diff --git a/.circleci/config.yml b/.circleci/config.yml
index 439620a02f1a..03ef7172f37e 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/1.4.1/crystal-1.4.1-1"
+    default: "https://github.com/crystal-lang/crystal/releases/download/1.5.0/crystal-1.5.0-1"
 
 defaults:
   environment: &env
diff --git a/.github/workflows/linux.yml b/.github/workflows/linux.yml
index 076ef4ddca0a..7c5e1f73319f 100644
--- a/.github/workflows/linux.yml
+++ b/.github/workflows/linux.yml
@@ -15,7 +15,7 @@ jobs:
     runs-on: ubuntu-latest
     strategy:
       matrix:
-        crystal_bootstrap_version: [1.2.2, 1.3.2, 1.4.1]
+        crystal_bootstrap_version: [1.2.2, 1.3.2, 1.4.1, 1.5.0]
         include:
           # libffi is only available starting from the 1.2.2 build images
           - crystal_bootstrap_version: 1.0.0
diff --git a/.github/workflows/openssl.yml b/.github/workflows/openssl.yml
index f240c62b3d9e..23a33a9f09f6 100644
--- a/.github/workflows/openssl.yml
+++ b/.github/workflows/openssl.yml
@@ -6,7 +6,7 @@ jobs:
   openssl3:
     runs-on: ubuntu-latest
     name: "OpenSSL 3.0"
-    container: crystallang/crystal:1.4.1-alpine
+    container: crystallang/crystal:1.5.0-alpine
     steps:
       - name: Download Crystal source
         uses: actions/checkout@v2
@@ -23,7 +23,7 @@ jobs:
   openssl111:
     runs-on: ubuntu-latest
     name: "OpenSSL 1.1.1"
-    container: crystallang/crystal:1.4.1-alpine
+    container: crystallang/crystal:1.5.0-alpine
     steps:
       - name: Download Crystal source
         uses: actions/checkout@v2
@@ -36,7 +36,7 @@ jobs:
   libressl31:
     runs-on: ubuntu-latest
     name: "LibreSSL 3.1"
-    container: crystallang/crystal:1.4.1-alpine
+    container: crystallang/crystal:1.5.0-alpine
     steps:
       - name: Download Crystal source
         uses: actions/checkout@v2
@@ -51,7 +51,7 @@ jobs:
   libressl34:
     runs-on: ubuntu-latest
     name: "LibreSSL 3.4"
-    container: crystallang/crystal:1.4.1-alpine
+    container: crystallang/crystal:1.5.0-alpine
     steps:
       - name: Download Crystal source
         uses: actions/checkout@v2
diff --git a/.github/workflows/win.yml b/.github/workflows/win.yml
index cddd199ab564..c2016ce612fa 100644
--- a/.github/workflows/win.yml
+++ b/.github/workflows/win.yml
@@ -5,7 +5,7 @@ on: [push, pull_request]
 jobs:
   x86_64-linux-job:
     runs-on: ubuntu-latest
-    container: crystallang/crystal:1.4.1-build
+    container: crystallang/crystal:1.5.0-build
     steps:
       - name: Download Crystal source
         uses: actions/checkout@v2
diff --git a/bin/ci b/bin/ci
index 8bf9cce968c7..f6ae8c562ba0 100755
--- a/bin/ci
+++ b/bin/ci
@@ -135,8 +135,8 @@ format() {
 prepare_build() {
   on_linux verify_linux_environment
 
-  on_osx curl -L https://github.com/crystal-lang/crystal/releases/download/1.4.1/crystal-1.4.1-1-darwin-universal.tar.gz -o ~/crystal.tar.gz
-  on_osx 'pushd ~;gunzip -c ~/crystal.tar.gz | tar xopf -;mv crystal-1.4.1-1 crystal;popd'
+  on_osx curl -L https://github.com/crystal-lang/crystal/releases/download/1.5.0/crystal-1.5.0-1-darwin-universal.tar.gz -o ~/crystal.tar.gz
+  on_osx 'pushd ~;gunzip -c ~/crystal.tar.gz | tar xopf -;mv crystal-1.5.0-1 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
@@ -189,7 +189,7 @@ with_build_env() {
 
   on_linux verify_linux_environment
 
-  export DOCKER_TEST_PREFIX="${DOCKER_TEST_PREFIX:=crystallang/crystal:1.4.1}"
+  export DOCKER_TEST_PREFIX="${DOCKER_TEST_PREFIX:=crystallang/crystal:1.5.0}"
 
   case $ARCH in
     x86_64)
diff --git a/shell.nix b/shell.nix
index becd04baab31..b03d3c7632d8 100644
--- a/shell.nix
+++ b/shell.nix
@@ -52,13 +52,13 @@ let
   # Hashes obtained using `nix-prefetch-url --unpack <url>`
   latestCrystalBinary = genericBinary ({
     x86_64-darwin = {
-      url = "https://github.com/crystal-lang/crystal/releases/download/1.4.1/crystal-1.4.1-1-darwin-universal.tar.gz";
-      sha256 = "sha256:0ckbsgr1y64w0yj80dn8v7zi6zqdlpin35l742rrblhzbdhdkalw";
+      url = "https://github.com/crystal-lang/crystal/releases/download/1.5.0/crystal-1.5.0-1-darwin-universal.tar.gz";
+      sha256 = "sha256:15h1qg4wa3zbp8p9vkvcqmy7ba1sc995r5z6d0yhx0h7nkgaw607";
     };
 
     x86_64-linux = {
-      url = "https://github.com/crystal-lang/crystal/releases/download/1.4.1/crystal-1.4.1-1-linux-x86_64.tar.gz";
-      sha256 = "sha256:1j5b2f4s2g8c1x7mhvsdzzjw878x0kkbrih4plxlzg3hmijvrnwj";
+      url = "https://github.com/crystal-lang/crystal/releases/download/1.5.0/crystal-1.5.0-1-linux-x86_64.tar.gz";
+      sha256 = "sha256:1xp1bbljwbff5zf585bz1cbkcb1whswl4fljakfxr7cbaw31jg9y";
     };
   }.${pkgs.stdenv.system});