diff --git a/.circleci/config.yml b/.circleci/config.yml
index 28691e8b9a78..c672cad87847 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -8,7 +8,7 @@ parameters:
   previous_crystal_base_url:
     description: "Prefix for URLs to Crystal bootstrap compiler"
     type: string
-    default: "https://github.com/crystal-lang/crystal/releases/download/1.7.3/crystal-1.7.3-1"
+    default: "https://github.com/crystal-lang/crystal/releases/download/1.8.0/crystal-1.8.0-1"
 
 defaults:
   environment: &env
diff --git a/.github/workflows/interpreter.yml b/.github/workflows/interpreter.yml
index 1abb3cb16233..45eace56968f 100644
--- a/.github/workflows/interpreter.yml
+++ b/.github/workflows/interpreter.yml
@@ -13,7 +13,7 @@ jobs:
   test-interpreter_spec:
     runs-on: ubuntu-22.04
     container:
-      image: crystallang/crystal:1.7.3-build
+      image: crystallang/crystal:1.8.0-build
     name: "Test Interpreter"
     steps:
       - uses: actions/checkout@v3
@@ -24,7 +24,7 @@ jobs:
   build-interpreter:
     runs-on: ubuntu-22.04
     container:
-      image: crystallang/crystal:1.7.3-build
+      image: crystallang/crystal:1.8.0-build
     name: Build interpreter
     steps:
       - uses: actions/checkout@v3
@@ -43,7 +43,7 @@ jobs:
     needs: build-interpreter
     runs-on: ubuntu-22.04
     container:
-      image: crystallang/crystal:1.7.3-build
+      image: crystallang/crystal:1.8.0-build
     strategy:
       matrix:
         part: [0, 1, 2, 3]
diff --git a/.github/workflows/linux.yml b/.github/workflows/linux.yml
index 4f1344880c8c..3070efd70171 100644
--- a/.github/workflows/linux.yml
+++ b/.github/workflows/linux.yml
@@ -29,6 +29,8 @@ jobs:
             flags: "FLAGS=-Dwithout_ffi USE_PCRE1=true"
           - crystal_bootstrap_version: 1.7.3
             flags: ""
+          - crystal_bootstrap_version: 1.8.0
+            flags: ""
     steps:
       - name: Download Crystal source
         uses: actions/checkout@v3
diff --git a/.github/workflows/llvm.yml b/.github/workflows/llvm.yml
index d6f59d3f83e4..2b86b41542b0 100644
--- a/.github/workflows/llvm.yml
+++ b/.github/workflows/llvm.yml
@@ -43,7 +43,7 @@ jobs:
       - name: Install Crystal
         uses: crystal-lang/install-crystal@v1
         with:
-          crystal: "1.7.3"
+          crystal: "1.8.0"
 
