diff --git a/internal/pkg/alerting/alerter.go b/internal/pkg/alerting/alerter.go
new file mode 100644
index 00000000..5213d382
--- /dev/null
+++ b/internal/pkg/alerting/alerter.go
@@ -0,0 +1,51 @@
+package alerting
+
+import (
+	"context"
+	"time"
+
+	"github.com/stakater/Reloader/internal/pkg/config"
+)
+
+// AlertMessage contains the details of a reload event to be sent as an alert.
+type AlertMessage struct {
+	WorkloadKind      string
+	WorkloadName      string
+	WorkloadNamespace string
+	ResourceKind      string
+	ResourceName      string
+	ResourceNamespace string
+	Timestamp         time.Time
+}
+
+// Alerter is the interface for sending reload notifications.
+type Alerter interface {
+	Send(ctx context.Context, message AlertMessage) error
+}
+
+// NewAlerter creates an Alerter based on the configuration.
+// Returns a NoOpAlerter if alerting is disabled.
+func NewAlerter(cfg *config.Config) Alerter {
+	alertCfg := cfg.Alerting
+	if !alertCfg.Enabled || alertCfg.WebhookURL == "" {
+		return &NoOpAlerter{}
+	}
+
+	switch alertCfg.Sink {
+	case "slack":
+		return NewSlackAlerter(alertCfg.WebhookURL, alertCfg.Proxy, alertCfg.Additional)
+	case "teams":
+		return NewTeamsAlerter(alertCfg.WebhookURL, alertCfg.Proxy, alertCfg.Additional)
+	case "gchat":
+		return NewGChatAlerter(alertCfg.WebhookURL, alertCfg.Proxy, alertCfg.Additional)
+	default:
+		return NewRawAlerter(alertCfg.WebhookURL, alertCfg.Proxy, alertCfg.Additional)
+	}
+}
+
+// NoOpAlerter is an Alerter that does nothing.
+type NoOpAlerter struct{}
+
+func (a *NoOpAlerter) Send(ctx context.Context, message AlertMessage) error {
+	return nil
+}
diff --git a/internal/pkg/alerting/alerter_test.go b/internal/pkg/alerting/alerter_test.go
new file mode 100644
index 00000000..6e5724f4
--- /dev/null
+++ b/internal/pkg/alerting/alerter_test.go
@@ -0,0 +1,267 @@
+package alerting
+
+import (
+	"context"
+	"encoding/json"
+	"net/http"
+	"net/http/httptest"
+	"testing"
+	"time"
+
+	"github.com/stakater/Reloader/internal/pkg/config"
+)
+
+func TestNewAlerter_Disabled(t *testing.T) {
+	cfg := config.NewDefault()
+	cfg.Alerting.Enabled = false
+
+	alerter := NewAlerter(cfg)
+	if _, ok := alerter.(*NoOpAlerter); !ok {
+		t.Error("Expected NoOpAlerter when alerting is disabled")
+	}
+}
+
+func TestNewAlerter_NoWebhookURL(t *testing.T) {
+	cfg := config.NewDefault()
+	cfg.Alerting.Enabled = true
+	cfg.Alerting.WebhookURL = ""
+
+	alerter := NewAlerter(cfg)
+	if _, ok := alerter.(*NoOpAlerter); !ok {
+		t.Error("Expected NoOpAlerter when webhook URL is empty")
+	}
+}
+
+func TestNewAlerter_Slack(t *testing.T) {
+	cfg := config.NewDefault()
+	cfg.Alerting.Enabled = true
+	cfg.Alerting.WebhookURL = "http://example.com/webhook"
+	cfg.Alerting.Sink = "slack"
+
+	alerter := NewAlerter(cfg)
+	if _, ok := alerter.(*SlackAlerter); !ok {
+		t.Error("Expected SlackAlerter for sink=slack")
+	}
+}
+
+func TestNewAlerter_Teams(t *testing.T) {
+	cfg := config.NewDefault()
+	cfg.Alerting.Enabled = true
+	cfg.Alerting.WebhookURL = "http://example.com/webhook"
+	cfg.Alerting.Sink = "teams"
+
+	alerter := NewAlerter(cfg)
+	if _, ok := alerter.(*TeamsAlerter); !ok {
+		t.Error("Expected TeamsAlerter for sink=teams")
+	}
+}
+
+func TestNewAlerter_GChat(t *testing.T) {
+	cfg := config.NewDefault()
+	cfg.Alerting.Enabled = true
