diff --git a/5.0/alpine3.19/Dockerfile b/5.0/alpine3.21/Dockerfile
similarity index 96%
rename from 5.0/alpine3.19/Dockerfile
rename to 5.0/alpine3.21/Dockerfile
index 76d3c54..800d15b 100644
--- a/5.0/alpine3.19/Dockerfile
+++ b/5.0/alpine3.21/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM ruby:3.1-alpine3.19
+FROM ruby:3.1-alpine3.21
 
 # explicitly set uid/gid to guarantee that it won't change in the future
 # the values 999:999 are identical to the current user/group id assigned
@@ -119,6 +119,9 @@ RUN set -eux; \
 		echo "$adapter:" >> ./config/database.yml; \
 		echo "  adapter: $adapter" >> ./config/database.yml; \
 	done; \
+	# Fix incompatibility with sqlite 1.4 in alpine 3.21
+	grep -q 'sqlite3", "~> 1.4.0"' Gemfile; \
+	sed -i -e 's/"sqlite3", "~> 1.4.0"/"sqlite3", "~> 1.5.0"/g' Gemfile; \
 	gosu redmine bundle install --jobs "$(nproc)"; \
 	rm ./config/database.yml; \
 # fix permissions for running as an arbitrary user
diff --git a/5.0/alpine3.19/docker-entrypoint.sh b/5.0/alpine3.21/docker-entrypoint.sh
similarity index 100%
rename from 5.0/alpine3.19/docker-entrypoint.sh
rename to 5.0/alpine3.21/docker-entrypoint.sh
diff --git a/5.1/alpine3.19/Dockerfile b/5.1/alpine3.21/Dockerfile
similarity index 99%
rename from 5.1/alpine3.19/Dockerfile
rename to 5.1/alpine3.21/Dockerfile
index 57f6566..535f7e8 100644
--- a/5.1/alpine3.19/Dockerfile
+++ b/5.1/alpine3.21/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM ruby:3.2-alpine3.19
+FROM ruby:3.2-alpine3.21
 
 # explicitly set uid/gid to guarantee that it won't change in the future
 # the values 999:999 are identical to the current user/group id assigned
diff --git a/5.1/alpine3.19/docker-entrypoint.sh b/5.1/alpine3.21/docker-entrypoint.sh
similarity index 100%
rename from 5.1/alpine3.19/docker-entrypoint.sh
rename to 5.1/alpine3.21/docker-entrypoint.sh
diff --git a/6.0/alpine3.19/Dockerfile b/6.0/alpine3.21/Dockerfile
similarity index 99%
rename from 6.0/alpine3.19/Dockerfile
rename to 6.0/alpine3.21/Dockerfile
index efcc905..876027c 100644
--- a/6.0/alpine3.19/Dockerfile
+++ b/6.0/alpine3.21/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM ruby:3.3-alpine3.19
+FROM ruby:3.3-alpine3.21
 
 # explicitly set uid/gid to guarantee that it won't change in the future
 # the values 999:999 are identical to the current user/group id assigned
diff --git a/6.0/alpine3.19/docker-entrypoint.sh b/6.0/alpine3.21/docker-entrypoint.sh
similarity index 100%
rename from 6.0/alpine3.19/docker-entrypoint.sh
rename to 6.0/alpine3.21/docker-entrypoint.sh
diff --git a/Dockerfile-alpine.template b/Dockerfile-alpine.template
index c368383..67c3b0d 100644
--- a/Dockerfile-alpine.template
+++ b/Dockerfile-alpine.template
@@ -115,6 +115,11 @@ RUN set -eux; \
 		echo "$adapter:" >> ./config/database.yml; \
 		echo "  adapter: $adapter" >> ./config/database.yml; \
 	done; \
+{{ if env.version == "5.0" and (env.variant | startswith("alpine")) and env.variant != "alpine3.20" then ( -}}
+	# Fix incompatibility with sqlite 1.4 in alpine 3.21
+	grep -q 'sqlite3", "~> 1.4.0"' Gemfile; \
+	sed -i -e 's/"sqlite3", "~> 1.4.0"/"sqlite3", "~> 1.5.0"/g' Gemfile; \
+{{ ) else "" end -}}
 	gosu redmine bundle install --jobs "$(nproc)"; \
 	rm ./config/database.yml; \
 # fix permissions for running as an arbitrary user
diff --git a/versions.json b/versions.json
index c9ec692..365c56d 100644
--- a/versions.json
+++ b/versions.json
@@ -1,6 +1,6 @@
 {
   "5.0": {
-    "alpine": "3.20",
+    "alpine": "3.21",
     "debian": "bookworm",
     "downloadUrl": "https://www.redmine.org/releases/redmine-5.0.10.tar.gz",
     "ruby": {
@@ -9,13 +9,13 @@
     "sha256": "cb0df0f6feb5a3198e59e36b239e9a1110011ed7078316bd1c8058247f5b9506",
     "variants": [
       "bookworm",
-      "alpine3.20",
-      "alpine3.19"
+      "alpine3.21",
+      "alpine3.20"
     ],
     "version": "5.0.10"
   },
   "5.1": {
-    "alpine": "3.20",
+    "alpine": "3.21",
     "debian": "bookworm",
     "downloadUrl": "https://www.redmine.org/releases/redmine-5.1.4.tar.gz",
     "ruby": {
@@ -24,13 +24,13 @@
     "sha256": "f5738d6a107f231b8f4b0ae5410e0c45742d75e0ef30c4b31a27c0ac9dafd51c",
     "variants": [
       "bookworm",
-      "alpine3.20",
-      "alpine3.19"
+      "alpine3.21",
+      "alpine3.20"
     ],
     "version": "5.1.4"
   },
   "6.0": {
-    "alpine": "3.20",
+    "alpine": "3.21",
     "debian": "bookworm",
     "downloadUrl": "https://www.redmine.org/releases/redmine-6.0.1.tar.gz",
     "ruby": {
@@ -39,8 +39,8 @@
     "sha256": "dcee3f15e3c15b9dbefba1fa9d8dfa12e89a7d40b3f3ed82da903d80d2548030",
     "variants": [
       "bookworm",
-      "alpine3.20",
-      "alpine3.19"
+      "alpine3.21",
+      "alpine3.20"
     ],
     "version": "6.0.1"
   }
diff --git a/versions.sh b/versions.sh
index d9896f7..7e032e4 100755
--- a/versions.sh
+++ b/versions.sh
@@ -5,8 +5,8 @@ supportedDebianSuites=(
 	bookworm
 )
 supportedAlpineVersions=(
+	3.21
 	3.20
-	3.19
 )
 
 defaultDebianSuite="${supportedDebianSuites[0]}"