diff --git a/pkgs/by-name/um/umple/2DShapes.ump b/pkgs/by-name/um/umple/2DShapes.ump
new file mode 100644
index 000000000000..427d794b44e5
--- /dev/null
+++ b/pkgs/by-name/um/umple/2DShapes.ump
@@ -0,0 +1,62 @@
+// Taken from https://github.com/umple/Umple/wiki/examples
+
+// 2D Shapes class hierarchy - sample UML class
+// diagram in Umple
+// From Book by Lethbridge and Laganiere, McGraw Hill 2004
+// Object-Oriented Software Engineering:
+//   Practical Software Engineering using UML and Java
+// See https://www.site.uottawa.ca/school/research/lloseng/
+
+//Namespace for core of the system.
+namespace Shapes.core;
+
+class Shape2D {
+ center;
+}
+//Abstract
+class EllipticalShape {
+ isA Shape2D;
+ semiMajorAxis;
+}
+//Abstract
+class Polygon {
+ isA Shape2D;
+}
+class Circle {
+ isA EllipticalShape;
+}
+class Ellipse{
+ isA EllipticalShape;
+}
+class SimplePolygon {
+ orientation;
+ isA Polygon;
+}
+class ArbitraryPolygon {
+ points;
+ isA Polygon;
+}
+class Rectangle {
+ isA SimplePolygon;
+ height;
+ width;
+}
+class RegularPolygon {
+ numPoints;
+ radius;
+ isA SimplePolygon;
+}
+
+class Shape2D {
+  public static void main(String [] argc) Java {
+    Shape2D s = new
+      RegularPolygon("0,0","0","3","100");
+    System.out.println(s);
+  }
+
+  public static void main(String [] argc) Python{
+    import RegularPolygon
+    s = RegularPolygon.RegularPolygon("0,0","0","3","100")
+    print(str(s))
+  }
+}
diff --git a/pkgs/by-name/um/umple/deps.json b/pkgs/by-name/um/umple/deps.json
new file mode 100644
index 000000000000..74ff05bdcd87
--- /dev/null
+++ b/pkgs/by-name/um/umple/deps.json
@@ -0,0 +1,622 @@
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+  },
+  "org/sonatype/sisu/inject#cglib/2.2.1-v20090111": {
+   "pom": "sha256-SvNVR7tds+Sft1CGWvDjM6/cgubm19itvRwUEd+tYIE="
+  }
+ },
+ "https://repository.jboss.org": {
+  "nexus/content/groups/public-jboss/com/google/guava/guava/maven-metadata": {
+   "xml": {
+    "groupId": "com.google.guava",
+    "lastUpdated": "20160429131712",
+    "release": "20.0-hal"
+   }
+  }
+ }
+}
diff --git a/pkgs/by-name/um/umple/fix-manpage.patch b/pkgs/by-name/um/umple/fix-manpage.patch
new file mode 100644
index 000000000000..19f01ec569ba
--- /dev/null
+++ b/pkgs/by-name/um/umple/fix-manpage.patch
@@ -0,0 +1,13 @@
+--- a/build.gradle
++++ b/build.gradle
+@@ -605,8 +605,8 @@ task packageAllJars {
+ 
+ // Generate options text from help message
+ task genOptions(type:Exec) {
+-  workingDir "${rootProject.projectDir.toString()}/dist/"
+-  commandLine 'java', '-jar', 'umple.jar', '-help'
++  workingDir "${rootProject.projectDir.toString()}/dist/gradle/libs/"
++  commandLine 'java', '-jar', '@UMPLE_OUT_JAR@', '-help'
+   standardOutput = new ByteArrayOutputStream()
+   doLast {
+     def strings = standardOutput.toString().split('-----------')
diff --git a/pkgs/by-name/um/umple/gradle-8-compat.patch b/pkgs/by-name/um/umple/gradle-8-compat.patch
new file mode 100644
index 000000000000..f05059be10ee
--- /dev/null
+++ b/pkgs/by-name/um/umple/gradle-8-compat.patch
@@ -0,0 +1,48 @@
+diff --git a/build.gradle b/build.gradle
+index 897ab9d0a..ff84824f9 100644
+--- a/build.gradle
++++ b/build.gradle
+@@ -10,7 +10,7 @@ buildscript {
+ }
+ 
+ plugins {
+-  id 'nebula.ospackage' version '9.1.1'
++  id 'com.netflix.nebula.ospackage' version '12.3.0'
+ }
+ 
+ String runGit(List<String> args, String fallback) {
