diff --git a/5.0/alpine3.21/Dockerfile b/5.0/alpine3.21/Dockerfile
index 506f5dc..800d15b 100644
--- a/5.0/alpine3.21/Dockerfile
+++ b/5.0/alpine3.21/Dockerfile
@@ -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/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