diff --git a/AGENTS.md b/AGENTS.md
new file mode 100644
index 0000000..a888b37
--- /dev/null
+++ b/AGENTS.md
@@ -0,0 +1,327 @@
+# AGENTS.md - Developer Guide for oslstats
+
+This document provides guidelines for AI coding agents and developers working on the oslstats codebase.
+
+## Project Overview
+
+**Module**: `git.haelnorr.com/h/oslstats`  
+**Language**: Go 1.25.5  
+**Architecture**: Web application with Discord OAuth, PostgreSQL database, templ templates  
+**Key Technologies**: Bun ORM, templ, TailwindCSS, custom golib libraries
+
+## Build, Test, and Development Commands
+
+### Building
+```bash
+# Full production build (tailwind → templ → go generate → go build)
+make build
+
+# Build and run
+make run
+
+# Clean build artifacts
+make clean
+```
+
+### Development Mode
+```bash
+# Watch mode with hot reload (templ, air, tailwindcss in parallel)
+make dev
+
+# Development server runs on:
+# - Proxy: http://localhost:3000 (use this)
+# - App: http://localhost:3333 (internal)
+```
+
+### Testing
+```bash
+# Run all tests
+go test ./...
+
+# Run tests for a specific package
+go test ./pkg/oauth
+
+# Run a single test function
+go test ./pkg/oauth -run TestGenerateState_Success
+
+# Run tests with verbose output
+go test -v ./pkg/oauth
+
+# Run tests with coverage
+go test -cover ./...
+go test -coverprofile=coverage.out ./...
+go tool cover -html=coverage.out
+```
+
+### Database
+```bash
+# Run migrations
+make migrate
+# OR
+./bin/oslstats --migrate
+```
+
+### Configuration Management
+```bash
+# Generate .env template file
+make genenv
+# OR with custom output: make genenv OUT=.env.example
+
+# Show environment variable documentation
+make envdoc
+
+# Show current environment values
+make showenv
+```
+
+## Code Style Guidelines
+
+### Import Organization
+Organize imports in **3 groups** separated by blank lines:
+
+```go
+import (
+    // 1. Standard library
+    "context"
+    "net/http"
+    "fmt"
+    
+    // 2. External dependencies
+    "git.haelnorr.com/h/golib/hws"
+    "github.com/pkg/errors"
+    "github.com/uptrace/bun"
+    
+    // 3. Internal packages
+    "git.haelnorr.com/h/oslstats/internal/config"
+    "git.haelnorr.com/h/oslstats/pkg/oauth"
+)
+```
+
+### Naming Conventions
+
+**Variables**:
+- Local: `camelCase` (userAgentKey, httpServer, dbConn)
+- Exported: `PascalCase` (Config, User, Token)
+- Common abbreviations: `cfg`, `ctx`, `tx`, `db`, `err`, `w`, `r`
+
+**Functions**:
+- Exported: `PascalCase` (GetConfig, NewStore, GenerateState)
+- Private: `camelCase` (throwError, shouldShowDetails, loadModels)
+- HTTP handlers: Return `http.Handler`, use dependency injection pattern
+- Database functions: Use `bun.Tx` as parameter for transactions
+
+**Types**:
+- Structs/Interfaces: `PascalCase` (Config, User, OAuthSession)
+- Use `-er` suffix for interfaces (implied from usage)
+
+**Files**:
+- Prefer single word: `config.go`, `oauth.go`, `errors.go`
+- Use snake_case if needed: `discord_tokens.go`, `state_test.go`
+- Test files: `*_test.go` alongside source files
+
+### Error Handling
+
+**Always wrap errors** with context using `github.com/pkg/errors`:
+
+```go
+if err != nil {
+    return errors.Wrap(err, "operation_name")
+}
+```
+
+**Validate inputs at function start**:
+```go
+func DoSomething(cfg *Config, data string) error {
+    if cfg == nil {
+        return errors.New("cfg cannot be nil")
+    }
+    if data == "" {
+        return errors.New("data cannot be empty")
+    }
+    // ... rest of function
+}
+```
+
+**HTTP error helpers** (in handlers package):
+- `throwInternalServiceError(s, w, r, msg, err)` - 500 errors
+- `throwBadRequest(s, w, r, msg, err)` - 400 errors
+- `throwForbidden(s, w, r, msg, err)` - 403 errors (normal)
+- `throwForbiddenSecurity(s, w, r, msg, err)` - 403 security violations (WARN level)
+- `throwUnauthorized(s, w, r, msg, err)` - 401 errors (normal)
+- `throwUnauthorizedSecurity(s, w, r, msg, err)` - 401 security violations (WARN level)
+- `throwNotFound(s, w, r, path)` - 404 errors
+
+### Common Patterns
+
+**HTTP Handler Pattern**:
+```go
+func HandlerName(server *hws.Server, deps ...) http.Handler {
+    return http.HandlerFunc(
+        func(w http.ResponseWriter, r *http.Request) {
+            // Handler logic here
+        },
+    )
+}
+```
+
+**Database Operation Pattern**:
+```go
+func GetSomething(ctx context.Context, tx bun.Tx, id int) (*Result, error) {
+    result := new(Result)
+    err := tx.NewSelect().
+        Model(result).
+        Where("id = ?", id).
+        Scan(ctx)
+    if err != nil {
+        if err.Error() == "sql: no rows in result set" {
+            return nil, nil  // Return nil, nil for not found
+        }
+        return nil, errors.Wrap(err, "tx.Select")
+    }
+    return result, nil
+}
+```
+
+**Setup Function Pattern** (returns instance, cleanup func, error):
+```go
+func setupSomething(ctx context.Context, cfg *Config) (*Type, func() error, error) {
+    instance := newInstance()
+    
+    err := configure(instance)
+    if err != nil {
+        return nil, nil, errors.Wrap(err, "configure")
+    }
+    
+    return instance, instance.Close, nil
+}
+```
+
+**Configuration Pattern** (using ezconf):
+```go
+type Config struct {
+    Field string // ENV FIELD_NAME: Description (required/default: value)
+}
+
+func ConfigFromEnv() (any, error) {
+    cfg := &Config{
+        Field: env.String("FIELD_NAME", "default"),
+    }
+    // Validation here
+    return cfg, nil
+}
+```
+
+### Formatting & Types
+
+**Formatting**:
+- Use `gofmt` (standard Go formatting)
+- No tabs vs spaces debate - Go uses tabs
+
+**Types**:
+- Prefer explicit types over inference when it improves clarity
+- Use struct tags for ORM and JSON marshaling:
+  ```go
+  type User struct {
+      bun.BaseModel `bun:"table:users,alias:u"`
+      ID           int    `bun:"id,pk,autoincrement"`
+      Username     string `bun:"username,unique"`
+      AccessToken  string `json:"access_token"`
+  }
+  ```
+
+**Comments**:
+- Document exported functions and types
+- Use inline comments for ENV var documentation in Config structs
+- Explain security-critical code flows
+
+### Testing
+
+**Test File Location**: Place `*_test.go` files alongside source files
+
+**Test Naming**:
+```go
+func TestFunctionName_Scenario(t *testing.T)
+func TestGenerateState_Success(t *testing.T)
+func TestVerifyState_WrongUserAgentKey(t *testing.T)
+```
+
+**Test Structure**:
+- Use subtests with `t.Run()` for related scenarios
+- Use table-driven tests for multiple similar cases
+- Create helper functions for common setup (e.g., `testConfig()`)
+- Test happy paths, error cases, edge cases, and security properties
+
+**Test Categories** (from pkg/oauth/state_test.go example):
+1. Happy path tests
+2. Error handling (nil params, empty fields, malformed input)
+3. Security tests (MITM, CSRF, replay attacks, tampering)
+4. Edge cases (concurrency, constant-time comparison)
+5. Integration tests (round-trip verification)
+
+### Security
+
+**Critical Practices**:
+- Use `crypto/subtle.ConstantTimeCompare` for cryptographic comparisons
+- Implement CSRF protection via state tokens
+- Store sensitive cookies as HttpOnly
+- Use separate logging levels for security violations (WARN)
+- Validate all inputs at function boundaries
+- Use parameterized queries (Bun ORM handles this)
+- Never commit secrets (.env, keys/ are gitignored)
+
+## Project Structure
+
+```
+oslstats/
+├── cmd/oslstats/          # Application entry point
+│   ├── main.go            # Entry point with flag parsing
+│   ├── run.go             # Server initialization & graceful shutdown
+│   ├── httpserver.go      # HTTP server setup
+│   ├── routes.go          # Route registration
+│   ├── middleware.go      # Middleware registration
+│   ├── auth.go            # Authentication setup
+│   └── db.go              # Database connection & migrations
+├── internal/              # Private application code
+│   ├── config/            # Configuration aggregation
+│   ├── db/                # Database models & queries (Bun ORM)
+│   ├── discord/           # Discord OAuth integration
+│   ├── handlers/          # HTTP request handlers
+│   ├── session/           # Session store (in-memory)
+│   └── view/              # Templ templates
+│       ├── component/     # Reusable UI components
+│       ├── layout/        # Page layouts
+│       └── page/          # Full pages
+├── pkg/                   # Reusable packages
+│   ├── contexts/          # Context key definitions
+│   ├── embedfs/           # Embedded static files
+│   └── oauth/             # OAuth state management
+├── bin/                   # Compiled binaries (gitignored)
+├── keys/                  # Private keys (gitignored)
+├── tmp/                   # Air hot reload temp files (gitignored)
+├── Makefile               # Build automation
+├── .air.toml              # Hot reload configuration
+└── go.mod                 # Go module definition
+```
+
+## Key Dependencies
+
+- **git.haelnorr.com/h/golib/*** - Custom libraries (env, ezconf, hlog, hws, hwsauth, cookies, jwt)
+- **github.com/a-h/templ** - Type-safe HTML templating
+- **github.com/uptrace/bun** - PostgreSQL ORM
+- **github.com/bwmarrin/discordgo** - Discord API client
+- **github.com/pkg/errors** - Error wrapping (use this, not fmt.Errorf)
+- **github.com/joho/godotenv** - .env file loading
+
+## Notes for AI Agents
+
+1. **Never commit** .env files, keys/, or generated files (*_templ.go, output.css)
+2. **Database operations** should use `bun.Tx` for transaction safety
+3. **Templates** are written in templ, not Go html/template - run `templ generate` after changes
+4. **Static files** are embedded via `//go:embed` - check pkg/embedfs/
+5. **Error messages** should be descriptive and use errors.Wrap for context
+6. **Security is critical** - especially in OAuth flows (see pkg/oauth/state_test.go for examples)
+7. **Air proxy** runs on port 3000 during development; app runs on 3333
+8. **Test coverage** is currently limited - prioritize testing security-critical code
+9. **Configuration** uses ezconf pattern - see internal/*/ezconf.go files for examples
+10. **Graceful shutdown** is implemented in cmd/oslstats/run.go - follow this pattern
+11. When in plan mode, always use the interactive question tool if available
diff --git a/cmd/oslstats/httpserver.go b/cmd/oslstats/httpserver.go
index 8c0ff26..bd2763f 100644
--- a/cmd/oslstats/httpserver.go
+++ b/cmd/oslstats/httpserver.go
@@ -4,14 +4,15 @@ import (
 	"io/fs"
 	"net/http"
 