+@@ -376,7 +376,6 @@ sourceSets {
+             ]
+             exclude '**/*.ump', '**/.git*'
+         }
+-        java.outputDir = file(rootProject.ext.classfileOutputDir)
+     }
+     test {
+         compileClasspath = files(
+@@ -394,10 +393,16 @@ sourceSets {
+             ]
+             exclude '**/*.ump', '**/.git*'
+         }
+-        java.outputDir = file(rootProject.ext.testClassfileOutputDir)
+     }
+ }
+ 
++tasks.named("compileJava") {
++    destinationDirectory.set(file(rootProject.ext.classfileOutputDir))
++}
++
++tasks.named("compileTestJava") {
++    destinationDirectory.set(file(rootProject.ext.testClassfileOutputDir))
++}
+ 
+ // ===============
+ //  Jar packaging
+@@ -2011,7 +2016,7 @@ task executeDocJar (type: JavaExec){
+     def drop = fileTree ("${rootProject.ext.umpleoscripts}/dropbox") {
+       include '*.js'
+     }
+-   files = files (
++   files = project.files (
+      'umpleonline/scripts/prototype.js',
+      'umpleonline/scripts/dom.js',
+      'umpleonline/scripts/ajax.js', 
diff --git a/pkgs/by-name/um/umple/package.nix b/pkgs/by-name/um/umple/package.nix
new file mode 100644
index 000000000000..d3234708baa2
--- /dev/null
+++ b/pkgs/by-name/um/umple/package.nix
@@ -0,0 +1,159 @@
+{
+  lib,
+  stdenvNoCC,
+  runCommand,
+  fetchurl,
+  fetchFromGitHub,
+  gradle_8, # incompatible with gradle 9+
+  installShellFiles,
+  makeBinaryWrapper,
+  opentxl,
+  jre,
+}:
+let
+  versions = lib.importJSON ./versions.json;
+  inherit (versions.umple) version longVersion;
+
+  # Required for bootstrapping
+  umpleJar = fetchurl versions.umpleJar;
+
+  # Not managed through Gradle
+  joptSimple = fetchFromGitHub {
+    owner = "jopt-simple";
+    repo = "jopt-simple";
+    tag = "jopt-simple-4.4";
+    hash = "sha256-sOQaEq2qzvEwJzwZIcMQus3tetzA6O2VPl8XUJAtupM=";
+  };
+
+in
+stdenvNoCC.mkDerivation (finalAttrs: {
+  pname = "umple";
+  inherit version;
+
+  src = fetchFromGitHub {
+    owner = "umple";
+    repo = "umple";
+    tag = "v${version}";
+    hash = "sha256-BPy1L3bzvKoywM0srv36SXVe8psaY/m0bljy30z5dr8=";
+  };
+
+  patches = [
+    # The upstream project uses some deprecated Gradle 7 features and old dependencies
+    ./gradle-8-compat.patch
+    # Replaces the logic to determine the current version (requires Git at runtime)
+    ./replace-version.patch
+    # Fixes broken working directory + updates Jar paths for manpage generation task
+    ./fix-manpage.patch
+  ];
+
+  strictDeps = true;
+  __structuredAttrs = true;
+
+  nativeBuildInputs = [
+    gradle_8
+    gradle_8.jdk
+    installShellFiles
+    makeBinaryWrapper
+    opentxl
+  ];
+
+  postPatch = ''
+    # Set variables from patches + use Nix store paths
+    substituteInPlace build.gradle \
+      --replace-fail @UMPLE_VERSION@ "${longVersion}" \
+      --replace-fail @UMPLE_OUT_JAR@ "umple-${longVersion}.jar" \
+      --replace-fail '${"$"}{rootProject.projectDir.toString()}/libs/umple-latest.jar' '${umpleJar}' \
+      --replace-fail '${"$"}{rootProject.projectDir.toString()}/dist/gradle/libs/vendors/jopt-simple-jopt-simple-4.4/src/main/java/joptsimple' '${joptSimple}/src/main/java/joptsimple'
+
+    # Replace outdated version in manpage
+    substituteInPlace build/package-files/template.1 \
+      --replace-warn 1.31.1 "${longVersion}"
+
+    # Replace @UMPLE_VERSION@ template in original source code with actual version.