+	cfg.Alerting.WebhookURL = "http://example.com/webhook"
+	cfg.Alerting.Sink = "gchat"
+
+	alerter := NewAlerter(cfg)
+	if _, ok := alerter.(*GChatAlerter); !ok {
+		t.Error("Expected GChatAlerter for sink=gchat")
+	}
+}
+
+func TestNewAlerter_Raw(t *testing.T) {
+	cfg := config.NewDefault()
+	cfg.Alerting.Enabled = true
+	cfg.Alerting.WebhookURL = "http://example.com/webhook"
+	cfg.Alerting.Sink = "raw"
+
+	alerter := NewAlerter(cfg)
+	if _, ok := alerter.(*RawAlerter); !ok {
+		t.Error("Expected RawAlerter for sink=raw")
+	}
+}
+
+func TestNewAlerter_DefaultIsRaw(t *testing.T) {
+	cfg := config.NewDefault()
+	cfg.Alerting.Enabled = true
+	cfg.Alerting.WebhookURL = "http://example.com/webhook"
+	cfg.Alerting.Sink = "" // Empty sink should default to raw
+
+	alerter := NewAlerter(cfg)
+	if _, ok := alerter.(*RawAlerter); !ok {
+		t.Error("Expected RawAlerter for empty sink")
+	}
+}
+
+func TestNoOpAlerter_Send(t *testing.T) {
+	alerter := &NoOpAlerter{}
+	err := alerter.Send(context.Background(), AlertMessage{})
+	if err != nil {
+		t.Errorf("NoOpAlerter.Send() error = %v, want nil", err)
+	}
+}
+
+func TestSlackAlerter_Send(t *testing.T) {
+	var receivedBody []byte
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		if r.Method != http.MethodPost {
+			t.Errorf("Expected POST request, got %s", r.Method)
+		}
+		if r.Header.Get("Content-Type") != "application/json" {
+			t.Errorf("Expected Content-Type application/json, got %s", r.Header.Get("Content-Type"))
+		}
+		receivedBody = make([]byte, r.ContentLength)
+		r.Body.Read(receivedBody)
+		w.WriteHeader(http.StatusOK)
+	}))
+	defer server.Close()
+
+	alerter := NewSlackAlerter(server.URL, "", "Test Cluster")
+	msg := AlertMessage{
+		WorkloadKind:      "Deployment",
+		WorkloadName:      "nginx",
+		WorkloadNamespace: "default",
+		ResourceKind:      "ConfigMap",
+		ResourceName:      "nginx-config",
+		ResourceNamespace: "default",
+		Timestamp:         time.Now(),
+	}
+
+	err := alerter.Send(context.Background(), msg)
+	if err != nil {
+		t.Fatalf("SlackAlerter.Send() error = %v", err)
+	}
+
+	var slackMsg slackMessage
+	if err := json.Unmarshal(receivedBody, &slackMsg); err != nil {
+		t.Fatalf("Failed to unmarshal slack message: %v", err)
+	}
+
+	if slackMsg.Text == "" {
+		t.Error("Expected non-empty text in slack message")
+	}
+}
+
+func TestTeamsAlerter_Send(t *testing.T) {
+	var receivedBody []byte
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		receivedBody = make([]byte, r.ContentLength)
+		r.Body.Read(receivedBody)
+		w.WriteHeader(http.StatusOK)
+	}))
+	defer server.Close()
+
+	alerter := NewTeamsAlerter(server.URL, "", "")
+	msg := AlertMessage{
+		WorkloadKind:      "Deployment",
+		WorkloadName:      "nginx",
+		WorkloadNamespace: "default",
+		ResourceKind:      "ConfigMap",
+		ResourceName:      "nginx-config",
+		ResourceNamespace: "default",
+		Timestamp:         time.Now(),
+	}
+
+	err := alerter.Send(context.Background(), msg)
+	if err != nil {
+		t.Fatalf("TeamsAlerter.Send() error = %v", err)
+	}
+
+	var teamsMsg teamsMessage
+	if err := json.Unmarshal(receivedBody, &teamsMsg); err != nil {
+		t.Fatalf("Failed to unmarshal teams message: %v", err)
+	}
+
+	if teamsMsg.Type != "MessageCard" {
+		t.Errorf("Expected @type=MessageCard, got %s", teamsMsg.Type)
