diff --git a/CHANGELOG.md b/CHANGELOG.md
index 236696662..bba8be2b6 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,33 @@
 # Changelog
 
+## v1.19.7
+
+- ### Fixes
+
+  - **Check for updates in the foreground, not the background - [jyn514], [pull/2166]**
+
+    This avoids creating a new OpenSSL context while the main thread exits the process.
+
+    [jyn514]: https://github.com/jyn514
+    [pull/2166]: https://github.com/cloudflare/wrangler/pull/2166
+
+  - **fix cli help typo - [saikatdas0790], [pull/2160]**
+
+    [saikatdas0790]: https://github.com/saikatdas0790
+    [pull/2160]: https://github.com/cloudflare/wrangler/pull/2160
+
+  - **Improve heuristic for --openssl-legacy-provider (#2155) - [eagleflo], [pull/2172]**
+
+    Improve the heuristic for detecting whether we need `--openssl-legacy-provider` added in #2116 by also checking whether the Node.js was actually built against OpenSSL 3 and has that option available.
+
+    [eagleflo]: https://github.com/eagleflo
+    [pull/2172]: https://github.com/cloudflare/wrangler/pull/2172
+
+  - **Revert "Don't look for background updates unless Wrangler finished successfully" - [jyn514], [pull/2165]**
+
+    [jyn514]: https://github.com/jyn514
+    [pull/2165]: https://github.com/cloudflare/wrangler/pull/2165
+
 ## v1.19.6
 
 - ### Features
diff --git a/Cargo.lock b/Cargo.lock
index 2f2bc65a4..b64ed8b25 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -43,9 +43,9 @@ dependencies = [
 
 [[package]]
 name = "anyhow"
-version = "1.0.51"
+version = "1.0.52"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "8b26702f315f53b6071259e15dd9d64528213b44d61de1ec926eca7715d62203"
+checksum = "84450d0b4a8bd1ba4144ce8ce718fbc5d071358b1e5384bace6536b3d1f2d5b3"
 dependencies = [
  "backtrace",
 ]
@@ -753,9 +753,9 @@ dependencies = [
 
 [[package]]
 name = "erased-serde"
-version = "0.3.16"
+version = "0.3.17"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "3de9ad4541d99dc22b59134e7ff8dc3d6c988c89ecd7324bf10a8362b07a2afa"
+checksum = "44a5d80251b806a14cd3e4e1a582e912d5cbf6904ab19fdefbd7a56adca088e1"
 dependencies = [
  "serde",
 ]
@@ -915,9 +915,9 @@ checksum = "3dcaa9ae7725d12cdb85b3ad99a434db70b468c09ded17e012d86b5c1010f7a7"
 
 [[package]]
 name = "futures"
-version = "0.3.17"
+version = "0.3.19"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "a12aa0eb539080d55c3f2d45a67c3b58b6b0773c1a3ca2dfec66d58c97fd66ca"
+checksum = "28560757fe2bb34e79f907794bb6b22ae8b0e5c669b638a1132f2592b19035b4"
 dependencies = [
  "futures-channel",
  "futures-core",
@@ -930,9 +930,9 @@ dependencies = [
 
 [[package]]
 name = "futures-channel"
-version = "0.3.17"
+version = "0.3.19"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5da6ba8c3bb3c165d3c7319fc1cc8304facf1fb8db99c5de877183c08a273888"
+checksum = "ba3dda0b6588335f360afc675d0564c17a77a2bda81ca178a4b6081bd86c7f0b"
 dependencies = [
  "futures-core",
  "futures-sink",
@@ -940,15 +940,15 @@ dependencies = [
 
 [[package]]
 name = "futures-core"
-version = "0.3.17"
+version = "0.3.19"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "88d1c26957f23603395cd326b0ffe64124b818f4449552f960d815cfba83a53d"
+checksum = "d0c8ff0461b82559810cdccfde3215c3f373807f5e5232b71479bff7bb2583d7"
 
 [[package]]
 name = "futures-executor"
-version = "0.3.17"
+version = "0.3.19"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "45025be030969d763025784f7f355043dc6bc74093e4ecc5000ca4dc50d8745c"
+checksum = "29d6d2ff5bb10fb95c85b8ce46538a2e5f5e7fdc755623a7d4529ab8a4ed9d2a"
 dependencies = [
  "futures-core",
  "futures-task",
@@ -957,18 +957,16 @@ dependencies = [
 