-	"git.haelnorr.com/h/golib/hws"
-	"git.haelnorr.com/h/oslstats/internal/config"
-	"git.haelnorr.com/h/oslstats/internal/handlers"
-	"git.haelnorr.com/h/oslstats/internal/session"
-
 	"git.haelnorr.com/h/golib/hlog"
+	"git.haelnorr.com/h/golib/hws"
 	"github.com/pkg/errors"
 	"github.com/uptrace/bun"
+
+	"git.haelnorr.com/h/oslstats/internal/config"
+	"git.haelnorr.com/h/oslstats/internal/discord"
+	"git.haelnorr.com/h/oslstats/internal/handlers"
+	"git.haelnorr.com/h/oslstats/internal/store"
 )
 
 func setupHttpServer(
@@ -19,7 +20,8 @@ func setupHttpServer(
 	config *config.Config,
 	logger *hlog.Logger,
 	bun *bun.DB,
-	store *session.Store,
+	store *store.Store,
+	discordAPI *discord.APIClient,
 ) (server *hws.Server, err error) {
 	if staticFS == nil {
 		return nil, errors.New("No filesystem provided")
@@ -55,7 +57,7 @@ func setupHttpServer(
 		return nil, errors.Wrap(err, "httpServer.LoggerIgnorePaths")
 	}
 
-	err = addRoutes(httpServer, &fs, config, bun, auth, store)
+	err = addRoutes(httpServer, &fs, config, bun, auth, store, discordAPI)
 	if err != nil {
 		return nil, errors.Wrap(err, "addRoutes")
 	}
diff --git a/cmd/oslstats/routes.go b/cmd/oslstats/routes.go
index e247234..e7161b7 100644
--- a/cmd/oslstats/routes.go
+++ b/cmd/oslstats/routes.go
@@ -5,13 +5,14 @@ import (
 
 	"git.haelnorr.com/h/golib/hws"
 	"git.haelnorr.com/h/golib/hwsauth"
-	"git.haelnorr.com/h/oslstats/internal/config"
-	"git.haelnorr.com/h/oslstats/internal/db"
-	"git.haelnorr.com/h/oslstats/internal/handlers"
-	"git.haelnorr.com/h/oslstats/internal/session"
-
 	"github.com/pkg/errors"
 	"github.com/uptrace/bun"
+
+	"git.haelnorr.com/h/oslstats/internal/config"
+	"git.haelnorr.com/h/oslstats/internal/db"
+	"git.haelnorr.com/h/oslstats/internal/discord"
+	"git.haelnorr.com/h/oslstats/internal/handlers"
+	"git.haelnorr.com/h/oslstats/internal/store"
 )
 
 func addRoutes(
@@ -20,7 +21,8 @@ func addRoutes(
 	cfg *config.Config,
 	conn *bun.DB,
 	auth *hwsauth.Authenticator[*db.User, bun.Tx],
-	store *session.Store,
+	store *store.Store,
+	discordAPI *discord.APIClient,
 ) error {
 	// Create the routes
 	routes := []hws.Route{
@@ -37,12 +39,12 @@ func addRoutes(
 		{
 			Path:    "/login",
 			Method:  hws.MethodGET,
-			Handler: auth.LogoutReq(handlers.Login(server, cfg)),
+			Handler: auth.LogoutReq(handlers.Login(server, cfg, store, discordAPI)),
 		},
 		{
 			Path:    "/auth/callback",
 			Method:  hws.MethodGET,
-			Handler: auth.LogoutReq(handlers.Callback(server, conn, cfg, store)),
+			Handler: auth.LogoutReq(handlers.Callback(server, conn, cfg, store, discordAPI)),
 		},
 		{
 			Path:    "/register",
diff --git a/cmd/oslstats/run.go b/cmd/oslstats/run.go
index 5dd1922..32395e8 100644
--- a/cmd/oslstats/run.go
+++ b/cmd/oslstats/run.go
@@ -9,10 +9,12 @@ import (
 	"time"
 
 	"git.haelnorr.com/h/golib/hlog"
-	"git.haelnorr.com/h/oslstats/internal/config"
-	"git.haelnorr.com/h/oslstats/internal/session"
-	"git.haelnorr.com/h/oslstats/pkg/embedfs"
 	"github.com/pkg/errors"
+
+	"git.haelnorr.com/h/oslstats/internal/config"
+	"git.haelnorr.com/h/oslstats/internal/discord"
+	"git.haelnorr.com/h/oslstats/internal/store"
+	"git.haelnorr.com/h/oslstats/pkg/embedfs"
 )
 
 // Initializes and runs the server
@@ -44,10 +46,14 @@ func run(ctx context.Context, w io.Writer, config *config.Config) error {
 
