diff --git a/docker/lib/dependabot/docker/requirement.rb b/docker/lib/dependabot/docker/requirement.rb
index 99fcbf5a1f2..0ad1abfd014 100644
--- a/docker/lib/dependabot/docker/requirement.rb
+++ b/docker/lib/dependabot/docker/requirement.rb
@@ -13,6 +13,10 @@ def self.requirements_array(requirement_string)
         [new(requirement_string)]
       end
 
+      def satisfied_by?(version)
+        super(version.release_part)
+      end
+
       # Patches Gem::Requirement to make it accept requirement strings like
       # "~> 4.2.5, >= 4.2.5.1" without first needing to split them.
       def initialize(*requirements)
diff --git a/docker/lib/dependabot/docker/version.rb b/docker/lib/dependabot/docker/version.rb
index 42d2b835eef..98bc8b6ac38 100644
--- a/docker/lib/dependabot/docker/version.rb
+++ b/docker/lib/dependabot/docker/version.rb
@@ -4,9 +4,28 @@
 
 module Dependabot
   module Docker
+    # In the special case of Java, the version string may also contain
+    # optional "update number" and "identifier" components.
+    # See https://www.oracle.com/java/technologies/javase/versioning-naming.html
+    # for a description of Java versions.
+    #
     class Version < Gem::Version
       def initialize(version)
-        super(version.tr("_", "."))
+        release_part, update_part = version.split("_", 2)
+
+        @release_part = Gem::Version.new(release_part)
+
+        @update_part = Gem::Version.new(update_part&.start_with?(/[0-9]/) ? update_part : 0)
+      end
+
+      attr_reader :release_part
+
+      def <=>(other)
+        sort_criteria <=> other.sort_criteria
+      end
+
+      def sort_criteria
+        [@release_part, @update_part]
       end
     end
   end
diff --git a/docker/spec/dependabot/docker/update_checker_spec.rb b/docker/spec/dependabot/docker/update_checker_spec.rb
index 0f298016935..b6558f1e4f6 100644
--- a/docker/spec/dependabot/docker/update_checker_spec.rb
+++ b/docker/spec/dependabot/docker/update_checker_spec.rb
@@ -413,7 +413,7 @@
       it { is_expected.to eq("jdk-11.0.2.9-alpine-slim") }
     end
 
-    context "when the dependencies have a underscore" do
+    context "when the dependencies have an underscore" do
       let(:dependency_name) { "eclipse-temurin" }
       let(:tags_fixture_name) { "eclipse-temurin.json" }
       let(:repo_url) do
@@ -448,6 +448,11 @@
         let(:version) { "17.0.1_12-jre-alpine" }
         it { is_expected.to eq("17.0.2_8-jre-alpine") }
       end
+
+      context "followed by numbers and with less components than other version but higher underscore part" do
+        let(:version) { "11.0.16_8-jdk" }
+        it { is_expected.to eq("11.0.16.1_1-jdk") }
+      end
     end
 
     context "when the dependency has a namespace" do
diff --git a/docker/spec/dependabot/docker/version_spec.rb b/docker/spec/dependabot/docker/version_spec.rb
new file mode 100644
index 00000000000..db938840991
--- /dev/null
+++ b/docker/spec/dependabot/docker/version_spec.rb
@@ -0,0 +1,18 @@
+# frozen_string_literal: true
+
+require "spec_helper"
+require "dependabot/docker/version"
+
+RSpec.describe Dependabot::Docker::Version do
+  describe ".new" do
+    it "sorts properly" do
+      expect(described_class.new("2.4.2")).to be >= described_class.new("2.1.0")
+      expect(described_class.new("2.4.2")).to be < described_class.new("2.4.3")
+    end
+
+    it "sorts properly when it uses underscores" do
+      expect(described_class.new("11.0.16_8-jdk")).to be < described_class.new("11.0.16.1-jdk")
+      expect(described_class.new("17.0.2_8-jdk")).to be > described_class.new("17.0.1_12-jdk")
+    end
+  end
+end
diff --git a/docker/spec/fixtures/docker/registry_tags/eclipse-temurin.json b/docker/spec/fixtures/docker/registry_tags/eclipse-temurin.json
index 07d197ec525..376e68b7968 100644
--- a/docker/spec/fixtures/docker/registry_tags/eclipse-temurin.json
+++ b/docker/spec/fixtures/docker/registry_tags/eclipse-temurin.json
@@ -6,6 +6,8 @@
         "17.0.1_12-jre-alpine",
         "17-jre-alpine",
         "11.0.14_9-jre-alpine",
-        "11-jre-alpine"
+        "11-jre-alpine",
+        "11.0.16_8-jdk",
+        "11.0.16.1_1-jdk"
     ]
 }