 [[package]]
 name = "futures-io"
-version = "0.3.17"
+version = "0.3.19"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "522de2a0fe3e380f1bc577ba0474108faf3f6b18321dbf60b3b9c39a75073377"
+checksum = "b1f9d34af5a1aac6fb380f735fe510746c38067c5bf16c7fd250280503c971b2"
 
 [[package]]
 name = "futures-macro"
-version = "0.3.17"
+version = "0.3.19"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "18e4a4b95cea4b4ccbcf1c5675ca7c4ee4e9e75eb79944d07defde18068f79bb"
+checksum = "6dbd947adfffb0efc70599b3ddcf7b5597bb5fa9e245eb99f62b3a5f7bb8bd3c"
 dependencies = [
- "autocfg",
- "proc-macro-hack",
  "proc-macro2",
  "quote",
  "syn",
@@ -976,23 +974,22 @@ dependencies = [
 
 [[package]]
 name = "futures-sink"
-version = "0.3.17"
+version = "0.3.19"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "36ea153c13024fe480590b3e3d4cad89a0cfacecc24577b68f86c6ced9c2bc11"
+checksum = "e3055baccb68d74ff6480350f8d6eb8fcfa3aa11bdc1a1ae3afdd0514617d508"
 
 [[package]]
 name = "futures-task"
-version = "0.3.17"
+version = "0.3.19"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "1d3d00f4eddb73e498a54394f228cd55853bdf059259e8e7bc6e69d408892e99"
+checksum = "6ee7c6485c30167ce4dfb83ac568a849fe53274c831081476ee13e0dce1aad72"
 
 [[package]]
 name = "futures-util"
-version = "0.3.17"
+version = "0.3.19"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "36568465210a3a6ee45e1f165136d68671471a501e632e9a98d96872222b5481"
+checksum = "d9b5cf40b47a271f77a8b1bec03ca09044d99d2372c0de244e66430761127164"
 dependencies = [
- "autocfg",
  "futures-channel",
  "futures-core",
  "futures-io",
@@ -1002,8 +999,6 @@ dependencies = [
  "memchr",
  "pin-project-lite",
  "pin-utils",
- "proc-macro-hack",
- "proc-macro-nested",
  "slab",
 ]
 
@@ -1120,13 +1115,13 @@ checksum = "7f24254aa9a54b5c858eaee2f5bccdb46aaf0e486a595ed5fd8f86ba55232a70"
 
 [[package]]
 name = "http"
-version = "0.2.5"
+version = "0.2.6"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "1323096b05d41827dadeaee54c9981958c0f94e670bc94ed80037d1a7b8b186b"
+checksum = "31f4c6746584866f0feabcc69893c5b51beef3831656a968ed7ae254cdc4fd03"
 dependencies = [
  "bytes 1.1.0",
  "fnv",
- "itoa 0.4.8",
+ "itoa 1.0.1",
 ]
 
 [[package]]
@@ -1644,9 +1639,9 @@ dependencies = [
 
 [[package]]
 name = "num_cpus"
-version = "1.13.0"
+version = "1.13.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "05499f3756671c15885fee9034446956fff3f243d6077b91e5767df161f766b3"
+checksum = "19e64526ebdee182341572e50e9ad03965aa510cd94427a4549448f285e957a1"
 dependencies = [
  "hermit-abi",
  "libc",
@@ -1804,18 +1799,18 @@ checksum = "d4fd5641d01c8f18a23da7b6fe29298ff4b55afcccdf78973b24cf3175fee32e"
 
 [[package]]
 name = "pin-project"
-version = "1.0.8"
+version = "1.0.10"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "576bc800220cc65dac09e99e97b08b358cfab6e17078de8dc5fee223bd2d0c08"
+checksum = "58ad3879ad3baf4e44784bc6a718a8698867bb991f8ce24d1bcbe2cfb4c3a75e"
 dependencies = [
  "pin-project-internal",
 ]
 
 [[package]]
 name = "pin-project-internal"
-version = "1.0.8"
+version = "1.0.10"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "6e8fe8163d14ce7f0cdac2e040116f22eac817edabff0be91e8aff7e9accf389"
+checksum = "744b6f092ba29c3650faf274db506afd39944f48420f6c86b17cfe0ee1cb36bb"
 dependencies = [
  "proc-macro2",
  "quote",
@@ -1824,9 +1819,9 @@ dependencies = [
 
 [[package]]
 name = "pin-project-lite"
-version = "0.2.7"
+version = "0.2.8"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "8d31d11c69a6b52a174b42bdc0c30e5e11670f90788b2c471c31c1d17d449443"
+checksum = "e280fbe77cc62c91527259e9442153f4688736748d24660126286329742b4c6c"
 
