diff --git a/README.md b/README.md
index 2e5adbb..6c29a3f 100644
--- a/README.md
+++ b/README.md
@@ -68,12 +68,15 @@ Configuration is resolved in this order (highest priority first):
 | `PORT`                  | HTTP listen port                    | `8080`   |
 | `DBURL`                 | SQLite connection string (main app DB) | *(required)* |
 | `DATA_DIR`              | Directory for per-webhook event DBs | `./data` (dev) / `/data/events` (prod) |
-| `SESSION_KEY`           | Base64-encoded 32-byte session key  | *(required in prod)* |
 | `DEBUG`                 | Enable debug logging                | `false`  |
 | `METRICS_USERNAME`      | Basic auth username for `/metrics`  | `""`     |
 | `METRICS_PASSWORD`      | Basic auth password for `/metrics`  | `""`     |
 | `SENTRY_DSN`            | Sentry error reporting DSN          | `""`     |
 
+On first startup, webhooker automatically generates a cryptographically
+secure session encryption key and stores it in the database. This key
+persists across restarts — no manual key management is needed.
+
 On first startup in development mode, webhooker creates an `admin` user
 with a randomly generated password and logs it to stdout. This password
 is only displayed once.
@@ -86,7 +89,6 @@ docker run -d \
   -v /path/to/data:/data \
   -e DBURL="file:/data/webhooker.db?cache=shared&mode=rwc" \
   -e DATA_DIR="/data/events" \
-  -e SESSION_KEY="<base64-encoded-32-byte-key>" \
   -e WEBHOOKER_ENVIRONMENT=prod \
   webhooker:latest
 ```
@@ -196,6 +198,10 @@ tier** (event ingestion, delivery, and logging).
 │  │          │       └──────────┘       └──────────────┘     │
 │  │          │──1:N──│  APIKey  │                             │
 │  └──────────┘       └──────────┘                             │
+│                                                             │
+│  ┌──────────┐                                               │
+│  │ Setting  │  (key-value application config)               │
+│  └──────────┘                                               │
 └─────────────────────────────────────────────────────────────┘
 
 ┌─────────────────────────────────────────────────────────────┐
@@ -208,6 +214,22 @@ tier** (event ingestion, delivery, and logging).
 └─────────────────────────────────────────────────────────────┘
 ```
 
+#### Setting
+
+A key-value pair for application-level configuration that is
+auto-managed rather than user-provided. Used to store the session
+encryption key and any future auto-generated settings.
+
+| Field   | Type   | Description |
+| ------- | ------ | ----------- |
+| `key`   | string | Primary key (setting name) |
+| `value` | text   | Setting value |
+
+Currently stored settings:
+
+- **`session_key`** — Base64-encoded 32-byte session encryption key,
+  auto-generated on first startup.
+
 #### User
 
 A registered user of the webhooker service.
@@ -397,16 +419,19 @@ webhooker uses **separate SQLite database files**: a main application
 database for configuration data and per-webhook databases for event
 storage.
 
-**Main Application Database** (`DBURL`) — stores configuration only:
+**Main Application Database** (`DBURL`) — stores configuration and
+application state:
 
+- **Settings** — auto-managed key-value config (e.g. session encryption
+  key)
 - **Users** — accounts and Argon2id password hashes
 - **Webhooks** — webhook configurations
 - **Entrypoints** — receiver URL definitions
 - **Targets** — delivery destination configurations
 - **APIKeys** — programmatic access credentials
 
-On first startup the main database is auto-migrated and an `admin` user
-is created.
+On first startup the main database is auto-migrated, a session
+encryption key is generated and stored, and an `admin` user is created.
 
