diff --git a/src/Turnierplan.App/Constants/TurnierplanVersion.cs b/src/Turnierplan.App/Constants/TurnierplanVersion.cs
index baac625e..8ed87dc7 100644
--- a/src/Turnierplan.App/Constants/TurnierplanVersion.cs
+++ b/src/Turnierplan.App/Constants/TurnierplanVersion.cs
@@ -1,13 +1,46 @@
+using System.Text.RegularExpressions;
+
 namespace Turnierplan.App.Constants;
 
-internal static class TurnierplanVersion
+internal static partial class TurnierplanVersion
 {
-    public static readonly string Version = DetermineVersion();
+    public static readonly bool IsVersionAvailable;
+
+    public static readonly string Version;
+
+    public static readonly int Major;
+    public static readonly int Minor;
+    public static readonly int Patch;
 
-    private static string DetermineVersion()
+    static TurnierplanVersion()
     {
         var assemblyVersion = typeof(TurnierplanVersion).Assembly.GetName().Version?.ToString();
 
-        return assemblyVersion?[..assemblyVersion.LastIndexOf('.')] ?? "?.?.?";
+        if (assemblyVersion is null)
+        {
+            IsVersionAvailable = false;
+            Version = "?.?.?";
+
+            return;
+        }
+
+        var match = VersionRegex().Match(assemblyVersion);
+
+        if (!match.Success)
+        {
+            IsVersionAvailable = false;
+            Version = "?.?.?";
+
+            return;
+        }
+
+        IsVersionAvailable = true;
+        Major = int.Parse(match.Groups["Major"].Value);
+        Minor = int.Parse(match.Groups["Minor"].Value);
+        Patch = int.Parse(match.Groups["Patch"].Value);
+        Version = $"{Major}.{Minor}.{Patch}";
     }
+
+    [GeneratedRegex(@"^(?<Major>\d+)\.(?<Minor>\d+)\.(?<Patch>\d+)\.\d+$")]
+    private static partial Regex VersionRegex();
 }
diff --git a/src/Turnierplan.App/Extensions/WebApplicationExtensions.cs b/src/Turnierplan.App/Extensions/WebApplicationExtensions.cs
index eb1693ec..e652ec13 100644
--- a/src/Turnierplan.App/Extensions/WebApplicationExtensions.cs
+++ b/src/Turnierplan.App/Extensions/WebApplicationExtensions.cs
@@ -1,6 +1,8 @@
 using Microsoft.AspNetCore.Identity;
 using Microsoft.EntityFrameworkCore;
 using Microsoft.Extensions.Options;
+using Npgsql;
+using Turnierplan.App.Constants;
 using Turnierplan.App.Options;
 using Turnierplan.Core.User;
 using Turnierplan.Dal;
@@ -24,22 +26,84 @@ public static async Task InitializeDatabaseAsync(this WebApplication app)
 
         if (context.Database.IsNpgsql())
         {
-            // If the database is in-memory, no migration is necessary
+            // If the database is in-memory, no migration or downgrade check is necessary
             await context.Database.MigrateAsync();
+            await EnsureNoDowngradeAsync(context, logger);
         }
 
+        await EnsureInitialUserCreatedAsync(scope.ServiceProvider, context, logger);
+    }
+
+    private static async Task EnsureNoDowngradeAsync(TurnierplanContext context, ILogger<DatabaseMigrator> logger)
+    {
+        const string schema = TurnierplanContext.Schema;
+
+        if (!TurnierplanVersion.IsVersionAvailable)
+        {
+            throw new InvalidOperationException("Downgrade check failed because the current version is not available.");
+        }
+
+        /* The version check works by creating a special table which stores all turnierplan.NET versions that have ever
+         * been run on this database along with the corresponding timestamp. Then, we try to insert a new row with the
+         * current version - doing nothing if a row for that specific version already exists. Finally, we query the row
+         * with the most recent version. If that version does not match the version we are currently running, a version
+         * downgrade has occurred, and we stop the application from continuing execution. */
+
+        // The transaction is necessary because otherwise, we will save invalid
+        // version history entries to the database in the case of a version downgrade.
+        await context.Database.BeginTransactionAsync();
+
+        var versionParameter = new NpgsqlParameter("version", TurnierplanVersion.Version);
+        var majorParameter = new NpgsqlParameter("major", TurnierplanVersion.Major);
+        var minorParameter = new NpgsqlParameter("minor", TurnierplanVersion.Minor);
+        var patchParameter = new NpgsqlParameter("patch", TurnierplanVersion.Patch);
+
+        await context.Database.ExecuteSqlRawAsync($"""
+CREATE TABLE IF NOT EXISTS {schema}."__TPVersionHistory" (
+    "Version"   text NOT NULL UNIQUE,
+    "Major"     integer NOT NULL,
+    "Minor"     integer NOT NULL,
+    "Patch"     integer NOT NULL,
+    "Timestamp" timestamp with time zone NOT NULL
+);
+
+INSERT INTO {schema}."__TPVersionHistory" ("Version", "Major", "Minor", "Patch", "Timestamp")
+    VALUES (@version, @major, @minor, @patch, now())
+    ON CONFLICT DO NOTHING;
+""", versionParameter, majorParameter, minorParameter, patchParameter);
+
+        var mostRecentVersion = await context.Database.SqlQueryRaw<VersionHistory>($"SELECT * FROM {schema}.\"__TPVersionHistory\"")
+            .OrderByDescending(x => x.Major)
+            .ThenByDescending(x => x.Minor)
+            .ThenByDescending(x => x.Patch)
+            .FirstAsync();
+
+        if (!mostRecentVersion.Version.Equals(TurnierplanVersion.Version))
+        {
+            logger.LogCritical("Detected version downgrade from '{MostRecentVersion}' to '{CurrentVersion}'.", mostRecentVersion.Version, TurnierplanVersion.Version);
+            Environment.Exit(1);
+
+            return;
+        }
+
+        // Commit only after we know that the current version is "valid"
+        await context.Database.CommitTransactionAsync();
+    }
+
+    private static async Task EnsureInitialUserCreatedAsync(IServiceProvider serviceProvider, TurnierplanContext context, ILogger<DatabaseMigrator> logger)
+    {
         var userCount = await context.Users.CountAsync();
 
         if (userCount == 0)
         {
-            var options = scope.ServiceProvider.GetRequiredService<IOptions<TurnierplanOptions>>().Value;
+            var options = serviceProvider.GetRequiredService<IOptions<TurnierplanOptions>>().Value;
 
             var overwriteInitialUserPassword = !string.IsNullOrWhiteSpace(options.InitialUserPassword);
 
             var initialUserName = string.IsNullOrWhiteSpace(options.InitialUserName) ? "admin" : options.InitialUserName;
             var initialUserPassword = overwriteInitialUserPassword ? options.InitialUserPassword! : Guid.NewGuid().ToString();
 
-            var passwordHasher = scope.ServiceProvider.GetRequiredService<IPasswordHasher<User>>();
+            var passwordHasher = serviceProvider.GetRequiredService<IPasswordHasher<User>>();
 
             var initialUser = new User(initialUserName)
             {
@@ -69,4 +133,6 @@ public static async Task InitializeDatabaseAsync(this WebApplication app)
     }
 
     private sealed record DatabaseMigrator;
+
+    private sealed record VersionHistory(string Version, int Major, int Minor, int Patch);
 }