+    # This ensures that emitted files include comments indicating the proper version,
+    # e.g. "Generated with Umple x.y.z"
+    find . -type f \( -name '*.java' -o -name '*.ump' \) -exec sed -i "s/@UMPLE_VERSION@/${longVersion}/g" {} +
+  '';
+
+  mitmCache = gradle_8.fetchDeps {
+    inherit (finalAttrs) pname;
+    data = ./deps.json;
+  };
+
+  __darwinAllowLocalNetworking = true;
+
+  gradleBuildTask = "quickbuild";
+
+  gradleFlags = [
+    # Network-dependent tasks
+    "--exclude-task=downloadUmpleJar"
+    "--exclude-task=downloadJOptSimpleVendorZip"
+    "--exclude-task=downloadAndUnzipJOptSimpleVendor"
+    "--exclude-task=prepareJOptSimpleVendor"
+    # Tasks that try to modify readonly files
+    "--exclude-task=cleanUpUmple"
+  ];
+
+  postBuild = ''
+    gradle --no-daemon genManpage
+  '';
+
+  installPhase = ''
+    runHook preInstall
+
+    mkdir -p $out/{bin,share/java}
+    cp dist/gradle/libs/umple*.jar $out/share/java
+    installManPage build/package-files/umple.1
+
+    pushd $out/share/java
+    # Strip version suffix from filenames
+    for file in *.jar; do
+      mv "$file" "''${file%-${longVersion}.jar}.jar"
+    done
+    # Create wrappers
+    for file in *.jar; do
+      makeWrapper ${lib.getExe jre} "$out/bin/''${file%.jar}" \
+        --add-flags "-jar $out/share/java/$file"
+    done
+    popd
+
+    runHook postInstall
+  '';
+
+  passthru = {
+    updateScript = ./update.sh;
+
+    bootstrap = umpleJar;
+
+    tests."2dshapes" =
+      runCommand "umple-test"
+        {
+          nativeBuildInputs = [
+            finalAttrs.finalPackage
+            gradle_8.jdk
+          ];
+          src = ./2DShapes.ump;
+        }
+        ''
+          set -euo pipefail
+          cp $src .
+          umple $(basename $src)
+          javac -d bin Shapes/core/*.java
+          java -cp bin Shapes.core.Shape2D
+          touch $out
+        '';
+  };
+
+  meta = {
+    description = "Model-oriented programming language and modelling tool for integrating UML constructs into high-level languages";
+    mainProgram = "umple";
+    homepage = "https://github.com/umple/umple";
+    downloadPage = "https://github.com/umple/umple/releases";
+    license = lib.licenses.mit;
+    sourceProvenance = with lib.sourceTypes; [
+      fromSource
+      binaryBytecode
+    ];
+    maintainers = with lib.maintainers; [ MysteryBlokHed ];
+  };
+})
diff --git a/pkgs/by-name/um/umple/replace-version.patch b/pkgs/by-name/um/umple/replace-version.patch
new file mode 100644
index 000000000000..f376b15c2ec8
--- /dev/null
+++ b/pkgs/by-name/um/umple/replace-version.patch
@@ -0,0 +1,11 @@
+--- a/build.gradle
++++ b/build.gradle
+@@ -32,7 +32,7 @@ ext {
+     umpleMajorVersionFile = new File("${rootProject.projectDir.toString()}/build/umpleversion.txt")
+     umpleLastVersion = new org.yaml.snakeyaml.Yaml().load(rootProject.ext.umpleLastVersionFile.newInputStream()).version
+     umpleMajorVersion = new org.yaml.snakeyaml.Yaml().load(rootProject.ext.umpleMajorVersionFile.newInputStream()).version
+-    umpleCurrentVersion = "${rootProject.ext.umpleMajorVersion}.${runGit(['rev-list', '--count', 'master'], 'x')}.${runGit(['rev-parse', '--short', 'master'], 'dev')}"
++    umpleCurrentVersion = "@UMPLE_VERSION@"
+     umpleCurrentJarBase = "umple-${rootProject.ext.umpleCurrentVersion}"