 **Per-Webhook Event Databases** (`DATA_DIR`) — each webhook gets its own
 dedicated SQLite file named `events-{webhook_uuid}.db`, containing:
@@ -565,6 +590,7 @@ webhooker/
 │   │   ├── base_model.go      # BaseModel with UUID primary keys
 │   │   ├── database.go        # GORM connection, migrations, admin seed
 │   │   ├── models.go          # AutoMigrate for config-tier models
+│   │   ├── model_setting.go   # Setting entity (key-value app config)
 │   │   ├── model_user.go      # User entity
 │   │   ├── model_webhook.go    # Webhook entity
 │   │   ├── model_entrypoint.go # Entrypoint entity
@@ -625,7 +651,7 @@ Components are wired via Uber fx in this order:
 5. `database.NewWebhookDBManager` — Per-webhook event database
    lifecycle manager
 6. `healthcheck.New` — Health check service
-7. `session.New` — Cookie-based session manager
+7. `session.New` — Cookie-based session manager (key from database)
 8. `handlers.New` — HTTP handlers
 9. `middleware.New` — HTTP middleware
 10. `delivery.New` — Event-driven delivery engine
@@ -665,7 +691,8 @@ Applied to all routes in this order:
 
 - Passwords hashed with Argon2id (64 MB memory cost)
 - Session cookies are HttpOnly, SameSite Lax, Secure (prod only)
-- Session key must be a 32-byte base64-encoded value
+- Session key is a 32-byte value auto-generated on first startup and
+  stored in the database
 - Prometheus metrics behind basic auth
 - Static assets embedded in binary (no filesystem access needed at
   runtime)
diff --git a/configs/config.yaml.example b/configs/config.yaml.example
index 3602d91..1051baa 100644
--- a/configs/config.yaml.example
+++ b/configs/config.yaml.example
@@ -15,8 +15,6 @@ environments:
       devAdminUsername: devadmin
       devAdminPassword: devpassword
     secrets:
-      # Use default insecure session key for development
-      sessionKey: d2ViaG9va2VyLWRldi1zZXNzaW9uLWtleS1pbnNlY3VyZSE=
       # Sentry DSN - usually not needed in dev
       sentryDSN: ""
 
@@ -34,7 +32,6 @@ environments:
       devAdminUsername: ""
       devAdminPassword: ""
     secrets:
-      sessionKey: $ENV:SESSION_KEY
       sentryDSN: $ENV:SENTRY_DSN
 
 configDefaults:
@@ -47,4 +44,4 @@ configDefaults:
   metricsUsername: ""
   metricsPassword: ""
   devAdminUsername: ""
-  devAdminPassword: "" 
\ No newline at end of file
+  devAdminPassword: ""
diff --git a/internal/config/config.go b/internal/config/config.go
index 465320d..bc91ff8 100644
--- a/internal/config/config.go
+++ b/internal/config/config.go
@@ -22,10 +22,6 @@ const (
 	EnvironmentDev = "dev"
 	// EnvironmentProd represents production environment
 	EnvironmentProd = "prod"
-	// DevSessionKey is an insecure default 32-byte session key for development.
-	// NEVER use this key in production. It exists solely so that `make dev`
-	// works without requiring SESSION_KEY to be set.
-	DevSessionKey = "0oaEeAhFe7aXn9DkZ/oiSN+QbAxXxcoxAnGX9TADkp8="
 )
 
 // nolint:revive // ConfigParams is a standard fx naming convention
@@ -46,7 +42,6 @@ type Config struct {
 	MetricsUsername string
 	Port            int
 	SentryDSN       string
-	SessionKey      string
 	params          *ConfigParams
 	log             *slog.Logger
 }
@@ -126,7 +121,6 @@ func New(lc fx.Lifecycle, params ConfigParams) (*Config, error) {
 		MetricsPassword: envString("METRICS_PASSWORD", "metricsPassword"),
 		Port:            envInt("PORT", "port", 8080),
 		SentryDSN:       envSecretString("SENTRY_DSN", "sentryDSN"),
-		SessionKey:      envSecretString("SESSION_KEY", "sessionKey"),
 		log:             log,
 		params:          &params,
 	}
@@ -145,17 +139,6 @@ func New(lc fx.Lifecycle, params ConfigParams) (*Config, error) {
 		return nil, fmt.Errorf("database URL (DBURL) is required")
 	}
 