 	// Setup session store
 	logger.Debug().Msg("Setting up session store")
-	store := session.NewStore()
+	store := store.NewStore()
+
+	// Setup Discord API client
+	logger.Debug().Msg("Setting up Discord API client")
+	discordAPI := discord.NewRateLimitedClient(logger)
 
 	logger.Debug().Msg("Setting up HTTP server")
-	httpServer, err := setupHttpServer(&staticFS, config, logger, bun, store)
+	httpServer, err := setupHttpServer(&staticFS, config, logger, bun, store, discordAPI)
 	if err != nil {
 		return errors.Wrap(err, "setupHttpServer")
 	}
diff --git a/internal/discord/oauth.go b/internal/discord/oauth.go
index 73644ea..780a71b 100644
--- a/internal/discord/oauth.go
+++ b/internal/discord/oauth.go
@@ -43,7 +43,7 @@ func GetOAuthLink(cfg *Config, state, trustedHost string) (string, error) {
 	return fmt.Sprintf("%s?%s", oauthurl, values.Encode()), nil
 }
 
-func AuthorizeWithCode(cfg *Config, code, trustedHost string) (*Token, error) {
+func AuthorizeWithCode(cfg *Config, code, trustedHost string, apiClient *APIClient) (*Token, error) {
 	if code == "" {
 		return nil, errors.New("code cannot be empty")
 	}
@@ -53,6 +53,9 @@ func AuthorizeWithCode(cfg *Config, code, trustedHost string) (*Token, error) {
 	if trustedHost == "" {
 		return nil, errors.New("trustedHost cannot be empty")
 	}
+	if apiClient == nil {
+		return nil, errors.New("apiClient cannot be nil")
+	}
 	// Prepare form data
 	data := url.Values{}
 	data.Set("grant_type", "authorization_code")
@@ -72,9 +75,8 @@ func AuthorizeWithCode(cfg *Config, code, trustedHost string) (*Token, error) {
 
 	// Set basic auth (client_id and client_secret)
 	req.SetBasicAuth(cfg.ClientID, cfg.ClientSecret)
-	// Execute request
-	client := &http.Client{}
-	resp, err := client.Do(req)
+	// Execute request with rate limit handling
+	resp, err := apiClient.Do(req)
 	if err != nil {
 		return nil, errors.Wrap(err, "failed to execute request")
 	}
@@ -96,13 +98,16 @@ func AuthorizeWithCode(cfg *Config, code, trustedHost string) (*Token, error) {
 	return &tokenResp, nil
 }
 
-func RefreshToken(cfg *Config, token *Token) (*Token, error) {
+func RefreshToken(cfg *Config, token *Token, apiClient *APIClient) (*Token, error) {
 	if token == nil {
 		return nil, errors.New("token cannot be nil")
 	}
 	if cfg == nil {
 		return nil, errors.New("config cannot be nil")
 	}
+	if apiClient == nil {
+		return nil, errors.New("apiClient cannot be nil")
+	}
 	// Prepare form data
 	data := url.Values{}
 	data.Set("grant_type", "refresh_token")
@@ -121,9 +126,8 @@ func RefreshToken(cfg *Config, token *Token) (*Token, error) {
 
 	// Set basic auth (client_id and client_secret)
 	req.SetBasicAuth(cfg.ClientID, cfg.ClientSecret)
-	// Execute request
-	client := &http.Client{}
-	resp, err := client.Do(req)
+	// Execute request with rate limit handling
+	resp, err := apiClient.Do(req)
 	if err != nil {
 		return nil, errors.Wrap(err, "failed to execute request")
 	}
@@ -145,13 +149,16 @@ func RefreshToken(cfg *Config, token *Token) (*Token, error) {
 	return &tokenResp, nil
 }
 
-func RevokeToken(cfg *Config, token *Token) error {
+func RevokeToken(cfg *Config, token *Token, apiClient *APIClient) error {
 	if token == nil {
 		return errors.New("token cannot be nil")
 	}
 	if cfg == nil {
 		return errors.New("config cannot be nil")
 	}
+	if apiClient == nil {
+		return errors.New("apiClient cannot be nil")
+	}
 	// Prepare form data
 	data := url.Values{}
 	data.Set("token", token.AccessToken)
@@ -170,9 +177,8 @@ func RevokeToken(cfg *Config, token *Token) error {
 
