [[package]]
 name = "serde_bytes"
-version = "0.11.5"
+version = "0.11.6"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "16ae07dd2f88a366f15bd0632ba725227018c69a1c8550a927324f8eb8368bb9"
+checksum = "212e73464ebcde48d723aa02eb270ba62eff38a9b732df31f33f1b4e145f3a54"
 dependencies = [
  "serde",
 ]
@@ -2147,9 +2128,9 @@ dependencies = [
 
 [[package]]
 name = "serde_derive"
-version = "1.0.136"
+version = "1.0.137"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "08597e7152fcd306f41838ed3e37be9eaeed2b61c42e2117266a554fab4662f9"
+checksum = "1f26faba0c3959972377d3b2d306ee9f71faee9714294e41bb777f83f88578be"
 dependencies = [
  "proc-macro2",
  "quote",
@@ -2158,9 +2139,9 @@ dependencies = [
 
 [[package]]
 name = "serde_json"
-version = "1.0.79"
+version = "1.0.81"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "8e8d9fa5c3b304765ce1fd9c4c8a3de2c8db365a5b91be52f186efc675681d95"
+checksum = "9b7ce2b32a1aed03c558dc61a5cd328f15aff2dbc17daad8fb8af04d2100e15c"
 dependencies = [
  "itoa",
  "ryu",
@@ -2214,11 +2195,11 @@ dependencies = [
 
 [[package]]
 name = "signature"
-version = "1.4.0"
+version = "1.5.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "02658e48d89f2bec991f9a78e69cfa4c316f8d6a6c4ec12fae1aeb263d486788"
+checksum = "f054c6c1a6e95179d6f23ed974060dcefb2d9388bb7256900badad682c499de4"
 dependencies = [
- "digest 0.9.0",
+ "digest 0.10.3",
  "rand_core",
 ]
 
@@ -2276,9 +2257,9 @@ checksum = "6e63cff320ae2c57904679ba7cb63280a3dc4613885beafb148ee7bf9aa9042d"
 
 [[package]]
 name = "spki"
-version = "0.5.4"
+version = "0.6.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "44d01ac02a6ccf3e07db148d2be087da624fea0221a16152ed01f0496a6b0a27"
+checksum = "67cf02bbac7a337dc36e4f5a693db6c21e7863f45070f7064577eb4367a3212b"
 dependencies = [
  "base64ct",
  "der",
@@ -2330,9 +2311,9 @@ checksum = "6bdef32e8150c2a081110b42772ffe7d7c9032b606bc226c8260fd97e0976601"
 
 [[package]]
 name = "syn"
-version = "1.0.91"
+version = "1.0.93"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b683b2b825c8eef438b77c36a06dc262294da3d5a5813fac20da149241dcd44d"
+checksum = "04066589568b72ec65f42d65a1a52436e954b168773148893c020269563decf2"
 dependencies = [
  "proc-macro2",
  "quote",
@@ -2381,18 +2362,18 @@ checksum = "b1141d4d61095b28419e22cb0bbf02755f5e54e0526f97f1e3d1d160e60885fb"
 
 [[package]]
 name = "thiserror"
-version = "1.0.30"
+version = "1.0.31"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "854babe52e4df1653706b98fcfc05843010039b406875930a70e4d9644e5c417"
+checksum = "bd829fe32373d27f76265620b5309d0340cb8550f523c1dda251d6298069069a"
 dependencies = [
  "thiserror-impl",
 ]
 
 [[package]]
 name = "thiserror-impl"
-version = "1.0.30"
+version = "1.0.31"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "aa32fd3f627f367fe16f893e2597ae3c05020f8bba2666a4e6ea73d377e5714b"
+checksum = "0396bc89e626244658bef819e22d0cc459e795a5ebe878e6ec336d1674a8d79a"
 dependencies = [
  "proc-macro2",
  "quote",
@@ -2440,9 +2421,9 @@ dependencies = [
 
 [[package]]
 name = "tinyvec"
-version = "1.5.1"
+version = "1.6.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "2c1c1d5a42b6245520c249549ec267180beaffcc0615401ac8e31853d4b6d8d2"
+checksum = "87cc5ceb3875bb20c2890005a4e226a4651264a5c75edb2421b52861a0a0cb50"
 dependencies = [
  "tinyvec_macros",
 ]
@@ -2455,9 +2436,9 @@ checksum = "cda74da7e1a664f795bb1f8a87ec406fb89a02522cf6e50620d016add6dbbf5c"
 
 [[package]]
 name = "tokio"
-version = "1.17.0"
+version = "1.18.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "2af73ac49756f3f7c01172e34a23e5d0216f6c32333757c2c61feb2bbff5a5ee"
+checksum = "4903bf0427cf68dddd5aa6a93220756f8be0c34fcfa9f5e6191e103e15a31395"
 dependencies = [
  "bytes",
  "libc",
@@ -2496,9 +2477,9 @@ dependencies = [
 