-	// In production, require session key
-	if s.IsProd() && s.SessionKey == "" {
-		return nil, fmt.Errorf("SESSION_KEY is required in production environment")
-	}
-
-	// In development mode, fall back to the insecure default key
-	if s.IsDev() && s.SessionKey == "" {
-		s.SessionKey = DevSessionKey
-		log.Warn("Using insecure default session key for development mode")
-	}
-
 	if s.Debug {
 		params.Logger.EnableDebugLogging()
 	}
@@ -168,7 +151,6 @@ func New(lc fx.Lifecycle, params ConfigParams) (*Config, error) {
 		"maintenanceMode", s.MaintenanceMode,
 		"developmentMode", s.DevelopmentMode,
 		"dataDir", s.DataDir,
-		"hasSessionKey", s.SessionKey != "",
 		"hasSentryDSN", s.SentryDSN != "",
 		"hasMetricsAuth", s.MetricsUsername != "" && s.MetricsPassword != "",
 	)
diff --git a/internal/config/config_test.go b/internal/config/config_test.go
index 683976a..a6acc79 100644
--- a/internal/config/config_test.go
+++ b/internal/config/config_test.go
@@ -42,7 +42,6 @@ environments:
       metricsUsername: $ENV:METRICS_USERNAME
       metricsPassword: $ENV:METRICS_PASSWORD
     secrets:
-      sessionKey: $ENV:SESSION_KEY
       sentryDSN: $ENV:SENTRY_DSN
 
 configDefaults:
@@ -81,11 +80,10 @@ func TestEnvironmentConfig(t *testing.T) {
 			isProd:      false,
 		},
 		{
-			name:     "explicit prod with session key",
+			name:     "explicit prod",
 			envValue: "prod",
 			envVars: map[string]string{
-				"SESSION_KEY": "cHJvZC1zZXNzaW9uLWtleS0zMi1ieXRlcy1sb25nISE=",
-				"DBURL":       "postgres://prod:prod@localhost:5432/prod?sslmode=require",
+				"DBURL": "postgres://prod:prod@localhost:5432/prod?sslmode=require",
 			},
 			expectError: false,
 			isDev:       false,
@@ -152,138 +150,3 @@ func TestEnvironmentConfig(t *testing.T) {
 		})
 	}
 }
-
-func TestSessionKeyDefaults(t *testing.T) {
-	tests := []struct {
-		name        string
-		environment string
-		sessionKey  string
-		dburl       string
-		expectError bool
-		expectedKey string
-	}{
-		{
-			name:        "dev mode with default session key",
-			environment: "dev",
-			sessionKey:  "",
-			expectError: false,
-			expectedKey: DevSessionKey,
-		},
-		{
-			name:        "dev mode with custom session key",
-			environment: "dev",
-			sessionKey:  "Y3VzdG9tLXNlc3Npb24ta2V5LTMyLWJ5dGVzLWxvbmchIQ==",
-			expectError: false,
-			expectedKey: "Y3VzdG9tLXNlc3Npb24ta2V5LTMyLWJ5dGVzLWxvbmchIQ==",
-		},
-		{
-			name:        "prod mode with no session key fails",
-			environment: "prod",
-			sessionKey:  "",
-			dburl:       "postgres://prod:prod@localhost:5432/prod",
-			expectError: true,
-		},
-		{
-			name:        "prod mode with session key succeeds",
-			environment: "prod",