 [[package]]
 name = "pin-utils"
@@ -1856,9 +1851,9 @@ dependencies = [
 
 [[package]]
 name = "ppv-lite86"
-version = "0.2.15"
+version = "0.2.16"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "ed0cfbc8191465bed66e1718596ee0b0b35d5ee1f41c5df2189d0fe8bde535ba"
+checksum = "eb9f9e6e233e5c4a35559a617bf40a4ec447db2e84c20b55a6f83167b7e57872"
 
 [[package]]
 name = "predicates"
@@ -1928,32 +1923,20 @@ dependencies = [
  "version_check",
 ]
 
-[[package]]
-name = "proc-macro-hack"
-version = "0.5.19"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "dbf0c48bc1d91375ae5c3cd81e3722dff1abcf81a30960240640d223f59fe0e5"
-
-[[package]]
-name = "proc-macro-nested"
-version = "0.1.7"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "bc881b2c22681370c6a780e47af9840ef841837bc98118431d4e1868bd0c1086"
-
 [[package]]
 name = "proc-macro2"
-version = "1.0.34"
+version = "1.0.36"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "2f84e92c0f7c9d58328b85a78557813e4bd845130db68d7184635344399423b1"
+checksum = "c7342d5883fbccae1cc37a2353b09c87c9b0f3afd73f5fb9bba687a1f733b029"
 dependencies = [
  "unicode-xid",
 ]
 
 [[package]]
 name = "quote"
-version = "1.0.10"
+version = "1.0.14"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "38bc8cc6a5f2e3655e0899c1b848643b2562f853f114bfec7be120678e3ace05"
+checksum = "47aa80447ce4daf1717500037052af176af5d38cc3e571d9ec1c7353fc10c87d"
 dependencies = [
  "proc-macro2",
 ]
@@ -2109,9 +2092,9 @@ dependencies = [
 
 [[package]]
 name = "reqwest"
-version = "0.11.7"
+version = "0.11.8"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "07bea77bc708afa10e59905c3d4af7c8fd43c9214251673095ff8b14345fcbc5"
+checksum = "7c4e0a76dc12a116108933f6301b95e83634e0c47b0afbed6abbaa0601e99258"
 dependencies = [
  "base64",
  "bytes 1.1.0",
@@ -2202,7 +2185,7 @@ dependencies = [
  "log",
  "ring",
  "sct",
- "webpki 0.22.0",
+ "webpki",
 ]
 
 [[package]]
@@ -2304,18 +2287,18 @@ checksum = "568a8e6258aa33c13358f81fd834adb854c6f7c9468520910a9b1e8fac068012"
 
 [[package]]
 name = "serde"
-version = "1.0.131"
+version = "1.0.133"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b4ad69dfbd3e45369132cc64e6748c2d65cdfb001a2b1c232d128b4ad60561c1"
+checksum = "97565067517b60e2d1ea8b268e59ce036de907ac523ad83a0475da04e818989a"
 dependencies = [
  "serde_derive",
 ]
 
 [[package]]
 name = "serde_derive"
-version = "1.0.131"
+version = "1.0.133"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b710a83c4e0dff6a3d511946b95274ad9ca9e5d3ae497b63fda866ac955358d2"
+checksum = "ed201699328568d8d08208fdd080e3ff594e6c422e438b6705905da01005d537"
 dependencies = [
  "proc-macro2",
  "quote",
@@ -2324,9 +2307,9 @@ dependencies = [
 
 [[package]]
 name = "serde_json"
-version = "1.0.73"
+version = "1.0.74"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "bcbd0344bc6533bc7ec56df11d42fb70f1b912351c0825ccb7211b59d8af7cf5"
+checksum = "ee2bb9cd061c5865d345bb02ca49fcef1391741b672b54a0bf7b679badec3142"
 dependencies = [
  "itoa 1.0.1",
  "ryu",
@@ -2590,9 +2573,9 @@ dependencies = [
 
 [[package]]
 name = "syn"
-version = "1.0.82"
+version = "1.0.84"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "8daf5dd0bb60cbd4137b1b587d2fc0ae729bc07cf01cd70b36a1ed5ade3b9d59"
+checksum = "ecb2e6da8ee5eb9a61068762a32fa9619cc591ceb055b3687f4cd4051ec2e06b"
 dependencies = [
  "proc-macro2",
  "quote",
@@ -2850,13 +2833,13 @@ dependencies = [
 