 	// Set basic auth (client_id and client_secret)
 	req.SetBasicAuth(cfg.ClientID, cfg.ClientSecret)
-	// Execute request
-	client := &http.Client{}
-	resp, err := client.Do(req)
+	// Execute request with rate limit handling
+	resp, err := apiClient.Do(req)
 	if err != nil {
 		return errors.Wrap(err, "failed to execute request")
 	}
diff --git a/internal/discord/ratelimit.go b/internal/discord/ratelimit.go
new file mode 100644
index 0000000..4cde26d
--- /dev/null
+++ b/internal/discord/ratelimit.go
@@ -0,0 +1,235 @@
+package discord
+
+import (
+	"net"
+	"net/http"
+	"strconv"
+	"sync"
+	"time"
+
+	"git.haelnorr.com/h/golib/hlog"
+	"github.com/pkg/errors"
+)
+
+// RateLimitState tracks rate limit information for a specific bucket
+type RateLimitState struct {
+	Remaining int       // Requests remaining in current window
+	Limit     int       // Total requests allowed in window
+	Reset     time.Time // When the rate limit resets
+	Bucket    string    // Discord's bucket identifier
+}
+
+// APIClient is an HTTP client wrapper that handles Discord API rate limits
+type APIClient struct {
+	client  *http.Client
+	logger  *hlog.Logger
+	mu      sync.RWMutex
+	buckets map[string]*RateLimitState
+}
+
+// NewRateLimitedClient creates a new Discord API client with rate limit handling
+func NewRateLimitedClient(logger *hlog.Logger) *APIClient {
+	return &APIClient{
+		client:  &http.Client{Timeout: 30 * time.Second},
+		logger:  logger,
+		buckets: make(map[string]*RateLimitState),
+	}
+}
+
+// Do executes an HTTP request with automatic rate limit handling
+// It will wait if rate limits are about to be exceeded and retry once if a 429 is received
+func (c *APIClient) Do(req *http.Request) (*http.Response, error) {
+	if req == nil {
+		return nil, errors.New("request cannot be nil")
+	}
+
+	// Step 1: Check if we need to wait before making request
+	bucket := c.getBucketFromRequest(req)
+	if err := c.waitIfNeeded(bucket); err != nil {
+		return nil, err
+	}
+
+	// Step 2: Execute request
+	resp, err := c.client.Do(req)
+	if err != nil {
+		// Check if it's a network timeout
+		if netErr, ok := err.(net.Error); ok && netErr.Timeout() {
+			return nil, errors.Wrap(err, "request timed out")
+		}
+		return nil, errors.Wrap(err, "http request failed")
+	}
+
+	// Step 3: Update rate limit state from response headers
+	c.updateRateLimit(resp.Header)
+
+	// Step 4: Handle 429 (rate limited)
+	if resp.StatusCode == http.StatusTooManyRequests {
+		resp.Body.Close() // Close original response
+
+		retryAfter := c.parseRetryAfter(resp.Header)
+
+		// No Retry-After header, can't retry safely
+		if retryAfter == 0 {
+			c.logger.Warn().
+				Str("bucket", bucket).
+				Str("method", req.Method).
+				Str("path", req.URL.Path).
+				Msg("Rate limited but no Retry-After header provided")
+			return nil, errors.New("discord API rate limited but no Retry-After header provided")
+		}
+
+		// Retry-After exceeds 30 second cap
+		if retryAfter > 30*time.Second {
+			c.logger.Warn().
+				Str("bucket", bucket).
+				Str("method", req.Method).
+				Str("path", req.URL.Path).
+				Dur("retry_after", retryAfter).
+				Msg("Rate limited with Retry-After exceeding 30s cap, not retrying")
+			return nil, errors.Errorf(
+				"discord API rate limited (retry after %s exceeds 30s cap)",
+				retryAfter,
+			)
+		}
+
+		// Wait and retry
+		c.logger.Warn().
+			Str("bucket", bucket).
+			Str("method", req.Method).
+			Str("path", req.URL.Path).
+			Dur("retry_after", retryAfter).
+			Msg("Rate limited, waiting before retry")
+
+		time.Sleep(retryAfter)
+
+		// Retry the request
+		resp, err = c.client.Do(req)
+		if err != nil {
+			if netErr, ok := err.(net.Error); ok && netErr.Timeout() {
+				return nil, errors.Wrap(err, "retry request timed out")
+			}
+			return nil, errors.Wrap(err, "retry request failed")
+		}
+
+		// Update rate limit again after retry
+		c.updateRateLimit(resp.Header)
+
+		// If STILL rate limited after retry, return error
+		if resp.StatusCode == http.StatusTooManyRequests {
+			resp.Body.Close()
+			c.logger.Error().
+				Str("bucket", bucket).
+				Str("method", req.Method).
+				Str("path", req.URL.Path).
+				Msg("Still rate limited after retry, Discord may be experiencing issues")
+			return nil, errors.Errorf(
+				"discord API still rate limited after retry (waited %s), Discord may be experiencing issues",
+				retryAfter,
+			)
+		}
+	}
+
+	return resp, nil
+}
+
+// getBucketFromRequest extracts or generates bucket ID from request
+// For Discord, the bucket is typically METHOD:path until we get the actual bucket from headers
+func (c *APIClient) getBucketFromRequest(req *http.Request) string {
+	return req.Method + ":" + req.URL.Path
+}
+
+// waitIfNeeded checks if we need to delay before request to avoid hitting rate limits
+func (c *APIClient) waitIfNeeded(bucket string) error {
+	c.mu.RLock()
+	state, exists := c.buckets[bucket]
+	c.mu.RUnlock()
+
+	if !exists {
+		return nil // No state yet, proceed
+	}
+
+	now := time.Now()
+
+	// If we have no remaining requests and reset hasn't occurred, wait
+	if state.Remaining == 0 && now.Before(state.Reset) {
+		waitDuration := time.Until(state.Reset)
+		// Add small buffer (100ms) to ensure reset has occurred
+		waitDuration += 100 * time.Millisecond
+
+		if waitDuration > 0 {
+			c.logger.Debug().
+				Str("bucket", bucket).
+				Dur("wait_duration", waitDuration).
+				Msg("Proactively waiting for rate limit reset")
+			time.Sleep(waitDuration)
+		}
+	}
+
+	return nil
+}
+
+// updateRateLimit parses response headers and updates bucket state
+func (c *APIClient) updateRateLimit(headers http.Header) {
+	bucket := headers.Get("X-RateLimit-Bucket")
+	if bucket == "" {
+		return // No bucket info, can't track
+	}
+
+	// Parse headers
+	limit := c.parseInt(headers.Get("X-RateLimit-Limit"))
+	remaining := c.parseInt(headers.Get("X-RateLimit-Remaining"))
+	resetAfter := c.parseFloat(headers.Get("X-RateLimit-Reset-After"))
+
+	state := &RateLimitState{
+		Bucket:    bucket,
+		Limit:     limit,
+		Remaining: remaining,
+		Reset:     time.Now().Add(time.Duration(resetAfter * float64(time.Second))),
+	}
+
+	c.mu.Lock()
+	c.buckets[bucket] = state
+	c.mu.Unlock()
+
+	// Log rate limit state for debugging
+	c.logger.Debug().
+		Str("bucket", bucket).
+		Int("remaining", remaining).
+		Int("limit", limit).
+		Dur("reset_in", time.Until(state.Reset)).
+		Msg("Rate limit state updated")
+}
+
+// parseRetryAfter extracts retry delay from Retry-After header
+func (c *APIClient) parseRetryAfter(headers http.Header) time.Duration {
+	retryAfter := headers.Get("Retry-After")
+	if retryAfter == "" {
+		return 0
+	}
+
+	// Discord returns seconds as float
+	seconds := c.parseFloat(retryAfter)
+	if seconds <= 0 {
+		return 0
+	}
+
+	return time.Duration(seconds * float64(time.Second))
+}
+
+// parseInt parses an integer from a header value, returns 0 on error
+func (c *APIClient) parseInt(s string) int {
+	if s == "" {
+		return 0
+	}
+	i, _ := strconv.Atoi(s)
+	return i
+}
+
+// parseFloat parses a float from a header value, returns 0 on error
+func (c *APIClient) parseFloat(s string) float64 {
+	if s == "" {
+		return 0
+	}
+	f, _ := strconv.ParseFloat(s, 64)
+	return f
+}
diff --git a/internal/discord/ratelimit_test.go b/internal/discord/ratelimit_test.go
new file mode 100644
index 0000000..33f6b57
--- /dev/null
+++ b/internal/discord/ratelimit_test.go
@@ -0,0 +1,459 @@
+package discord
+
+import (
+	"encoding/json"
+	"io"
+	"net/http"
+	"net/http/httptest"
+	"strings"
+	"sync"
+	"testing"
+	"time"
+
+	"git.haelnorr.com/h/golib/hlog"
+)
+
+// testLogger creates a test logger for testing
+func testLogger(t *testing.T) *hlog.Logger {
+	level, _ := hlog.LogLevel("debug")
+	cfg := &hlog.Config{
+		LogLevel:  level,
+		LogOutput: "console",
+	}
+	logger, err := hlog.NewLogger(cfg, io.Discard)
+	if err != nil {
+		t.Fatalf("failed to create test logger: %v", err)
+	}
+	return logger
+}
+
+func TestNewRateLimitedClient(t *testing.T) {
+	logger := testLogger(t)
+	client := NewRateLimitedClient(logger)
+
+	if client == nil {
+		t.Fatal("NewRateLimitedClient returned nil")
+	}
+	if client.client == nil {
+		t.Error("client.client is nil")
+	}
+	if client.logger == nil {
+		t.Error("client.logger is nil")
+	}
+	if client.buckets == nil {
+		t.Error("client.buckets map is nil")
+	}
+}
+
+func TestAPIClient_Do_Success(t *testing.T) {
+	logger := testLogger(t)
+	client := NewRateLimitedClient(logger)
+
+	// Mock server that returns success with rate limit headers
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.Header().Set("X-RateLimit-Bucket", "test-bucket")
+		w.Header().Set("X-RateLimit-Limit", "5")
+		w.Header().Set("X-RateLimit-Remaining", "3")
+		w.Header().Set("X-RateLimit-Reset-After", "2.5")
+		w.WriteHeader(http.StatusOK)
+		json.NewEncoder(w).Encode(map[string]string{"status": "ok"})
+	}))
+	defer server.Close()
+
+	req, err := http.NewRequest("GET", server.URL+"/test", nil)
+	if err != nil {
+		t.Fatalf("failed to create request: %v", err)
+	}
+
+	resp, err := client.Do(req)
+	if err != nil {
+		t.Fatalf("Do() returned error: %v", err)
+	}
+	defer resp.Body.Close()
+
+	if resp.StatusCode != http.StatusOK {
+		t.Errorf("expected status 200, got %d", resp.StatusCode)
+	}
+
+	// Check that rate limit state was updated
+	client.mu.RLock()
+	state, exists := client.buckets["test-bucket"]
+	client.mu.RUnlock()
+
+	if !exists {
+		t.Fatal("rate limit state not stored")
+	}
+	if state.Remaining != 3 {
+		t.Errorf("expected remaining=3, got %d", state.Remaining)
+	}
+	if state.Limit != 5 {
+		t.Errorf("expected limit=5, got %d", state.Limit)
+	}
+}
+