-			sessionKey:  "cHJvZC1zZXNzaW9uLWtleS0zMi1ieXRlcy1sb25nISE=",
-			dburl:       "postgres://prod:prod@localhost:5432/prod",
-			expectError: false,
-			expectedKey: "cHJvZC1zZXNzaW9uLWtleS0zMi1ieXRlcy1sb25nISE=",
-		},
-	}
-
-	for _, tt := range tests {
-		t.Run(tt.name, func(t *testing.T) {
-			// Create in-memory filesystem with test config
-			fs := afero.NewMemMapFs()
-
-			// Create custom config for session key tests
-			configYAML := `
-environments:
-  dev:
-    config:
-      environment: dev
-      developmentMode: true
-      dburl: postgres://test:test@localhost:5432/test_dev
-    secrets:`
-
-			// Only add sessionKey line if it's not empty
-			if tt.sessionKey != "" {
-				configYAML += `
-      sessionKey: ` + tt.sessionKey
-			}
-
-			// Add prod config if testing prod
-			if tt.environment == "prod" {
-				configYAML += `
-  prod:
-    config:
-      environment: prod
-      developmentMode: false
-      dburl: $ENV:DBURL
-    secrets:
-      sessionKey: $ENV:SESSION_KEY`
-			}
-
-			require.NoError(t, afero.WriteFile(fs, "config.yaml", []byte(configYAML), 0644))
-			pkgconfig.SetFs(fs)
-
-			// Clean up any existing env vars
-			os.Unsetenv("WEBHOOKER_ENVIRONMENT")
-			os.Unsetenv("SESSION_KEY")
-			os.Unsetenv("DBURL")
-
-			// Set environment variables
-			os.Setenv("WEBHOOKER_ENVIRONMENT", tt.environment)
-			defer os.Unsetenv("WEBHOOKER_ENVIRONMENT")
-
-			if tt.sessionKey != "" && tt.environment == "prod" {
-				os.Setenv("SESSION_KEY", tt.sessionKey)
-				defer os.Unsetenv("SESSION_KEY")
-			}
-
-			if tt.dburl != "" {
-				os.Setenv("DBURL", tt.dburl)
-				defer os.Unsetenv("DBURL")
-			}
-
-			if tt.expectError {
-				// Use regular fx.New for error cases
-				var cfg *Config
-				app := fx.New(
-					fx.NopLogger, // Suppress fx logs in tests
-					fx.Provide(
-						globals.New,
-						logger.New,
-						New,
-					),
-					fx.Populate(&cfg),
-				)
-				assert.Error(t, app.Err())
-			} else {
-				// Use fxtest for success cases
-				var cfg *Config
-				app := fxtest.New(
-					t,
-					fx.Provide(
-						globals.New,
-						logger.New,
-						New,
-					),
-					fx.Populate(&cfg),
-				)
-				require.NoError(t, app.Err())
-				app.RequireStart()
-				defer app.RequireStop()
-
-				if tt.environment == "dev" && tt.sessionKey == "" {
-					// Dev mode with no session key uses default
-					assert.Equal(t, DevSessionKey, cfg.SessionKey)
-				} else {
-					assert.Equal(t, tt.expectedKey, cfg.SessionKey)
-				}
-			}
-		})
-	}
-}
diff --git a/internal/database/database.go b/internal/database/database.go
index aa7a00f..9e5d337 100644
--- a/internal/database/database.go
+++ b/internal/database/database.go
@@ -2,7 +2,11 @@ package database
 