 [[package]]
 name = "tokio-rustls"
-version = "0.23.3"
+version = "0.23.4"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "4151fda0cf2798550ad0b34bcfc9b9dcc2a9d2471c895c68f3a8818e54f2389e"
+checksum = "c43ee83903113e03984cb9e5cebe6c04a5116269e900e3ddba8f068a62adda59"
 dependencies = [
  "rustls",
  "tokio",
@@ -2521,9 +2502,9 @@ dependencies = [
 
 [[package]]
 name = "toml"
-version = "0.5.8"
+version = "0.5.9"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "a31142970826733df8241ef35dc040ef98c679ab14d7c3e54d827099b3acecaa"
+checksum = "8d82e1a7758622a465f8cee077614c73484dac5b836c02ff6a40d5d1010324d7"
 dependencies = [
  "serde",
 ]
@@ -2536,9 +2517,9 @@ checksum = "360dfd1d6d30e05fda32ace2c8c70e9c0a9da713275777f5a4dbb8a1893930c6"
 
 [[package]]
 name = "tracing"
-version = "0.1.32"
+version = "0.1.34"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "4a1bdf54a7c28a2bbf701e1d2233f6c77f473486b94bee4f9678da5a148dca7f"
+checksum = "5d0ecdcb44a79f0fe9844f0c4f33a342cbcbb5117de8001e6ba0dc2351327d09"
 dependencies = [
  "cfg-if",
  "pin-project-lite",
@@ -2548,9 +2529,9 @@ dependencies = [
 
 [[package]]
 name = "tracing-attributes"
-version = "0.1.20"
+version = "0.1.21"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "2e65ce065b4b5c53e73bb28912318cb8c9e9ad3921f1d669eb0e68b4c8143a2b"
+checksum = "cc6b8ad3567499f98a1db7a752b07a7c8c7c7c34c332ec00effb2b0027974b7c"
 dependencies = [
  "proc-macro2",
  "quote",
@@ -2559,9 +2540,9 @@ dependencies = [
 
 [[package]]
 name = "tracing-core"
-version = "0.1.24"
+version = "0.1.26"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "90442985ee2f57c9e1b548ee72ae842f4a9a20e3f417cc38dbc5dc684d9bb4ee"
+checksum = "f54c8ca710e81886d498c2fd3331b56c93aa248d49de2222ad2742247c60072f"
 dependencies = [
  "lazy_static",
 ]
@@ -2595,9 +2576,9 @@ dependencies = [
 
 [[package]]
 name = "unicode-bidi"
-version = "0.3.7"
+version = "0.3.8"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "1a01404663e3db436ed2746d9fefef640d868edae3cceb81c3b8d5732fda678f"
+checksum = "099b7128301d285f79ddd55b9a83d5e6b9e97c92e0ea0daebee7263e932de992"
 
 [[package]]
 name = "unicode-normalization"
@@ -2616,9 +2597,9 @@ checksum = "3ed742d4ea2bd1176e236172c8429aaf54486e7ac098db29ffe6529e0ce50973"
 
 [[package]]
 name = "unicode-xid"
-version = "0.2.2"
+version = "0.2.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "8ccb82d61f80a663efe1f787a51b16b5a51e3314d6ac365b08639f52387b33f3"
+checksum = "957e51f3646910546462e67d5f7599b9e4fb8acdd304b087a6494730f9eebf04"
 
 [[package]]
 name = "untrusted"
@@ -2826,9 +2807,9 @@ checksum = "712e227841d057c1ee1cd2fb22fa7e5a5461ae8e48fa2ca79ec42cfc1931183f"
 
 [[package]]
 name = "windows-sys"
-version = "0.34.0"
+version = "0.36.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5acdd78cb4ba54c0045ac14f62d8f94a03d10047904ae2a40afa1e99d8f70825"
+checksum = "ea04155a16a59f9eab786fe12a4a450e75cdb175f9e0d80da1e17db09f55b8d2"
 dependencies = [
  "windows_aarch64_msvc",
  "windows_i686_gnu",
@@ -2839,33 +2820,33 @@ dependencies = [
 
 [[package]]
 name = "windows_aarch64_msvc"
-version = "0.34.0"
+version = "0.36.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "17cffbe740121affb56fad0fc0e421804adf0ae00891205213b5cecd30db881d"
+checksum = "9bb8c3fd39ade2d67e9874ac4f3db21f0d710bee00fe7cab16949ec184eeaa47"
 
 [[package]]
 name = "windows_i686_gnu"
-version = "0.34.0"
+version = "0.36.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "2564fde759adb79129d9b4f54be42b32c89970c18ebf93124ca8870a498688ed"
+checksum = "180e6ccf01daf4c426b846dfc66db1fc518f074baa793aa7d9b9aaeffad6a3b6"
 
 [[package]]
 name = "windows_i686_msvc"
-version = "0.34.0"
+version = "0.36.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "9cd9d32ba70453522332c14d38814bceeb747d80b3958676007acadd7e166956"
+checksum = "e2e7917148b2812d1eeafaeb22a97e4813dfa60a3f8f78ebe204bcc88f12f024"
 