+     umpleCurrentJar = "${rootProject.projectDir.toString()}/dist/gradle/libs/${rootProject.ext.umpleCurrentJarBase}.jar"
+     umpleJarRemoteSource = "https://cruise.umple.org/umpleonline/scripts/umple.jar"
diff --git a/pkgs/by-name/um/umple/update.sh b/pkgs/by-name/um/umple/update.sh
new file mode 100755
index 000000000000..0ec6f3e14525
--- /dev/null
+++ b/pkgs/by-name/um/umple/update.sh
@@ -0,0 +1,67 @@
+#!/usr/bin/env nix-shell
+#!nix-shell -i bash -p curl git jq nix-update
+set -euo pipefail
+
+release=$(curl -s ${GITHUB_TOKEN:+" -u \":$GITHUB_TOKEN\""} https://api.github.com/repos/umple/umple/releases/latest)
+latestTag=$(echo "$release" | jq -r '.tag_name')
+latestVersion="${latestTag#v}"
+currentVersion=$(nix-instantiate --eval -E "with import ./. {}; umple.version or (lib.getVersion umple)" | tr -d '"')
+echo "Current version: $currentVersion"
+echo "Latest version: $latestVersion"
+
+if [[ "$currentVersion" = "$latestVersion" ]]; then
+  echo "Up-to-date."
+  exit
+fi
+
+echo "Updating to $latestVersion"
+
+location="$(dirname -- "${BASH_SOURCE[0]}")"
+
+# Get commit count and hash from upstream repository tag
+tmpdir=$(mktemp -d)
+trap 'rm -rf "$tmpdir"' EXIT
+
+pushd "$tmpdir"
+git clone --branch "$latestVersion" --single-branch https://github.com/umple/umple.git .
+revision=$(git rev-parse --short HEAD)
+commitCount=$(git rev-list --count HEAD)
+longVersion="$latestVersion.$commitCount.$revision"
+popd
+
+# Find the filename and hash of the latest stable Umple JAR for bootstrapping.
+# The best way to do this is to just check the prefix of release assets,
+# since the commit count + hash used don't match the release tag, for some reason.
+umpleName=$(echo "$release" | jq -r 'first(.assets[] | select(.name | startswith("umple-")) | .name)')
+if [[ -z "$umpleName" ]]; then
+  echo "Could not find Umple JAR in GitHub release assets."
+  exit 1
+fi
+
+umpleUrl="https://github.com/umple/umple/releases/download/$latestTag/$umpleName"
+umpleHash=$(nix --extra-experimental-features nix-command hash convert --hash-algo sha256 \
+  "$(nix-prefetch-url "$umpleUrl")")
+
+# Save version info
+jq -n \
+  --arg version "$latestVersion" \
+  --arg longVersion "$longVersion" \
+  --arg revision "$revision" \
+  --arg commitCount "$commitCount" \
+  --arg umpleUrl "$umpleUrl" \
+  --arg umpleHash "$umpleHash" \
+  '{
+    "umple": {
+      "version": $version,
+      "longVersion": $longVersion,
+      "revision": $revision,
+      "commitCount": $commitCount
+    },
+    "umpleJar": {
+      "url": $umpleUrl,
+      "hash": $umpleHash
+    }
+  }' > "$location/versions.json"
+
+# Version update is done; use nix-update for hashes and Gradle deps
+nix-update umple --version=skip
diff --git a/pkgs/by-name/um/umple/versions.json b/pkgs/by-name/um/umple/versions.json
new file mode 100644
index 000000000000..9ca7502961c5
--- /dev/null
+++ b/pkgs/by-name/um/umple/versions.json
@@ -0,0 +1,12 @@
+{
+  "umple": {
+    "version": "1.37.0",
+    "longVersion": "1.37.0.8543.1593c2b83",
+    "revision": "1593c2b83",
+    "commitCount": "8543"
+  },
+  "umpleJar": {
+    "url": "https://github.com/umple/umple/releases/download/v1.37.0/umple-1.37.0.8542.3a8c87689.jar",
+    "hash": "sha256-pBHHbURbe7B5A11tShvHGlSO4XMJPcdM7Iy+ph3PxAE="
+  }
+}