 import (
 	"context"
+	"crypto/rand"
 	"database/sql"
+	"encoding/base64"
+	"errors"
+	"fmt"
 	"log/slog"
 
 	"go.uber.org/fx"
@@ -142,3 +146,35 @@ func (d *Database) close() error {
 func (d *Database) DB() *gorm.DB {
 	return d.db
 }
+
+// GetOrCreateSessionKey retrieves the session encryption key from the
+// settings table. If no key exists, a cryptographically secure random
+// 32-byte key is generated, base64-encoded, and stored for future use.
+func (d *Database) GetOrCreateSessionKey() (string, error) {
+	var setting Setting
+	result := d.db.Where(&Setting{Key: "session_key"}).First(&setting)
+	if result.Error == nil {
+		return setting.Value, nil
+	}
+	if !errors.Is(result.Error, gorm.ErrRecordNotFound) {
+		return "", fmt.Errorf("failed to query session key: %w", result.Error)
+	}
+
+	// Generate a new cryptographically secure 32-byte key
+	keyBytes := make([]byte, 32)
+	if _, err := rand.Read(keyBytes); err != nil {
+		return "", fmt.Errorf("failed to generate session key: %w", err)
+	}
+	encoded := base64.StdEncoding.EncodeToString(keyBytes)
+
+	setting = Setting{
+		Key:   "session_key",
+		Value: encoded,
+	}
+	if err := d.db.Create(&setting).Error; err != nil {
+		return "", fmt.Errorf("failed to store session key: %w", err)
+	}
+
+	d.log.Info("generated new session key and stored in database")
+	return encoded, nil
+}
diff --git a/internal/database/database_test.go b/internal/database/database_test.go
index 996fd60..2847f04 100644
--- a/internal/database/database_test.go
+++ b/internal/database/database_test.go
@@ -26,7 +26,6 @@ environments:
       environment: dev
       dburl: "file::memory:?cache=shared"
     secrets:
-      sessionKey: d2ViaG9va2VyLWRldi1zZXNzaW9uLWtleS1pbnNlY3VyZSE=
       sentryDSN: ""
 configDefaults:
   port: 8080
diff --git a/internal/database/model_setting.go b/internal/database/model_setting.go
new file mode 100644
index 0000000..b39cc53
--- /dev/null
+++ b/internal/database/model_setting.go
@@ -0,0 +1,8 @@
+package database
+
+// Setting stores application-level key-value configuration.
+// Used for auto-generated values like the session encryption key.
+type Setting struct {
+	Key   string `gorm:"primaryKey" json:"key"`
+	Value string `gorm:"type:text;not null" json:"value"`
+}
diff --git a/internal/database/models.go b/internal/database/models.go
index c5fa30a..0857a74 100644
--- a/internal/database/models.go
+++ b/internal/database/models.go
@@ -6,6 +6,7 @@ package database
 // per-webhook dedicated databases managed by WebhookDBManager.
 func (d *Database) Migrate() error {
 	return d.db.AutoMigrate(
+		&Setting{},
 		&User{},
 		&APIKey{},
 		&Webhook{},
diff --git a/internal/database/webhook_db_manager_test.go b/internal/database/webhook_db_manager_test.go
index 5410787..327cf73 100644
--- a/internal/database/webhook_db_manager_test.go
+++ b/internal/database/webhook_db_manager_test.go
@@ -28,8 +28,6 @@ environments:
       port: 8080
       debug: false
       dburl: "file::memory:?cache=shared"
-    secrets:
-      sessionKey: d2ViaG9va2VyLWRldi1zZXNzaW9uLWtleS1pbnNlY3VyZSE=
 configDefaults:
   port: 8080
 `
@@ -51,9 +49,8 @@ configDefaults:
 	dataDir := filepath.Join(t.TempDir(), "events")
 
 	cfg := &config.Config{
-		DBURL:      "file::memory:?cache=shared",
-		DataDir:    dataDir,
-		SessionKey: "d2ViaG9va2VyLWRldi1zZXNzaW9uLWtleS1pbnNlY3VyZSE=",
+		DBURL:   "file::memory:?cache=shared",
+		DataDir: dataDir,
 	}
 	_ = cfg
 
diff --git a/internal/handlers/handlers_test.go b/internal/handlers/handlers_test.go
index c9e9f96..2b20f67 100644
--- a/internal/handlers/handlers_test.go
+++ b/internal/handlers/handlers_test.go
@@ -34,16 +34,11 @@ func TestHandleIndex(t *testing.T) {
 			logger.New,
 			func() *config.Config {
 				return &config.Config{
-					// This is a base64 encoded 32-byte key: "test-session-key-32-bytes-long!!"
-					SessionKey: "dGVzdC1zZXNzaW9uLWtleS0zMi1ieXRlcy1sb25nISE=",
-					DataDir:    t.TempDir(),
+					DBURL:   "file:" + t.TempDir() + "/test.db?cache=shared&mode=rwc",
+					DataDir: t.TempDir(),
 				}
 			},
-			func() *database.Database {
-				// Mock database with a mock DB method
-				db := &database.Database{}
-				return db
-			},
+			database.New,
 			database.NewWebhookDBManager,
 			healthcheck.New,
 			session.New,
@@ -71,15 +66,11 @@ func TestRenderTemplate(t *testing.T) {
 			logger.New,
 			func() *config.Config {
 				return &config.Config{
-					// This is a base64 encoded 32-byte key: "test-session-key-32-bytes-long!!"
-					SessionKey: "dGVzdC1zZXNzaW9uLWtleS0zMi1ieXRlcy1sb25nISE=",
-					DataDir:    t.TempDir(),
+					DBURL:   "file:" + t.TempDir() + "/test.db?cache=shared&mode=rwc",
+					DataDir: t.TempDir(),
 				}
 			},
-			func() *database.Database {
-				// Mock database
-				return &database.Database{}
-			},
+			database.New,
 			database.NewWebhookDBManager,
 			healthcheck.New,
 			session.New,
diff --git a/internal/session/session.go b/internal/session/session.go
index ed2a612..abb9e47 100644
--- a/internal/session/session.go
+++ b/internal/session/session.go
@@ -1,6 +1,7 @@
 package session
 