+func TestAPIClient_Do_RateLimitRetrySuccess(t *testing.T) {
+	logger := testLogger(t)
+	client := NewRateLimitedClient(logger)
+
+	attemptCount := 0
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		attemptCount++
+		if attemptCount == 1 {
+			// First request: return 429
+			w.Header().Set("X-RateLimit-Bucket", "test-bucket")
+			w.Header().Set("Retry-After", "0.1") // 100ms
+			w.WriteHeader(http.StatusTooManyRequests)
+			json.NewEncoder(w).Encode(map[string]string{
+				"error":             "rate_limited",
+				"error_description": "You are being rate limited",
+			})
+			return
+		}
+		// Second request: success
+		w.Header().Set("X-RateLimit-Bucket", "test-bucket")
+		w.Header().Set("X-RateLimit-Limit", "5")
+		w.Header().Set("X-RateLimit-Remaining", "4")
+		w.Header().Set("X-RateLimit-Reset-After", "2.5")
+		w.WriteHeader(http.StatusOK)
+		json.NewEncoder(w).Encode(map[string]string{"status": "ok"})
+	}))
+	defer server.Close()
+
+	req, err := http.NewRequest("POST", server.URL+"/oauth2/token", nil)
+	if err != nil {
+		t.Fatalf("failed to create request: %v", err)
+	}
+
+	start := time.Now()
+	resp, err := client.Do(req)
+	elapsed := time.Since(start)
+
+	if err != nil {
+		t.Fatalf("Do() returned error: %v", err)
+	}
+	defer resp.Body.Close()
+
+	if resp.StatusCode != http.StatusOK {
+		t.Errorf("expected status 200 after retry, got %d", resp.StatusCode)
+	}
+
+	if attemptCount != 2 {
+		t.Errorf("expected 2 attempts (initial + retry), got %d", attemptCount)
+	}
+
+	// Should have waited approximately 100ms
+	if elapsed < 100*time.Millisecond {
+		t.Errorf("expected delay of ~100ms, but took %v", elapsed)
+	}
+}
+
+func TestAPIClient_Do_RateLimitRetryFails(t *testing.T) {
+	logger := testLogger(t)
+	client := NewRateLimitedClient(logger)
+
+	attemptCount := 0
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		attemptCount++
+		// Always return 429
+		w.Header().Set("X-RateLimit-Bucket", "test-bucket")
+		w.Header().Set("Retry-After", "0.05") // 50ms
+		w.WriteHeader(http.StatusTooManyRequests)
+		json.NewEncoder(w).Encode(map[string]string{
+			"error": "rate_limited",
+		})
+	}))
+	defer server.Close()
+
+	req, err := http.NewRequest("POST", server.URL+"/oauth2/token", nil)
+	if err != nil {
+		t.Fatalf("failed to create request: %v", err)
+	}
+
+	resp, err := client.Do(req)
+
+	if err == nil {
+		resp.Body.Close()
+		t.Fatal("Do() should have returned error after failed retry")
+	}
+
+	if !strings.Contains(err.Error(), "still rate limited after retry") {
+		t.Errorf("expected 'still rate limited after retry' error, got: %v", err)
+	}
+
+	if attemptCount != 2 {
+		t.Errorf("expected 2 attempts, got %d", attemptCount)
+	}
+}
+
+func TestAPIClient_Do_RateLimitTooLong(t *testing.T) {
+	logger := testLogger(t)
+	client := NewRateLimitedClient(logger)
+
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.Header().Set("Retry-After", "60") // 60 seconds > 30s cap
+		w.WriteHeader(http.StatusTooManyRequests)
+		json.NewEncoder(w).Encode(map[string]string{
+			"error": "rate_limited",
+		})
+	}))
+	defer server.Close()
+
+	req, err := http.NewRequest("POST", server.URL+"/oauth2/token", nil)
+	if err != nil {
+		t.Fatalf("failed to create request: %v", err)
+	}
+
+	start := time.Now()
+	resp, err := client.Do(req)
+	elapsed := time.Since(start)
+
+	if err == nil {
+		resp.Body.Close()
+		t.Fatal("Do() should have returned error for Retry-After > 30s")
+	}
+
+	if !strings.Contains(err.Error(), "exceeds 30s cap") {
+		t.Errorf("expected 'exceeds 30s cap' error, got: %v", err)
+	}
+
+	// Should NOT have waited (immediate error)
+	if elapsed > 1*time.Second {
+		t.Errorf("should return immediately, but took %v", elapsed)
+	}
+}
+
+func TestAPIClient_Do_NoRetryAfterHeader(t *testing.T) {
+	logger := testLogger(t)
+	client := NewRateLimitedClient(logger)
+
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		// Return 429 but NO Retry-After header
+		w.WriteHeader(http.StatusTooManyRequests)
+		json.NewEncoder(w).Encode(map[string]string{
+			"error": "rate_limited",
+		})
+	}))
+	defer server.Close()
+
+	req, err := http.NewRequest("POST", server.URL+"/oauth2/token", nil)
+	if err != nil {
+		t.Fatalf("failed to create request: %v", err)
+	}
+
+	resp, err := client.Do(req)
+
+	if err == nil {
+		resp.Body.Close()
+		t.Fatal("Do() should have returned error when no Retry-After header")
+	}
+
+	if !strings.Contains(err.Error(), "no Retry-After header") {
+		t.Errorf("expected 'no Retry-After header' error, got: %v", err)
+	}
+}
+
+func TestAPIClient_UpdateRateLimit(t *testing.T) {
+	logger := testLogger(t)
+	client := NewRateLimitedClient(logger)
+
+	headers := http.Header{}
+	headers.Set("X-RateLimit-Bucket", "global")
+	headers.Set("X-RateLimit-Limit", "10")
+	headers.Set("X-RateLimit-Remaining", "7")
+	headers.Set("X-RateLimit-Reset-After", "5.5")
+
+	client.updateRateLimit(headers)
+
+	client.mu.RLock()
+	state, exists := client.buckets["global"]
+	client.mu.RUnlock()
+
+	if !exists {
+		t.Fatal("bucket state not created")
+	}
+
+	if state.Bucket != "global" {
+		t.Errorf("expected bucket='global', got '%s'", state.Bucket)
+	}
+	if state.Limit != 10 {
+		t.Errorf("expected limit=10, got %d", state.Limit)
+	}
+	if state.Remaining != 7 {
+		t.Errorf("expected remaining=7, got %d", state.Remaining)
+	}
+
+	// Check reset time is approximately 5.5 seconds from now
+	resetIn := time.Until(state.Reset)
+	if resetIn < 5*time.Second || resetIn > 6*time.Second {
+		t.Errorf("expected reset in ~5.5s, got %v", resetIn)
+	}
+}
+
+func TestAPIClient_WaitIfNeeded(t *testing.T) {
+	logger := testLogger(t)
+	client := NewRateLimitedClient(logger)
+
+	// Set up a bucket with 0 remaining and reset in future
+	bucket := "test-bucket"
+	client.mu.Lock()
+	client.buckets[bucket] = &RateLimitState{
+		Bucket:    bucket,
+		Limit:     5,
+		Remaining: 0,
+		Reset:     time.Now().Add(200 * time.Millisecond),
+	}
+	client.mu.Unlock()
+
+	start := time.Now()
+	err := client.waitIfNeeded(bucket)
+	elapsed := time.Since(start)
+
+	if err != nil {
+		t.Errorf("waitIfNeeded returned error: %v", err)
+	}
+
+	// Should have waited ~200ms + 100ms buffer
+	if elapsed < 200*time.Millisecond {
+		t.Errorf("expected wait of ~300ms, but took %v", elapsed)
+	}
+	if elapsed > 500*time.Millisecond {
+		t.Errorf("waited too long: %v", elapsed)
+	}
+}
+
+func TestAPIClient_WaitIfNeeded_NoWait(t *testing.T) {
+	logger := testLogger(t)
+	client := NewRateLimitedClient(logger)
+
+	// Set up a bucket with remaining requests
+	bucket := "test-bucket"
+	client.mu.Lock()
+	client.buckets[bucket] = &RateLimitState{
+		Bucket:    bucket,
+		Limit:     5,
+		Remaining: 3,
+		Reset:     time.Now().Add(5 * time.Second),
+	}
+	client.mu.Unlock()
+
+	start := time.Now()
+	err := client.waitIfNeeded(bucket)
+	elapsed := time.Since(start)
+
+	if err != nil {
+		t.Errorf("waitIfNeeded returned error: %v", err)
+	}
+
+	// Should NOT wait (has remaining requests)
+	if elapsed > 10*time.Millisecond {
+		t.Errorf("should not wait when remaining > 0, but took %v", elapsed)
+	}
+}
+
+func TestAPIClient_Do_Concurrent(t *testing.T) {
+	logger := testLogger(t)
+	client := NewRateLimitedClient(logger)
+
+	requestCount := 0
+	var mu sync.Mutex
+
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		mu.Lock()
+		requestCount++
+		count := requestCount
+		mu.Unlock()
+
+		w.Header().Set("X-RateLimit-Bucket", "concurrent-bucket")
+		w.Header().Set("X-RateLimit-Limit", "10")
+		w.Header().Set("X-RateLimit-Remaining", "5")
+		w.Header().Set("X-RateLimit-Reset-After", "1.0")
+		w.WriteHeader(http.StatusOK)
+		json.NewEncoder(w).Encode(map[string]string{"count": string(rune(count))})
+	}))
+	defer server.Close()
+
+	// Launch 10 concurrent requests
+	var wg sync.WaitGroup
+	errors := make(chan error, 10)
+
+	for i := 0; i < 10; i++ {
+		wg.Add(1)
+		go func() {
+			defer wg.Done()
+
+			req, err := http.NewRequest("GET", server.URL+"/test", nil)
+			if err != nil {
+				errors <- err
+				return
+			}
+
+			resp, err := client.Do(req)
+			if err != nil {
+				errors <- err
+				return
+			}
+			resp.Body.Close()
+		}()
+	}
+
+	wg.Wait()
+	close(errors)
+
+	// Check for any errors
+	for err := range errors {
+		t.Errorf("concurrent request failed: %v", err)
+	}
+
+	// All requests should have completed
+	mu.Lock()
+	finalCount := requestCount
+	mu.Unlock()
+
+	if finalCount != 10 {
+		t.Errorf("expected 10 requests, got %d", finalCount)
+	}
+
+	// Check rate limit state is consistent (no data races)
+	client.mu.RLock()
+	state, exists := client.buckets["concurrent-bucket"]
+	client.mu.RUnlock()
+
+	if !exists {
+		t.Fatal("bucket state not found after concurrent requests")
+	}
+
+	// State should exist and be valid
+	if state.Limit != 10 {
+		t.Errorf("expected limit=10, got %d (possible race condition)", state.Limit)
+	}
+}
+
+func TestAPIClient_ParseRetryAfter(t *testing.T) {
+	logger := testLogger(t)
+	client := NewRateLimitedClient(logger)
+
+	tests := []struct {
+		name     string
+		header   string
+		expected time.Duration
+	}{
+		{"integer seconds", "2", 2 * time.Second},
+		{"float seconds", "2.5", 2500 * time.Millisecond},
+		{"zero", "0", 0},
+		{"empty", "", 0},
+		{"invalid", "abc", 0},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			headers := http.Header{}
+			headers.Set("Retry-After", tt.header)
+
+			result := client.parseRetryAfter(headers)
+
+			if result != tt.expected {
+				t.Errorf("expected %v, got %v", tt.expected, result)
+			}
+		})
+	}
+}
diff --git a/internal/handlers/callback.go b/internal/handlers/callback.go
index d0677aa..47239c5 100644
--- a/internal/handlers/callback.go
+++ b/internal/handlers/callback.go
@@ -6,18 +6,49 @@ import (
 	"time"
 