+	}
+}
+
+func TestGChatAlerter_Send(t *testing.T) {
+	var receivedBody []byte
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		receivedBody = make([]byte, r.ContentLength)
+		r.Body.Read(receivedBody)
+		w.WriteHeader(http.StatusOK)
+	}))
+	defer server.Close()
+
+	alerter := NewGChatAlerter(server.URL, "", "")
+	msg := AlertMessage{
+		WorkloadKind:      "Deployment",
+		WorkloadName:      "nginx",
+		WorkloadNamespace: "default",
+		ResourceKind:      "ConfigMap",
+		ResourceName:      "nginx-config",
+		ResourceNamespace: "default",
+		Timestamp:         time.Now(),
+	}
+
+	err := alerter.Send(context.Background(), msg)
+	if err != nil {
+		t.Fatalf("GChatAlerter.Send() error = %v", err)
+	}
+
+	var gchatMsg gchatMessage
+	if err := json.Unmarshal(receivedBody, &gchatMsg); err != nil {
+		t.Fatalf("Failed to unmarshal gchat message: %v", err)
+	}
+
+	if len(gchatMsg.Cards) != 1 {
+		t.Errorf("Expected 1 card, got %d", len(gchatMsg.Cards))
+	}
+}
+
+func TestRawAlerter_Send(t *testing.T) {
+	var receivedBody []byte
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		receivedBody = make([]byte, r.ContentLength)
+		r.Body.Read(receivedBody)
+		w.WriteHeader(http.StatusOK)
+	}))
+	defer server.Close()
+
+	alerter := NewRawAlerter(server.URL, "", "custom-info")
+	msg := AlertMessage{
+		WorkloadKind:      "Deployment",
+		WorkloadName:      "nginx",
+		WorkloadNamespace: "default",
+		ResourceKind:      "ConfigMap",
+		ResourceName:      "nginx-config",
+		ResourceNamespace: "default",
+		Timestamp:         time.Now(),
+	}
+
+	err := alerter.Send(context.Background(), msg)
+	if err != nil {
+		t.Fatalf("RawAlerter.Send() error = %v", err)
+	}
+
+	var rawMsg rawMessage
+	if err := json.Unmarshal(receivedBody, &rawMsg); err != nil {
+		t.Fatalf("Failed to unmarshal raw message: %v", err)
+	}
+
+	if rawMsg.Event != "reload" {
+		t.Errorf("Expected event=reload, got %s", rawMsg.Event)
+	}
+	if rawMsg.WorkloadName != "nginx" {
+		t.Errorf("Expected workloadName=nginx, got %s", rawMsg.WorkloadName)
+	}
+	if rawMsg.Additional != "custom-info" {
+		t.Errorf("Expected additional=custom-info, got %s", rawMsg.Additional)
+	}
+}
+
+func TestAlerter_WebhookError(t *testing.T) {
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.WriteHeader(http.StatusInternalServerError)
+		w.Write([]byte("Internal Server Error"))
+	}))
+	defer server.Close()
+
+	alerter := NewRawAlerter(server.URL, "", "")
+	err := alerter.Send(context.Background(), AlertMessage{})
+	if err == nil {
+		t.Error("Expected error for non-2xx response")
+	}
+}
diff --git a/internal/pkg/alerting/gchat.go b/internal/pkg/alerting/gchat.go
new file mode 100644
index 00000000..73e2b303
--- /dev/null
+++ b/internal/pkg/alerting/gchat.go
@@ -0,0 +1,90 @@
+package alerting
+
+import (
+	"context"
+	"encoding/json"
+	"fmt"
+)
+
+// GChatAlerter sends alerts to Google Chat webhooks.
+type GChatAlerter struct {
+	webhookURL string
+	additional string
+	client     *httpClient
+}
+
+// NewGChatAlerter creates a new GChatAlerter.
+func NewGChatAlerter(webhookURL, proxyURL, additional string) *GChatAlerter {
+	return &GChatAlerter{
+		webhookURL: webhookURL,
+		additional: additional,
+		client:     newHTTPClient(proxyURL),
+	}
+}
+
+// gchatMessage represents a Google Chat message.
