diff --git a/.github/workflows/breakage-against-ponyc-latest.yml b/.github/workflows/breakage-against-ponyc-latest.yml
index c64e609..f2a886d 100644
--- a/.github/workflows/breakage-against-ponyc-latest.yml
+++ b/.github/workflows/breakage-against-ponyc-latest.yml
@@ -9,7 +9,7 @@ jobs:
     name: libressl 3.x with ponyc main
     runs-on: ubuntu-latest
     container:
-      image: ghcr.io/ponylang/shared-docker-ci-x86-64-unknown-linux-builder-with-libressl-3.7.3:latest
+      image: ghcr.io/ponylang/shared-docker-ci-x86-64-unknown-linux-builder-with-libressl-3.9.1:latest
     steps:
       - uses: actions/checkout@v4.1.1
       - name: Test
diff --git a/.github/workflows/pr.yml b/.github/workflows/pr.yml
index 0600408..43d80d3 100644
--- a/.github/workflows/pr.yml
+++ b/.github/workflows/pr.yml
@@ -36,7 +36,7 @@ jobs:
     name: libressl 3.x with most recent ponyc release
     runs-on: ubuntu-latest
     container:
-      image: ghcr.io/ponylang/shared-docker-ci-x86-64-unknown-linux-builder-with-libressl-3.7.3:release
+      image: ghcr.io/ponylang/shared-docker-ci-x86-64-unknown-linux-builder-with-libressl-3.9.1:release
     steps:
       - uses: actions/checkout@v4.1.1
       - name: Test
diff --git a/.release-notes/next-release.md b/.release-notes/next-release.md
index e69de29..5595088 100644
--- a/.release-notes/next-release.md
+++ b/.release-notes/next-release.md
@@ -0,0 +1,3 @@
+## Update to LibreSSL 3.9.1 on Windows
+
+The version of LibreSSL used on Windows was updated to 3.9.1 to keep in sync with the `net_ssl` package.
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3ba6689..2ac5298 100755
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -12,6 +12,7 @@ All notable changes to this library will be documented in this file. This projec
 
 ### Changed
 
+- - Update to LibreSSL 3.9.1 on Windows ([PR #106](https://github.com/ponylang/crypto/pull/106))
 
 ## [1.2.2] - 2023-04-27
 
diff --git a/make.ps1 b/make.ps1
index 1d90be1..b245589 100644
--- a/make.ps1
+++ b/make.ps1
@@ -145,7 +145,7 @@ function BuildTest
 
 function BuildLibs
 {
-  $libreSsl = "libressl-3.7.3"
+  $libreSsl = "libressl-3.9.1"
 
   if (-not (Test-Path "$rootDir/crypto.lib"))
   {
@@ -175,7 +175,7 @@ function BuildLibs
     }
 
     # copy to the root dir (i.e. PONYPATH) for linking
-    Copy-Item -Force -Path "$libsDir/lib/crypto-50.lib" -Destination "$rootDir/crypto.lib"
+    Copy-Item -Force -Path "$libsDir/lib/crypto.lib" -Destination "$rootDir/crypto.lib"
   }
 }