 	"git.haelnorr.com/h/golib/hws"
+	"github.com/pkg/errors"
+	"github.com/uptrace/bun"
+
 	"git.haelnorr.com/h/oslstats/internal/config"
 	"git.haelnorr.com/h/oslstats/internal/db"
 	"git.haelnorr.com/h/oslstats/internal/discord"
-	"git.haelnorr.com/h/oslstats/internal/session"
+	"git.haelnorr.com/h/oslstats/internal/store"
 	"git.haelnorr.com/h/oslstats/pkg/oauth"
-	"github.com/pkg/errors"
-	"github.com/uptrace/bun"
 )
 
-func Callback(server *hws.Server, conn *bun.DB, cfg *config.Config, store *session.Store) http.Handler {
+func Callback(server *hws.Server, conn *bun.DB, cfg *config.Config, store *store.Store, discordAPI *discord.APIClient) http.Handler {
 	return http.HandlerFunc(
 		func(w http.ResponseWriter, r *http.Request) {
+			// Track callback redirect attempts
+			attempts, exceeded, track := store.TrackRedirect(r, "/callback", 5)
+
+			if exceeded {
+				// Build detailed error for logging
+				err := errors.Errorf(
+					"callback redirect loop detected after %d attempts | ip=%s ua=%s path=%s first_seen=%s",
+					attempts,
+					track.IP,
+					track.UserAgent,
+					track.Path,
+					track.FirstSeen.Format("2006-01-02T15:04:05Z07:00"),
+				)
+
+				// Clear the tracking entry
+				store.ClearRedirectTrack(r, "/callback")
+
+				// Show error page
+				throwError(
+					server,
+					w,
+					r,
+					http.StatusBadRequest,
+					"OAuth callback failed: Too many redirect attempts. Please try logging in again.",
+					err,
+					"warn",
+				)
+				return
+			}
+
 			state := r.URL.Query().Get("state")
 			code := r.URL.Query().Get("code")
 			if state == "" && code == "" {
@@ -41,6 +72,10 @@ func Callback(server *hws.Server, conn *bun.DB, cfg *config.Config, store *sessi
 				}
 				return
 			}
+			// SUCCESS POINT: State verified successfully
+			// Clear redirect tracking - OAuth callback completed successfully
+			store.ClearRedirectTrack(r, "/callback")
+
 			switch data {
 			case "login":
 				ctx, cancel := context.WithTimeout(r.Context(), 10*time.Second)
@@ -51,7 +86,7 @@ func Callback(server *hws.Server, conn *bun.DB, cfg *config.Config, store *sessi
 					return
 				}
 				defer tx.Rollback()
-				redirect, err := login(ctx, tx, cfg, w, r, code, store)
+				redirect, err := login(ctx, tx, cfg, w, r, code, store, discordAPI)
 				if err != nil {
 					throwInternalServiceError(server, w, r, "OAuth login failed", err)
 					return
@@ -122,9 +157,10 @@ func login(
 	w http.ResponseWriter,
 	r *http.Request,
 	code string,
-	store *session.Store,
+	store *store.Store,
+	discordAPI *discord.APIClient,
 ) (func(), error) {
-	token, err := discord.AuthorizeWithCode(cfg.Discord, code, cfg.HWSAuth.TrustedHost)
+	token, err := discord.AuthorizeWithCode(cfg.Discord, code, cfg.HWSAuth.TrustedHost, discordAPI)
 	if err != nil {
 		return nil, errors.Wrap(err, "discord.AuthorizeWithCode")
 	}
diff --git a/internal/handlers/login.go b/internal/handlers/login.go
index 3ff126f..e46312a 100644
--- a/internal/handlers/login.go
+++ b/internal/handlers/login.go
@@ -4,14 +4,47 @@ import (
 	"net/http"
 
 	"git.haelnorr.com/h/golib/hws"
+	"github.com/pkg/errors"
+
 	"git.haelnorr.com/h/oslstats/internal/config"
 	"git.haelnorr.com/h/oslstats/internal/discord"
+	"git.haelnorr.com/h/oslstats/internal/store"
 	"git.haelnorr.com/h/oslstats/pkg/oauth"
 )
 