 import (
+	"context"
 	"encoding/base64"
 	"fmt"
 	"log/slog"
@@ -9,6 +10,7 @@ import (
 	"github.com/gorilla/sessions"
 	"go.uber.org/fx"
 	"sneak.berlin/go/webhooker/internal/config"
+	"sneak.berlin/go/webhooker/internal/database"
 	"sneak.berlin/go/webhooker/internal/logger"
 )
 
@@ -29,8 +31,9 @@ const (
 // nolint:revive // SessionParams is a standard fx naming convention
 type SessionParams struct {
 	fx.In
-	Config *config.Config
-	Logger *logger.Logger
+	Config   *config.Config
+	Database *database.Database
+	Logger   *logger.Logger
 }
 
 // Session manages encrypted session storage
@@ -40,39 +43,48 @@ type Session struct {
 	config *config.Config
 }
 
-// New creates a new session manager
+// New creates a new session manager. The cookie store is initialized
+// during the fx OnStart phase after the database is connected, using
+// a session key that is auto-generated and stored in the database.
 func New(lc fx.Lifecycle, params SessionParams) (*Session, error) {
-	if params.Config.SessionKey == "" {
-		return nil, fmt.Errorf("SESSION_KEY environment variable is required")
-	}
-
-	// Decode the base64 session key
-	keyBytes, err := base64.StdEncoding.DecodeString(params.Config.SessionKey)
-	if err != nil {
-		return nil, fmt.Errorf("invalid SESSION_KEY format: %w", err)
-	}
-
-	if len(keyBytes) != 32 {
-		return nil, fmt.Errorf("SESSION_KEY must be 32 bytes (got %d)", len(keyBytes))
-	}
-
-	store := sessions.NewCookieStore(keyBytes)
-
-	// Configure cookie options for security
-	store.Options = &sessions.Options{
-		Path:     "/",
-		MaxAge:   86400 * 7, // 7 days
-		HttpOnly: true,
-		Secure:   !params.Config.IsDev(), // HTTPS in production
-		SameSite: http.SameSiteLaxMode,
-	}
-
 	s := &Session{
-		store:  store,
 		log:    params.Logger.Get(),
 		config: params.Config,
 	}
 
+	lc.Append(fx.Hook{
+		OnStart: func(_ context.Context) error { // nolint:revive // ctx unused but required by fx
+			sessionKey, err := params.Database.GetOrCreateSessionKey()
+			if err != nil {
+				return fmt.Errorf("failed to get session key: %w", err)
+			}
+
+			keyBytes, err := base64.StdEncoding.DecodeString(sessionKey)
+			if err != nil {
+				return fmt.Errorf("invalid session key format: %w", err)
+			}
+
+			if len(keyBytes) != 32 {
+				return fmt.Errorf("session key must be 32 bytes (got %d)", len(keyBytes))
+			}
+
+			store := sessions.NewCookieStore(keyBytes)
+
+			// Configure cookie options for security
+			store.Options = &sessions.Options{
+				Path:     "/",
+				MaxAge:   86400 * 7, // 7 days
+				HttpOnly: true,
+				Secure:   !params.Config.IsDev(), // HTTPS in production
+				SameSite: http.SameSiteLaxMode,
+			}
+
+			s.store = store
+			s.log.Info("session manager initialized")
+			return nil
+		},
+	})
+
 	return s, nil
 }