 [[package]]
 name = "tokio-rustls"
-version = "0.23.1"
+version = "0.23.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "4baa378e417d780beff82bf54ceb0d195193ea6a00c14e22359e7f39456b5689"
+checksum = "a27d5f2b839802bd8267fa19b0530f5a08b9c08cd417976be2a65d130fe1c11b"
 dependencies = [
  "rustls",
  "tokio",
- "webpki 0.22.0",
+ "webpki",
 ]
 
 [[package]]
@@ -2993,9 +2976,9 @@ dependencies = [
 
 [[package]]
 name = "twox-hash"
-version = "1.6.1"
+version = "1.6.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "1f559b464de2e2bdabcac6a210d12e9b5a5973c251e102c44c585c71d51bd78e"
+checksum = "4ee73e6e4924fe940354b8d4d98cad5231175d615cd855b758adc658c0aac6a0"
 dependencies = [
  "cfg-if 1.0.0",
  "rand 0.8.4",
@@ -3004,9 +2987,9 @@ dependencies = [
 
 [[package]]
 name = "typenum"
-version = "1.14.0"
+version = "1.15.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b63708a265f51345575b27fe43f9500ad611579e764c79edbc2037b1121959ec"
+checksum = "dcf81ac59edc17cc8697ff311e8f5ef2d99fcbd9817b34cec66f90b6c3dfd987"
 
 [[package]]
 name = "uname"
@@ -3114,9 +3097,9 @@ checksum = "f1bddf1187be692e79c5ffeab891132dfb0f236ed36a43c7ed39f1165ee20191"
 
 [[package]]
 name = "version_check"
-version = "0.9.3"
+version = "0.9.4"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5fecdca9a5291cc2b8dcf7dc02453fee791a280f3743cb0905f8822ae463b3fe"
+checksum = "49874b5167b65d7193b8aba1567f5c7d93d001cafc34600cee003eda787e483f"
 
 [[package]]
 name = "wait-timeout"
@@ -3236,16 +3219,6 @@ dependencies = [
  "wasm-bindgen",
 ]
 
-[[package]]
-name = "webpki"
-version = "0.21.4"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b8e38c0608262c46d4a56202ebabdeb094cef7e560ca7a226c6bf055188aa4ea"
-dependencies = [
- "ring",
- "untrusted",
-]
-
 [[package]]
 name = "webpki"
 version = "0.22.0"
@@ -3258,11 +3231,11 @@ dependencies = [
 
 [[package]]
 name = "webpki-roots"
-version = "0.21.1"
+version = "0.22.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "aabe153544e473b775453675851ecc86863d2a81d786d741f6b76778f2a48940"
+checksum = "552ceb903e957524388c4d3475725ff2c8b7960922063af6ce53c9a43da07449"
 dependencies = [
- "webpki 0.21.4",
+ "webpki",
 ]
 
 [[package]]
@@ -3330,7 +3303,7 @@ dependencies = [
 
 [[package]]
 name = "wrangler"
-version = "1.19.6"
+version = "1.19.7"
 dependencies = [
  "anyhow",
  "assert_cmd",
diff --git a/Cargo.toml b/Cargo.toml
index 7dcd47432..8628e3af5 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -1,6 +1,6 @@
 [package]
 name = "wrangler"
-version = "1.19.6"
+version = "1.19.7"
 authors = ["The Wrangler Team <wrangler@cloudflare.com>"]
 edition = "2018"
 license = "MIT/Apache-2.0"
diff --git a/npm/npm-shrinkwrap.json b/npm/npm-shrinkwrap.json
index 2378764ef..3dd305b8a 100644
--- a/npm/npm-shrinkwrap.json
+++ b/npm/npm-shrinkwrap.json
@@ -1,12 +1,12 @@
 {
   "name": "@cloudflare/wrangler",
-  "version": "1.19.6",
+  "version": "1.19.7",
   "lockfileVersion": 2,
   "requires": true,
   "packages": {
     "": {
       "name": "@cloudflare/wrangler",
-      "version": "1.19.6",
+      "version": "1.19.7",
       "hasInstallScript": true,
       "license": "MIT OR Apache-2.0",
       "dependencies": {
diff --git a/npm/package.json b/npm/package.json
index a5843c967..2dbf47255 100644
--- a/npm/package.json
+++ b/npm/package.json
@@ -1,6 +1,6 @@
 {
   "name": "@cloudflare/wrangler",
-  "version": "1.19.6",
+  "version": "1.19.7",
   "description": "Command-line interface for all things Cloudflare Workers",
   "main": "binary.js",
   "scripts": {