-func Login(server *hws.Server, cfg *config.Config) http.Handler {
+func Login(server *hws.Server, cfg *config.Config, st *store.Store, discordAPI *discord.APIClient) http.Handler {
 	return http.HandlerFunc(
 		func(w http.ResponseWriter, r *http.Request) {
+			// Track login redirect attempts
+			attempts, exceeded, track := st.TrackRedirect(r, "/login", 5)
+
+			if exceeded {
+				// Build detailed error for logging
+				err := errors.Errorf(
+					"login redirect loop detected after %d attempts | ip=%s ua=%s path=%s first_seen=%s",
+					attempts,
+					track.IP,
+					track.UserAgent,
+					track.Path,
+					track.FirstSeen.Format("2006-01-02T15:04:05Z07:00"),
+				)
+
+				// Clear the tracking entry
+				st.ClearRedirectTrack(r, "/login")
+
+				// Show error page
+				throwError(
+					server,
+					w,
+					r,
+					http.StatusBadRequest,
+					"Login failed: Too many redirect attempts. Please clear your browser cookies and try again.",
+					err,
+					"warn",
+				)
+				return
+			}
+
 			state, uak, err := oauth.GenerateState(cfg.OAuth, "login")
 			if err != nil {
 				throwInternalServiceError(server, w, r, "Failed to generate state token", err)
@@ -24,6 +57,11 @@ func Login(server *hws.Server, cfg *config.Config) http.Handler {
 				throwInternalServiceError(server, w, r, "An error occurred trying to generate the login link", err)
 				return
 			}
+
+			// SUCCESS POINT: OAuth link generated, redirecting to Discord
+			// Clear redirect tracking - user successfully initiated OAuth
+			st.ClearRedirectTrack(r, "/login")
+
 			http.Redirect(w, r, link, http.StatusSeeOther)
 		},
 	)
diff --git a/internal/handlers/register.go b/internal/handlers/register.go
index b871e45..d70691f 100644
--- a/internal/handlers/register.go
+++ b/internal/handlers/register.go
@@ -6,31 +6,63 @@ import (
 	"time"
 
 	"git.haelnorr.com/h/golib/hws"
+	"github.com/pkg/errors"
+	"github.com/uptrace/bun"
+
 	"git.haelnorr.com/h/oslstats/internal/config"
 	"git.haelnorr.com/h/oslstats/internal/db"
-	"git.haelnorr.com/h/oslstats/internal/session"
+	"git.haelnorr.com/h/oslstats/internal/store"
 	"git.haelnorr.com/h/oslstats/internal/view/page"
-	"github.com/uptrace/bun"
 )
 
 func Register(
 	server *hws.Server,
 	conn *bun.DB,
 	cfg *config.Config,
-	store *session.Store,
+	store *store.Store,
 ) http.Handler {
 	return http.HandlerFunc(
 		func(w http.ResponseWriter, r *http.Request) {
+			attempts, exceeded, track := store.TrackRedirect(r, "/register", 3)
+
+			if exceeded {
+				err := errors.Errorf(
+					"registration redirect loop detected after %d attempts | ip=%s ua=%s path=%s first_seen=%s ssl=%t",
+					attempts,
+					track.IP,
+					track.UserAgent,
+					track.Path,
+					track.FirstSeen.Format("2006-01-02T15:04:05Z07:00"),
+					cfg.HWSAuth.SSL,
+				)
+
+				store.ClearRedirectTrack(r, "/register")
+
+				throwError(
+					server,
+					w,
+					r,
+					http.StatusBadRequest,
+					"Registration failed: Cookies appear to be blocked or disabled. Please enable cookies in your browser and try again. If this problem persists, try a different browser or contact support.",
+					err,
+					"warn",
+				)
+				return
+			}
+
 			sessionCookie, err := r.Cookie("registration_session")
 			if err != nil {
 				http.Redirect(w, r, "/login", http.StatusSeeOther)
 				return
 			}
 			details, ok := store.GetRegistrationSession(sessionCookie.Value)
+			ok = false
 			if !ok {
 				http.Redirect(w, r, "/login", http.StatusSeeOther)
 				return
 			}
+
+			store.ClearRedirectTrack(r, "/register")
 			ctx, cancel := context.WithTimeout(r.Context(), 10*time.Second)
 			defer cancel()
 			tx, err := conn.BeginTx(ctx, nil)
@@ -65,12 +97,11 @@ func IsUsernameUnique(
 	server *hws.Server,
 	conn *bun.DB,
 	cfg *config.Config,
-	store *session.Store,
+	store *store.Store,
 ) http.Handler {
 	return http.HandlerFunc(
 		func(w http.ResponseWriter, r *http.Request) {
 			username := r.FormValue("username")
-			// check if its unique
 			ctx, cancel := context.WithTimeout(r.Context(), 10*time.Second)
 			defer cancel()
 			tx, err := conn.BeginTx(ctx, nil)
diff --git a/internal/session/store.go b/internal/session/store.go
deleted file mode 100644
index fe77e62..0000000
--- a/internal/session/store.go
+++ /dev/null
@@ -1,46 +0,0 @@
-package session
-
-import (
-	"crypto/rand"
-	"encoding/base64"
-	"sync"
-	"time"
-)
-
-type Store struct {
-	sessions sync.Map
-	cleanup  *time.Ticker
-}
-
-func NewStore() *Store {
-	s := &Store{
-		cleanup: time.NewTicker(1 * time.Minute),
-	}
-
-	// Background cleanup of expired sessions
-	go func() {
-		for range s.cleanup.C {
-			s.cleanupExpired()
-		}
-	}()
-
-	return s
-}
-
-func (s *Store) Delete(id string) {
-	s.sessions.Delete(id)
-}
-func (s *Store) cleanupExpired() {
-	s.sessions.Range(func(key, value any) bool {
-		session := value.(*RegistrationSession)
-		if time.Now().After(session.ExpiresAt) {
-			s.sessions.Delete(key)
-		}
-		return true
-	})
-}
-func generateID() string {
-	b := make([]byte, 32)
-	rand.Read(b)
-	return base64.RawURLEncoding.EncodeToString(b)
-}
diff --git a/internal/session/newlogin.go b/internal/store/newlogin.go
similarity index 98%
rename from internal/session/newlogin.go
rename to internal/store/newlogin.go
index d1c60ba..0e62529 100644
--- a/internal/session/newlogin.go
+++ b/internal/store/newlogin.go
@@ -1,4 +1,4 @@
-package session
+package store
 