 [[package]]
 name = "windows_x86_64_gnu"
-version = "0.34.0"
+version = "0.36.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "cfce6deae227ee8d356d19effc141a509cc503dfd1f850622ec4b0f84428e1f4"
+checksum = "4dcd171b8776c41b97521e5da127a2d86ad280114807d0b2ab1e462bc764d9e1"
 
 [[package]]
 name = "windows_x86_64_msvc"
-version = "0.34.0"
+version = "0.36.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "d19538ccc21819d01deaf88d6a17eae6596a12e9aafdbb97916fb49896d89de9"
+checksum = "c811ca4a8c853ef420abd8592ba53ddbbac90410fab6903b3e79972a631f7680"
 
 [[package]]
 name = "winreg"
@@ -2878,6 +2859,6 @@ dependencies = [
 
 [[package]]
 name = "zeroize"
-version = "1.5.4"
+version = "1.5.5"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "7eb5728b8afd3f280a869ce1d4c554ffaed35f45c231fc41bfbd0381bef50317"
+checksum = "94693807d016b2f2d2e14420eb3bfcca689311ff775dcf113d74ea624b7cdf07"
diff --git a/ic-agent/Cargo.toml b/ic-agent/Cargo.toml
index 052092b8..2358e1ec 100644
--- a/ic-agent/Cargo.toml
+++ b/ic-agent/Cargo.toml
@@ -23,7 +23,7 @@ hex = "0.4.0"
 http = "0.2.6"
 hyper-rustls = { version = "0.23.0", features = [ "webpki-roots" ] }
 ic-types = "0.3.0"
-k256 = "0.10"
+k256 = { version = "0.11", features = ["pem"] }
 leb128 = "0.2.5"
 mime = "0.3.16"
 rand = "0.8.5"
@@ -36,8 +36,8 @@ sha2 = "0.10"
 simple_asn1 = "0.6.1"
 thiserror = "1.0.30"
 url = "2.1.0"
-pkcs8 = { version = "0.8", features = ["std"] }
-sec1 = { version = "0.2", features = ["pem"]}
+pkcs8 = { version = "0.9", features = ["std"] }
+sec1 = { version = "0.3", features = ["pem"]}
 
 [dependencies.reqwest]
 version = "0.11.7"
diff --git a/ic-agent/src/identity/secp256k1.rs b/ic-agent/src/identity/secp256k1.rs
index 304178d6..b79edbe9 100644
--- a/ic-agent/src/identity/secp256k1.rs
+++ b/ic-agent/src/identity/secp256k1.rs
@@ -5,11 +5,9 @@ use crate::identity::error::PemError;
 
 use k256::{
     ecdsa::{self, signature::Signer, SigningKey, VerifyingKey},
-    elliptic_curve::{sec1::ToEncodedPoint, AlgorithmParameters},
-    pkcs8::{PublicKeyDocument, SubjectPublicKeyInfo},
-    Secp256k1, SecretKey,
+    pkcs8::{Document, EncodePublicKey},
+    SecretKey,
 };
-use std::convert::TryInto;
 #[cfg(feature = "pem")]
 use std::{fs::File, io, path::Path};
 
@@ -20,7 +18,7 @@ use std::{fs::File, io, path::Path};
 pub struct Secp256k1Identity {
     private_key: SigningKey,
     _public_key: VerifyingKey,
-    der_encoded_public_key: PublicKeyDocument,
+    der_encoded_public_key: Document,
 }
 
 impl Secp256k1Identity {
@@ -33,7 +31,7 @@ impl Secp256k1Identity {
     /// Creates an identity from a PEM certificate.
     #[cfg(feature = "pem")]
     pub fn from_pem<R: io::Read>(pem_reader: R) -> Result<Self, PemError> {
-        use sec1::{pem::PemLabel, EcPrivateKeyDocument};
+        use sec1::{pem::PemLabel, EcPrivateKey};
 
         const EC_PARAMETERS: &str = "EC PARAMETERS";
         const SECP256K1: &[u8] = b"\x06\x05\x2b\x81\x04\x00\x0a";
@@ -45,7 +43,7 @@ impl Secp256k1Identity {
                 return Err(PemError::UnsupportedKeyCurve(pem.contents));
             }
 
-            if pem.tag != EcPrivateKeyDocument::TYPE_LABEL {
+            if pem.tag != EcPrivateKey::PEM_LABEL {
                 continue;
             }
             let private_key =
@@ -58,13 +56,9 @@ impl Secp256k1Identity {
     /// Creates an identity from a private key.
     pub fn from_private_key(private_key: SecretKey) -> Self {
         let public_key = private_key.public_key();
-        let public_key_bytes = public_key.to_encoded_point(false);
-        let der_encoded_public_key = SubjectPublicKeyInfo {
-            algorithm: Secp256k1::algorithm_identifier(),
-            subject_public_key: public_key_bytes.as_ref(),
-        }
-        .try_into()
-        .expect("Cannot DER encode secp256k1 public key.");
+        let der_encoded_public_key = public_key
+            .to_public_key_der()
+            .expect("Cannot DER encode secp256k1 public key.");
         Self {
             private_key: private_key.into(),
             _public_key: public_key.into(),