diff --git a/pom.xml b/pom.xml
index 980c753b..1d3a79ac 100644
--- a/pom.xml
+++ b/pom.xml
@@ -126,6 +126,16 @@
                             <classpathScope>runtime</classpathScope>
                         </configuration>
                     </execution>
+                    <execution>
+                        <id>reset-db</id>
+                        <goals>
+                            <goal>java</goal>
+                        </goals>
+                        <configuration>
+                            <mainClass>com.petshop.backend.ResetDatabaseApplication</mainClass>
+                            <classpathScope>runtime</classpathScope>
+                        </configuration>
+                    </execution>
                     <execution>
                         <id>docker-up</id>
                         <goals>
diff --git a/src/main/java/com/petshop/backend/DevStackApplication.java b/src/main/java/com/petshop/backend/DevStackApplication.java
index 76b76de4..f60e9957 100644
--- a/src/main/java/com/petshop/backend/DevStackApplication.java
+++ b/src/main/java/com/petshop/backend/DevStackApplication.java
@@ -2,17 +2,12 @@ package com.petshop.backend;
 
 import com.petshop.backend.config.FlywayContextInitializer;
 import org.springframework.boot.builder.SpringApplicationBuilder;
+import org.springframework.boot.web.server.PortInUseException;
 import org.springframework.context.ConfigurableApplicationContext;
 import org.springframework.context.event.ContextClosedEvent;
 
-import java.io.BufferedReader;
-import java.io.IOException;
-import java.io.InputStreamReader;
-import java.nio.file.Path;
-import java.nio.file.Paths;
+import java.net.BindException;
 import java.time.Duration;
-import java.util.ArrayList;
-import java.util.List;
 import java.util.Locale;
 import java.util.concurrent.CountDownLatch;
 import java.util.concurrent.Executors;
@@ -25,133 +20,147 @@ public class DevStackApplication {
     private static final Duration WATCH_INTERVAL = Duration.ofSeconds(2);
 
     public static void main(String[] args) {
-        DevStackController controller = new DevStackController();
+        DockerComposeSupport docker = new DockerComposeSupport();
         ConfigurableApplicationContext context = null;
         CountDownLatch shutdownLatch = new CountDownLatch(1);
+        ScheduledExecutorService scheduler = null;
+        AtomicBoolean shuttingDown = new AtomicBoolean(false);
 
         try {
-            controller.startDatabase();
+            validateJavaVersion();
+            docker.ensureDockerAvailable();
+            docker.startDatabase();
             context = new SpringApplicationBuilder(BackendApplication.class)
                     .initializers(new FlywayContextInitializer())
                     .run(args);
-            ConfigurableApplicationContext appContext = context;
             context.addApplicationListener(event -> {
                 if (event instanceof ContextClosedEvent) {
                     shutdownLatch.countDown();
                 }
             });
-            controller.watchDatabase(appContext);
+            scheduler = startDatabaseWatch(docker, context, shuttingDown);
             shutdownLatch.await();
+        } catch (RuntimeException ex) {
+            throw new IllegalStateException(describeStartupFailure(ex), ex);
         } catch (InterruptedException ex) {
             Thread.currentThread().interrupt();
             throw new IllegalStateException("Dev stack interrupted", ex);
         } finally {
-            controller.stopWatching();
+            if (scheduler != null) {
+                scheduler.shutdownNow();
+            }
             if (context != null && context.isActive()) {
                 context.close();
             }
-            controller.stopDatabase();
+            if (!shuttingDown.get()) {
+                docker.stopDatabase();
+            }
         }
     }
 
-    private static final class DevStackController {
-        private final Path projectDir = Paths.get("").toAbsolutePath();
-        private final AtomicBoolean shuttingDown = new AtomicBoolean(false);
-        private ScheduledExecutorService scheduler;
-
-        private void startDatabase() {