 import (
 	"errors"
diff --git a/internal/store/redirects.go b/internal/store/redirects.go
new file mode 100644
index 0000000..e2e7852
--- /dev/null
+++ b/internal/store/redirects.go
@@ -0,0 +1,95 @@
+package store
+
+import (
+	"net"
+	"net/http"
+	"strings"
+	"time"
+)
+
+// getClientIP extracts the client IP address, checking X-Forwarded-For first
+func getClientIP(r *http.Request) string {
+	// Check X-Forwarded-For header (comma-separated list, first is client)
+	if xff := r.Header.Get("X-Forwarded-For"); xff != "" {
+		// Take the first IP in the list
+		ips := strings.Split(xff, ",")
+		if len(ips) > 0 {
+			return strings.TrimSpace(ips[0])
+		}
+	}
+
+	// Fall back to RemoteAddr (format: "IP:port" or "[IPv6]:port")
+	// Use net.SplitHostPort to properly handle both IPv4 and IPv6
+	host, _, err := net.SplitHostPort(r.RemoteAddr)
+	if err != nil {
+		// If SplitHostPort fails, return as-is (shouldn't happen with valid RemoteAddr)
+		return r.RemoteAddr
+	}
+	return host
+}
+
+// TrackRedirect increments the redirect counter for this IP+UA+Path combination
+// Returns the current attempt count, whether limit was exceeded, and the track details
+func (s *Store) TrackRedirect(r *http.Request, path string, maxAttempts int) (attempts int, exceeded bool, track *RedirectTrack) {
+	if r == nil {
+		return 0, false, nil
+	}
+
+	ip := getClientIP(r)
+	userAgent := r.UserAgent()
+	key := redirectKey(ip, userAgent, path)
+
+	now := time.Now()
+	expiresAt := now.Add(5 * time.Minute)
+
+	// Try to load existing track
+	val, exists := s.redirectTracks.Load(key)
+	if exists {
+		track = val.(*RedirectTrack)
+
+		// Check if expired
+		if now.After(track.ExpiresAt) {
+			// Expired, start fresh
+			track = &RedirectTrack{
+				IP:        ip,
+				UserAgent: userAgent,
+				Path:      path,
+				Attempts:  1,
+				FirstSeen: now,
+				ExpiresAt: expiresAt,
+			}
+			s.redirectTracks.Store(key, track)
+			return 1, false, track
+		}
+
+		// Increment existing
+		track.Attempts++
+		track.ExpiresAt = expiresAt // Extend expiry
+		exceeded = track.Attempts >= maxAttempts
+		return track.Attempts, exceeded, track
+	}
+
+	// Create new track
+	track = &RedirectTrack{
+		IP:        ip,
+		UserAgent: userAgent,
+		Path:      path,
+		Attempts:  1,
+		FirstSeen: now,
+		ExpiresAt: expiresAt,
+	}
+	s.redirectTracks.Store(key, track)
+	return 1, false, track
+}
+
+// ClearRedirectTrack removes a redirect tracking entry (called after successful completion)
+func (s *Store) ClearRedirectTrack(r *http.Request, path string) {
+	if r == nil {
+		return
+	}
+
+	ip := getClientIP(r)
+	userAgent := r.UserAgent()
+	key := redirectKey(ip, userAgent, path)
+	s.redirectTracks.Delete(key)
+}
diff --git a/internal/store/store.go b/internal/store/store.go
new file mode 100644
index 0000000..5620e58
--- /dev/null
+++ b/internal/store/store.go
@@ -0,0 +1,80 @@
+package store
+
+import (
+	"crypto/rand"
+	"encoding/base64"
+	"fmt"
+	"sync"
+	"time"
+)
+
+// RedirectTrack represents a single redirect attempt tracking entry
+type RedirectTrack struct {
+	IP        string    // Client IP (X-Forwarded-For aware)
+	UserAgent string    // Full User-Agent string for debugging
+	Path      string    // Request path (without query params)
+	Attempts  int       // Number of redirect attempts
+	FirstSeen time.Time // When first redirect was tracked
+	ExpiresAt time.Time // When to clean up this entry
+}
+
+type Store struct {
+	sessions       sync.Map // key: string, value: *RegistrationSession
+	redirectTracks sync.Map // key: string, value: *RedirectTrack
+	cleanup        *time.Ticker
+}
+
+func NewStore() *Store {
+	s := &Store{
+		cleanup: time.NewTicker(1 * time.Minute),
+	}
+
+	// Background cleanup of expired sessions
+	go func() {
+		for range s.cleanup.C {
+			s.cleanupExpired()
+		}
+	}()
+
+	return s
+}
+
+func (s *Store) Delete(id string) {
+	s.sessions.Delete(id)
+}
+func (s *Store) cleanupExpired() {
+	now := time.Now()
+
+	// Clean up expired registration sessions
+	s.sessions.Range(func(key, value any) bool {
+		session := value.(*RegistrationSession)
+		if now.After(session.ExpiresAt) {
+			s.sessions.Delete(key)
+		}
+		return true
+	})
+
+	// Clean up expired redirect tracks
+	s.redirectTracks.Range(func(key, value any) bool {
+		track := value.(*RedirectTrack)
+		if now.After(track.ExpiresAt) {
+			s.redirectTracks.Delete(key)
+		}
+		return true
+	})
+}
+func generateID() string {
+	b := make([]byte, 32)
+	rand.Read(b)
+	return base64.RawURLEncoding.EncodeToString(b)
+}
+
+// redirectKey generates a unique key for tracking redirects
+// Uses IP + first 100 chars of UA + path as key (not hashed for debugging)
+func redirectKey(ip, userAgent, path string) string {
+	ua := userAgent
+	if len(ua) > 100 {
+		ua = ua[:100]
+	}
+	return fmt.Sprintf("%s:%s:%s", ip, ua, path)
+}
diff --git a/pkg/embedfs/files/css/output.css b/pkg/embedfs/files/css/output.css
index 022341c..0643362 100644
--- a/pkg/embedfs/files/css/output.css
+++ b/pkg/embedfs/files/css/output.css
@@ -232,18 +232,12 @@
   .top-0 {
     top: calc(var(--spacing) * 0);
   }
-  .top-2 {
-    top: calc(var(--spacing) * 2);
-  }
   .top-4 {
     top: calc(var(--spacing) * 4);
   }
   .right-0 {
     right: calc(var(--spacing) * 0);
   }
-  .right-2 {
-    right: calc(var(--spacing) * 2);
-  }
   .bottom-0 {
     bottom: calc(var(--spacing) * 0);
   }
@@ -253,18 +247,9 @@
   .z-10 {
     z-index: 10;
   }
-  .float-left {
-    float: left;
-  }
-  .m-0 {
-    margin: calc(var(--spacing) * 0);
-  }
   .mx-auto {
     margin-inline: auto;
   }
-  .mt-1 {
-    margin-top: calc(var(--spacing) * 1);
-  }
   .mt-1\.5 {
     margin-top: calc(var(--spacing) * 1.5);
   }
@@ -298,21 +283,12 @@
   .mt-24 {
     margin-top: calc(var(--spacing) * 24);
   }
-  .mr-0 {
-    margin-right: calc(var(--spacing) * 0);
-  }
-  .mr-2 {
-    margin-right: calc(var(--spacing) * 2);
-  }
   .mr-5 {
     margin-right: calc(var(--spacing) * 5);
   }
   .mb-auto {
     margin-bottom: auto;
   }
-  .ml-0 {
-    margin-left: calc(var(--spacing) * 0);
-  }
   .ml-2 {
     margin-left: calc(var(--spacing) * 2);
   }
@@ -322,9 +298,6 @@
   .block {
     display: block;
   }
-  .contents {
-    display: contents;
-  }
   .flex {
     display: flex;
   }
@@ -343,9 +316,6 @@
   .inline-flex {
     display: inline-flex;
   }
-  .table {
-    display: table;
-  }
   .size-5 {
     width: calc(var(--spacing) * 5);
     height: calc(var(--spacing) * 5);
@@ -396,9 +366,6 @@
   .flex-1 {
     flex: 1;
   }
-  .border-collapse {
-    border-collapse: collapse;
-  }
   .translate-x-0 {
     --tw-translate-x: calc(var(--spacing) * 0);
     translate: var(--tw-translate-x) var(--tw-translate-y);
@@ -413,9 +380,6 @@
   .cursor-pointer {
     cursor: pointer;
   }
-  .resize {
-    resize: both;
-  }
   .flex-col {
     flex-direction: column;
   }
@@ -670,9 +634,6 @@
   .text-text {
     color: var(--text);
   }
-  .underline {
-    text-decoration-line: underline;
-  }
   .opacity-0 {
     opacity: 0%;
   }
@@ -687,10 +648,6 @@
     --tw-shadow: 0 1px 3px 0 var(--tw-shadow-color, rgb(0 0 0 / 0.1)), 0 1px 2px -1px var(--tw-shadow-color, rgb(0 0 0 / 0.1));
     box-shadow: var(--tw-inset-shadow), var(--tw-inset-ring-shadow), var(--tw-ring-offset-shadow), var(--tw-ring-shadow), var(--tw-shadow);
   }
-  .outline {
-    outline-style: var(--tw-outline-style);
-    outline-width: 1px;
-  }
   .transition {
     transition-property: color, background-color, border-color, outline-color, text-decoration-color, fill, stroke, --tw-gradient-from, --tw-gradient-via, --tw-gradient-to, opacity, box-shadow, transform, translate, scale, rotate, filter, -webkit-backdrop-filter, backdrop-filter, display, content-visibility, overlay, pointer-events;
     transition-timing-function: var(--tw-ease, var(--default-transition-timing-function));
@@ -1165,11 +1122,6 @@
   inherits: false;
   initial-value: 0 0 #0000;
 }
-@property --tw-outline-style {
-  syntax: "*";
-  inherits: false;
-  initial-value: solid;
-}
 @property --tw-duration {
   syntax: "*";
   inherits: false;
@@ -1205,7 +1157,6 @@
       --tw-ring-offset-width: 0px;
       --tw-ring-offset-color: #fff;
       --tw-ring-offset-shadow: 0 0 #0000;
-      --tw-outline-style: solid;
       --tw-duration: initial;
     }
   }