       - name: Build libllvm_ext
         run: make -B deps
diff --git a/.github/workflows/openssl.yml b/.github/workflows/openssl.yml
index 52df94eb93a0..c572dafae072 100644
--- a/.github/workflows/openssl.yml
+++ b/.github/workflows/openssl.yml
@@ -10,7 +10,7 @@ jobs:
   openssl3:
     runs-on: ubuntu-latest
     name: "OpenSSL 3.0"
-    container: crystallang/crystal:1.7.3-alpine
+    container: crystallang/crystal:1.8.0-alpine
     steps:
       - name: Download Crystal source
         uses: actions/checkout@v3
@@ -19,7 +19,7 @@ jobs:
       - name: Upgrade alpine-keys
         run: apk upgrade alpine-keys
       - name: Install openssl 3.0
-        run: apk add "openssl3-dev" --repository=http://dl-cdn.alpinelinux.org/alpine/v3.15/main
+        run: apk add "openssl-dev=~3.0"
       - name: Check LibSSL version
         run: bin/crystal eval 'require "openssl"; p! LibSSL::OPENSSL_VERSION, LibSSL::LIBRESSL_VERSION'
       - name: Run OpenSSL specs
@@ -27,12 +27,14 @@ jobs:
   openssl111:
     runs-on: ubuntu-latest
     name: "OpenSSL 1.1.1"
-    container: crystallang/crystal:1.7.3-alpine
+    container: crystallang/crystal:1.8.0-alpine
     steps:
       - name: Download Crystal source
         uses: actions/checkout@v3
+      - name: Uninstall openssl
+        run: apk del openssl-dev
       - name: Install openssl 1.1.1
-        run: apk add "openssl-dev=~1.1.1"
+        run: apk add "openssl1.1-compat-dev=~1.1.1"
       - name: Check LibSSL version
         run: bin/crystal eval 'require "openssl"; p! LibSSL::OPENSSL_VERSION, LibSSL::LIBRESSL_VERSION'
       - name: Run OpenSSL specs
@@ -40,7 +42,7 @@ jobs:
   libressl34:
     runs-on: ubuntu-latest
     name: "LibreSSL 3.4"
-    container: crystallang/crystal:1.7.3-alpine
+    container: crystallang/crystal:1.8.0-alpine
     steps:
       - name: Download Crystal source
         uses: actions/checkout@v3
@@ -50,9 +52,6 @@ jobs:
         run: apk upgrade alpine-keys
       - name: Install libressl 3.4
         run: apk add "libressl-dev=~3.4" --repository=http://dl-cdn.alpinelinux.org/alpine/v3.15/community
-      # We need a recent libc which include reallocarray
-      - name: Upgrade musl-dev
-        run: apk add "musl-dev=~1.2" --repository=http://dl-cdn.alpinelinux.org/alpine/v3.15/main
       - name: Check LibSSL version
         run: bin/crystal eval 'require "openssl"; p! LibSSL::OPENSSL_VERSION, LibSSL::LIBRESSL_VERSION'
       - name: Run OpenSSL specs
diff --git a/.github/workflows/regex-engine.yml b/.github/workflows/regex-engine.yml
index 34bab7108845..e32c8e67f6d6 100644
--- a/.github/workflows/regex-engine.yml
+++ b/.github/workflows/regex-engine.yml
@@ -10,10 +10,12 @@ jobs:
   pcre:
     runs-on: ubuntu-latest
     name: "PCRE"
-    container: crystallang/crystal:1.7.3-alpine
+    container: crystallang/crystal:1.8.0-alpine
     steps:
       - name: Download Crystal source
         uses: actions/checkout@v3
+      - name: Remove PCRE2
+        run: apk del pcre2-dev
       - name: Assert using PCRE
         run: bin/crystal eval 'abort unless Regex::Engine == Regex::PCRE'
       - name: Run Regex specs
@@ -21,12 +23,10 @@ jobs:
   pcre2:
     runs-on: ubuntu-latest
     name: "PCRE2"
-    container: crystallang/crystal:1.7.3-alpine
+    container: crystallang/crystal:1.8.0-alpine
     steps:
       - name: Download Crystal source
         uses: actions/checkout@v3
-      - name: Install PCRE2
-        run: apk add pcre2-dev
       - name: Assert using PCRE2
         run: bin/crystal eval 'abort unless Regex::Engine == Regex::PCRE2'
       - name: Assert select PCRE
diff --git a/.github/workflows/wasm32.yml b/.github/workflows/wasm32.yml
index eb603f8f746c..db451ef6933e 100644
--- a/.github/workflows/wasm32.yml
+++ b/.github/workflows/wasm32.yml
@@ -12,7 +12,7 @@ env:
 jobs:
   wasm32-test:
     runs-on: ubuntu-latest
-    container: crystallang/crystal:1.7.3-build
+    container: crystallang/crystal:1.8.0-build
     steps:
       - name: Download Crystal source
         uses: actions/checkout@v3
diff --git a/.github/workflows/win.yml b/.github/workflows/win.yml
index 82436c50e992..344b0af94d0d 100644
--- a/.github/workflows/win.yml
+++ b/.github/workflows/win.yml
@@ -19,7 +19,7 @@ jobs:
       - name: Install Crystal
         uses: crystal-lang/install-crystal@v1
         with:
-          crystal: "1.7.3"
+          crystal: "1.8.0"
 