-            runCommand(composeCommand("up", "-d", "--wait", "db"));
+    private static void validateJavaVersion() {
+        int feature = Runtime.version().feature();
+        if (feature < 25) {
+            throw new IllegalStateException("JDK 25 or newer is required. IntelliJ is currently using Java " + Runtime.version() + ".");
         }
+    }
 
-        private void stopDatabase() {
-            if (!shuttingDown.compareAndSet(false, true)) {
+    private static ScheduledExecutorService startDatabaseWatch(DockerComposeSupport docker, ConfigurableApplicationContext context, AtomicBoolean shuttingDown) {
+        ScheduledExecutorService scheduler = Executors.newSingleThreadScheduledExecutor();
+        scheduler.scheduleWithFixedDelay(() -> {
+            if (shuttingDown.get()) {
                 return;
             }
-            stopWatching();
-            runCommand(composeCommand("stop", "db"));
-        }
-
-        private void watchDatabase(ConfigurableApplicationContext context) {
-            scheduler = Executors.newSingleThreadScheduledExecutor();
-            scheduler.scheduleWithFixedDelay(() -> {
-                if (shuttingDown.get()) {
-                    return;
+            if (!docker.isDatabaseRunning()) {
+                shuttingDown.set(true);
+                if (context.isActive()) {
+                    context.close();
                 }
-                if (!isDatabaseRunning()) {
-                    shuttingDown.set(true);
-                    if (context.isActive()) {
-                        context.close();
-                    }
+            }
+        }, WATCH_INTERVAL.toSeconds(), WATCH_INTERVAL.toSeconds(), TimeUnit.SECONDS);
+        return scheduler;
+    }
+
+    private static String describeStartupFailure(RuntimeException ex) {
+        Throwable cause = deepestCause(ex);
+        String message = cause.getMessage();
+        String lowerMessage = "";
+        if (message != null) {
+            lowerMessage = message.toLowerCase(Locale.ROOT);
+        }
+
+        switch (classifyStartupFailure(cause, lowerMessage)) {
+            case SERVER_PORT_IN_USE:
+                return "Backend startup failed because port 8080 is already in use. Stop the other process or set SERVER_PORT to a different value.";
+            case DOCKER_NOT_RUNNING:
+                return "Backend startup failed because Docker is not available. Start Docker Desktop and try again.";
+            case DOCKER_NOT_INSTALLED:
+                return "Backend startup failed because Docker is not installed or not on PATH. Install Docker Desktop and reopen IntelliJ.";
+            case DATABASE_PORT_IN_USE:
+                return "Backend startup failed because port 3306 is already in use. Stop the conflicting MySQL service or container, then run Reset Database and try again.";
+            case STALE_SCHEMA:
+                return "Backend startup failed because the database schema is stale or incomplete. Run Reset Database and then start Pet Shop Application again.";
+            case FLYWAY_MIGRATION_FAILED:
+                return "Backend startup failed during Flyway migration. Run Reset Database and check the database logs if the problem persists.";
+            case DATASOURCE_CONFIG_MISSING:
+                return "Backend startup failed because datasource configuration was not loaded. Reload the Maven project and rerun Pet Shop Application.";
+            case DATABASE_UNREACHABLE:
+                return "Backend startup failed because it could not connect to MySQL. Make sure Docker Desktop is running, the database container is healthy, and port 3306 is reachable.";
+            case UNKNOWN:
+                if (message == null || message.isBlank()) {
+                    return "Backend startup failed: " + ex.getClass().getSimpleName();
                 }
-            }, WATCH_INTERVAL.toSeconds(), WATCH_INTERVAL.toSeconds(), TimeUnit.SECONDS);
-        }
-
-        private void stopWatching() {
-            if (scheduler != null) {
-                scheduler.shutdownNow();
-                scheduler = null;
-            }
-        }
-
-        private boolean isDatabaseRunning() {
-            CommandResult result = runCommand(composeCommand("ps", "--status", "running", "--services", "db"), false);
-            return result.exitCode == 0 && result.output.lines()
-                    .map(String::trim)
-                    .anyMatch("db"::equals);
-        }
-
-        private List<String> composeCommand(String... args) {
-            List<String> command = new ArrayList<>();
-            command.add(resolveDockerExecutable());
-            command.add("compose");
-            command.add("-f");
-            command.add("docker-compose.dev.yml");
-            for (String arg : args) {
-                command.add(arg);
-            }
-            return command;
-        }
-
-        private String resolveDockerExecutable() {
-            String os = System.getProperty("os.name", "").toLowerCase(Locale.ROOT);
-            return os.contains("win") ? "docker.exe" : "docker";
-        }
-
-        private void runCommand(List<String> command) {
-            CommandResult result = runCommand(command, true);
-            if (result.exitCode != 0) {
-                throw new IllegalStateException(result.output.isBlank() ? "Command failed: " + String.join(" ", command) : result.output);
-            }
-        }
-
-        private CommandResult runCommand(List<String> command, boolean printOutput) {
-            ProcessBuilder builder = new ProcessBuilder(command);
-            builder.directory(projectDir.toFile());
-            builder.redirectErrorStream(true);
-
-            try {
-                Process process = builder.start();
-                StringBuilder output = new StringBuilder();
-                try (BufferedReader reader = new BufferedReader(new InputStreamReader(process.getInputStream()))) {
-                    String line;
-                    while ((line = reader.readLine()) != null) {
-                        output.append(line).append(System.lineSeparator());
-                        if (printOutput) {
-                            System.out.println(line);
-                        }
-                    }
-                }
-                int exitCode = process.waitFor();
-                return new CommandResult(exitCode, output.toString().trim());
-            } catch (IOException ex) {
-                throw new IllegalStateException("Unable to run docker command", ex);
-            } catch (InterruptedException ex) {
-                Thread.currentThread().interrupt();
-                throw new IllegalStateException("Docker command interrupted", ex);
-            }
+                return "Backend startup failed: " + message;
+            default:
+                throw new IllegalStateException("Unhandled startup failure classification");
         }
     }
 
-    private record CommandResult(int exitCode, String output) {
+    private static StartupFailure classifyStartupFailure(Throwable cause, String lowerMessage) {
+        if (cause instanceof PortInUseException || cause instanceof BindException || lowerMessage.contains("port 8080") && lowerMessage.contains("already in use")) {
+            return StartupFailure.SERVER_PORT_IN_USE;
+        }
+        if (lowerMessage.contains("docker desktop") || lowerMessage.contains("docker daemon") || lowerMessage.contains("docker engine") || lowerMessage.contains("cannot connect to the docker daemon")) {
+            return StartupFailure.DOCKER_NOT_RUNNING;
+        }
+        if (lowerMessage.contains("docker executable") || lowerMessage.contains("no such file or directory") && lowerMessage.contains("docker")) {
+            return StartupFailure.DOCKER_NOT_INSTALLED;
+        }
+        if (lowerMessage.contains("port is already allocated") || lowerMessage.contains("address already in use") && lowerMessage.contains("3306")) {
+            return StartupFailure.DATABASE_PORT_IN_USE;
+        }
+        if (lowerMessage.contains("schema validation: missing table")) {
+            return StartupFailure.STALE_SCHEMA;
+        }
+        if (lowerMessage.contains("flyway") || lowerMessage.contains("migration")) {
+            return StartupFailure.FLYWAY_MIGRATION_FAILED;
+        }
+        if (lowerMessage.contains("datasource properties are required")) {