       - name: Download Crystal source
         uses: actions/checkout@v3
diff --git a/bin/ci b/bin/ci
index f416e3751bf1..b734c2e4c04f 100755
--- a/bin/ci
+++ b/bin/ci
@@ -134,8 +134,8 @@ format() {
 prepare_build() {
   on_linux verify_linux_environment
 
-  on_osx curl -L https://github.com/crystal-lang/crystal/releases/download/1.7.3/crystal-1.7.3-1-darwin-universal.tar.gz -o ~/crystal.tar.gz
-  on_osx 'pushd ~;gunzip -c ~/crystal.tar.gz | tar xopf -;mv crystal-1.7.3-1 crystal;popd'
+  on_osx curl -L https://github.com/crystal-lang/crystal/releases/download/1.8.0/crystal-1.8.0-1-darwin-universal.tar.gz -o ~/crystal.tar.gz
+  on_osx 'pushd ~;gunzip -c ~/crystal.tar.gz | tar xopf -;mv crystal-1.8.0-1 crystal;popd'
 
   # These commands may take a few minutes to run due to the large size of the repositories.
   # This restriction has been made on GitHub's request because updating shallow
@@ -188,7 +188,7 @@ with_build_env() {
 
   on_linux verify_linux_environment
 
-  export DOCKER_TEST_PREFIX="${DOCKER_TEST_PREFIX:=crystallang/crystal:1.7.3}"
+  export DOCKER_TEST_PREFIX="${DOCKER_TEST_PREFIX:=crystallang/crystal:1.8.0}"
 
   case $ARCH in
     x86_64)
diff --git a/shell.nix b/shell.nix
index 27c64ea7af8e..3b844ba588bc 100644
--- a/shell.nix
+++ b/shell.nix
@@ -52,18 +52,18 @@ let
   # Hashes obtained using `nix-prefetch-url --unpack <url>`
   latestCrystalBinary = genericBinary ({
     x86_64-darwin = {
-      url = "https://github.com/crystal-lang/crystal/releases/download/1.7.3/crystal-1.7.3-1-darwin-universal.tar.gz";
-      sha256 = "sha256:1jc3fdc36mpvh7zahszbij02c0nxhmmbpfjcpd890bapj2q4jkkr";
+      url = "https://github.com/crystal-lang/crystal/releases/download/1.8.0/crystal-1.8.0-1-darwin-universal.tar.gz";
+      sha256 = "sha256:1rwcx9bxxhfyw6zqd14drrqzhk72932zv2jgbrzrpyfmk2i63gng";
     };
 
     aarch64-darwin = {
-      url = "https://github.com/crystal-lang/crystal/releases/download/1.7.3/crystal-1.7.3-1-darwin-universal.tar.gz";
-      sha256 = "sha256:1jc3fdc36mpvh7zahszbij02c0nxhmmbpfjcpd890bapj2q4jkkr";
+      url = "https://github.com/crystal-lang/crystal/releases/download/1.8.0/crystal-1.8.0-1-darwin-universal.tar.gz";
+      sha256 = "sha256:1rwcx9bxxhfyw6zqd14drrqzhk72932zv2jgbrzrpyfmk2i63gng";
     };
 
     x86_64-linux = {
-      url = "https://github.com/crystal-lang/crystal/releases/download/1.7.3/crystal-1.7.3-1-linux-x86_64.tar.gz";
-      sha256 = "sha256:0diq6i760yd0rv310f80v60m015f5xkni7h60phspvmyy0yw9jv0";
+      url = "https://github.com/crystal-lang/crystal/releases/download/1.8.0/crystal-1.8.0-1-linux-x86_64.tar.gz";
+      sha256 = "sha256:0bnzbqil7avndz7qyijzixy4jsp3lk8dvyh6j7qarvjmrz5lj7m9";
     };
   }.${pkgs.stdenv.system});
 
diff --git a/src/VERSION b/src/VERSION
index 27f9cd322bb9..b57588e592f8 100644
--- a/src/VERSION
+++ b/src/VERSION
@@ -1 +1 @@
-1.8.0
+1.9.0-dev