+            return StartupFailure.DATASOURCE_CONFIG_MISSING;
+        }
+        if (lowerMessage.contains("access denied for user") || lowerMessage.contains("communications link failure") || lowerMessage.contains("connection refused") || lowerMessage.contains("unable to determine dialect without jdbc metadata")) {
+            return StartupFailure.DATABASE_UNREACHABLE;
+        }
+        return StartupFailure.UNKNOWN;
+    }
+
+    private static Throwable deepestCause(Throwable throwable) {
+        Throwable current = throwable;
+        while (current.getCause() != null && current.getCause() != current) {
+            current = current.getCause();
+        }
+        return current;
+    }
+
+    private enum StartupFailure {
+        SERVER_PORT_IN_USE,
+        DOCKER_NOT_RUNNING,
+        DOCKER_NOT_INSTALLED,
+        DATABASE_PORT_IN_USE,
+        STALE_SCHEMA,
+        FLYWAY_MIGRATION_FAILED,
+        DATASOURCE_CONFIG_MISSING,
+        DATABASE_UNREACHABLE,
+        UNKNOWN
     }
 }
diff --git a/src/main/java/com/petshop/backend/DockerComposeSupport.java b/src/main/java/com/petshop/backend/DockerComposeSupport.java
new file mode 100644
index 00000000..2a1f4396
--- /dev/null
+++ b/src/main/java/com/petshop/backend/DockerComposeSupport.java
@@ -0,0 +1,164 @@
+package com.petshop.backend;
+
+import java.io.BufferedReader;
+import java.io.IOException;
+import java.io.InputStreamReader;
+import java.nio.file.Path;
+import java.nio.file.Paths;
+import java.util.ArrayList;
+import java.util.List;
+import java.util.Locale;
+
+final class DockerComposeSupport {
+
+    private final Path projectDir = Paths.get("").toAbsolutePath();
+
+    void ensureDockerAvailable() {
+        CommandResult versionResult = runCommand(List.of(resolveDockerExecutable(), "version"), false);
+        if (versionResult.exitCode != 0) {
+            throw new IllegalStateException(describeDockerFailure(versionResult.output));
+        }
+    }
+
+    void startDatabase() {
+        runCommand(composeCommand("up", "-d", "--wait", "db"));
+    }
+
+    void stopDatabase() {
+        runCommand(composeCommand("stop", "db"));
+    }
+
+    void resetDatabase() {
+        runCommand(composeCommand("down", "-v", "--remove-orphans"));
+        String volumeName = getDatabaseVolumeName();
+        if (volumeExists(volumeName)) {
+            runCommand(List.of(resolveDockerExecutable(), "volume", "rm", "-f", volumeName));
+        }
+    }
+
+    boolean isDatabaseRunning() {
+        CommandResult result = runCommand(composeCommand("ps", "--status", "running", "--services", "db"), false);
+        if (result.exitCode != 0) {
+            return false;
+        }
+        return result.output.lines()
+                .map(String::trim)
+                .anyMatch("db"::equals);
+    }
+
+    private boolean volumeExists(String volumeName) {
+        CommandResult result = runCommand(List.of(resolveDockerExecutable(), "volume", "ls", "--format", "{{.Name}}"), false);
+        if (result.exitCode != 0) {
+            return false;
+        }
+        return result.output.lines()
+                .map(String::trim)
+                .anyMatch(volumeName::equals);
+    }
+
+    private String getDatabaseVolumeName() {
+        return projectDir.getFileName().toString() + "_db_data";
+    }
+
+    private List<String> composeCommand(String... args) {
+        List<String> command = new ArrayList<>();
+        command.add(resolveDockerExecutable());
+        command.add("compose");
+        command.add("-f");
+        command.add("docker-compose.dev.yml");
+        for (String arg : args) {
+            command.add(arg);
+        }
+        return command;
+    }
+
+    private String resolveDockerExecutable() {
+        String os = System.getProperty("os.name", "").toLowerCase(Locale.ROOT);
+        if (os.contains("win")) {
+            return "docker.exe";
+        }
+        return "docker";
+    }
+
+    private void runCommand(List<String> command) {
+        CommandResult result = runCommand(command, true);
+        if (result.exitCode != 0) {
+            throw new IllegalStateException(describeCommandFailure(command, result.output));
+        }
+    }
+
+    private CommandResult runCommand(List<String> command, boolean printOutput) {
+        ProcessBuilder builder = new ProcessBuilder(command);
+        builder.directory(projectDir.toFile());
+        builder.redirectErrorStream(true);
+
+        try {
+            Process process = builder.start();
+            StringBuilder output = new StringBuilder();
+            try (BufferedReader reader = new BufferedReader(new InputStreamReader(process.getInputStream()))) {
+                String line;
+                while ((line = reader.readLine()) != null) {
+                    output.append(line).append(System.lineSeparator());
+                    if (printOutput) {
+                        System.out.println(line);
+                    }
+                }
+            }
+            int exitCode = process.waitFor();
+            return new CommandResult(exitCode, output.toString().trim());
+        } catch (IOException ex) {
+            String executable = command.isEmpty() ? "docker" : command.getFirst();
+            throw new IllegalStateException("Unable to run " + executable + ". Install Docker Desktop and make sure it is available on PATH.", ex);
+        } catch (InterruptedException ex) {
+            Thread.currentThread().interrupt();
+            throw new IllegalStateException("Docker command interrupted", ex);
+        }
+    }
+
+    private String describeDockerFailure(String output) {
+        String lowerOutput = "";
+        if (output != null) {
+            lowerOutput = output.toLowerCase(Locale.ROOT);
+        }
+        if (lowerOutput.contains("docker desktop") || lowerOutput.contains("docker daemon") || lowerOutput.contains("docker engine") || lowerOutput.contains("cannot connect")) {
+            return "Docker Desktop is not running. Start Docker Desktop and rerun the command.";
+        }
+        if (output == null || output.isBlank()) {
+            return "Docker is unavailable. Start Docker Desktop and rerun the command.";
+        }
+        return output;
+    }
+
+    private String describeCommandFailure(List<String> command, String output) {
+        String renderedCommand = String.join(" ", command);
+        String lowerOutput = "";
+        if (output != null) {
+            lowerOutput = output.toLowerCase(Locale.ROOT);
+        }
+        if (renderedCommand.contains(" up ") || renderedCommand.endsWith(" up -d --wait db")) {
+            if (lowerOutput.contains("port is already allocated") || lowerOutput.contains("address already in use")) {
+                return "Database startup failed because port 3306 is already in use. Stop the conflicting MySQL service or container, then run Reset Database.";
+            }
+            if (lowerOutput.contains("docker desktop") || lowerOutput.contains("docker daemon") || lowerOutput.contains("docker engine")) {
+                return "Database startup failed because Docker Desktop is not running.";
+            }
+            if (output == null || output.isBlank()) {
+                return "Database startup failed while bringing up the Docker MySQL container.";
+            }
+            return output;
+        }
+        if (renderedCommand.contains(" volume rm ")) {
+            if (output == null || output.isBlank()) {
+                return "Database reset failed while removing the Docker volume.";
+            }
+            return output;
+        }
+        if (output == null || output.isBlank()) {
+            return "Command failed: " + renderedCommand;
+        }
+        return output;
+    }
+
+    private record CommandResult(int exitCode, String output) {
+    }
+}
diff --git a/src/main/java/com/petshop/backend/ResetDatabaseApplication.java b/src/main/java/com/petshop/backend/ResetDatabaseApplication.java
new file mode 100644
index 00000000..056ec36e
--- /dev/null
+++ b/src/main/java/com/petshop/backend/ResetDatabaseApplication.java
@@ -0,0 +1,10 @@
+package com.petshop.backend;
+
+public class ResetDatabaseApplication {
+
+    public static void main(String[] args) {
+        DockerComposeSupport docker = new DockerComposeSupport();
+        docker.ensureDockerAvailable();
+        docker.resetDatabase();
+    }
+}