+type gchatMessage struct {
+	Text  string       `json:"text,omitempty"`
+	Cards []gchatCard  `json:"cards,omitempty"`
+}
+
+type gchatCard struct {
+	Header   gchatHeader    `json:"header"`
+	Sections []gchatSection `json:"sections"`
+}
+
+type gchatHeader struct {
+	Title    string `json:"title"`
+	Subtitle string `json:"subtitle,omitempty"`
+}
+
+type gchatSection struct {
+	Widgets []gchatWidget `json:"widgets"`
+}
+
+type gchatWidget struct {
+	KeyValue *gchatKeyValue `json:"keyValue,omitempty"`
+}
+
+type gchatKeyValue struct {
+	TopLabel string `json:"topLabel"`
+	Content  string `json:"content"`
+}
+
+func (a *GChatAlerter) Send(ctx context.Context, message AlertMessage) error {
+	msg := a.buildMessage(message)
+
+	body, err := json.Marshal(msg)
+	if err != nil {
+		return fmt.Errorf("marshaling gchat message: %w", err)
+	}
+
+	return a.client.post(ctx, a.webhookURL, body)
+}
+
+func (a *GChatAlerter) buildMessage(msg AlertMessage) gchatMessage {
+	widgets := []gchatWidget{
+		{KeyValue: &gchatKeyValue{TopLabel: "Workload", Content: fmt.Sprintf("%s/%s (%s)", msg.WorkloadNamespace, msg.WorkloadName, msg.WorkloadKind)}},
+		{KeyValue: &gchatKeyValue{TopLabel: "Resource", Content: fmt.Sprintf("%s/%s (%s)", msg.ResourceNamespace, msg.ResourceName, msg.ResourceKind)}},
+		{KeyValue: &gchatKeyValue{TopLabel: "Time", Content: msg.Timestamp.Format("2006-01-02 15:04:05 UTC")}},
+	}
+
+	subtitle := ""
+	if a.additional != "" {
+		subtitle = a.additional
+	}
+
+	return gchatMessage{
+		Cards: []gchatCard{
+			{
+				Header: gchatHeader{
+					Title:    "Reloader triggered reload",
+					Subtitle: subtitle,
+				},
+				Sections: []gchatSection{
+					{Widgets: widgets},
+				},
+			},
+		},
+	}
+}
diff --git a/internal/pkg/alerting/http.go b/internal/pkg/alerting/http.go
new file mode 100644
index 00000000..827091e7
--- /dev/null
+++ b/internal/pkg/alerting/http.go
@@ -0,0 +1,57 @@
+package alerting
+
+import (
+	"bytes"
+	"context"
+	"fmt"
+	"io"
+	"net/http"
+	"net/url"
+	"time"
+)
+
+// httpClient wraps http.Client with common configuration.
+type httpClient struct {
+	client *http.Client
+}
+
+// newHTTPClient creates a new httpClient with optional proxy support.
+func newHTTPClient(proxyURL string) *httpClient {
+	transport := &http.Transport{}
+
+	if proxyURL != "" {
+		proxy, err := url.Parse(proxyURL)
+		if err == nil {
+			transport.Proxy = http.ProxyURL(proxy)
+		}
+	}
+
+	return &httpClient{
+		client: &http.Client{
+			Transport: transport,
+			Timeout:   10 * time.Second,
+		},
+	}
+}
+
+// post sends a POST request with JSON body.
+func (c *httpClient) post(ctx context.Context, url string, body []byte) error {
+	req, err := http.NewRequestWithContext(ctx, http.MethodPost, url, bytes.NewReader(body))
+	if err != nil {
+		return fmt.Errorf("creating request: %w", err)
+	}
+	req.Header.Set("Content-Type", "application/json")
+
+	resp, err := c.client.Do(req)
+	if err != nil {
+		return fmt.Errorf("sending request: %w", err)
+	}
+	defer resp.Body.Close()
+
+	if resp.StatusCode < 200 || resp.StatusCode >= 300 {
+		body, _ := io.ReadAll(resp.Body)
+		return fmt.Errorf("unexpected status %d: %s", resp.StatusCode, string(body))
+	}
+
+	return nil
+}
diff --git a/internal/pkg/alerting/raw.go b/internal/pkg/alerting/raw.go
new file mode 100644
index 00000000..ad0add08
--- /dev/null
+++ b/internal/pkg/alerting/raw.go
@@ -0,0 +1,57 @@
+package alerting
+
+import (
+	"context"
+	"encoding/json"
+	"fmt"
+)
+
+// RawAlerter sends alerts as raw JSON to a webhook.
+type RawAlerter struct {
+	webhookURL string
+	additional string
+	client     *httpClient
+}
+
+// NewRawAlerter creates a new RawAlerter.
+func NewRawAlerter(webhookURL, proxyURL, additional string) *RawAlerter {
+	return &RawAlerter{
+		webhookURL: webhookURL,
+		additional: additional,
+		client:     newHTTPClient(proxyURL),
+	}
+}
+
+// rawMessage is the JSON payload for raw webhook alerts.
+type rawMessage struct {
+	Event             string `json:"event"`
+	WorkloadKind      string `json:"workloadKind"`
+	WorkloadName      string `json:"workloadName"`
+	WorkloadNamespace string `json:"workloadNamespace"`
+	ResourceKind      string `json:"resourceKind"`
+	ResourceName      string `json:"resourceName"`
+	ResourceNamespace string `json:"resourceNamespace"`
+	Timestamp         string `json:"timestamp"`
+	Additional        string `json:"additional,omitempty"`
+}
+
+func (a *RawAlerter) Send(ctx context.Context, message AlertMessage) error {
+	msg := rawMessage{
+		Event:             "reload",
+		WorkloadKind:      message.WorkloadKind,
+		WorkloadName:      message.WorkloadName,
+		WorkloadNamespace: message.WorkloadNamespace,
+		ResourceKind:      message.ResourceKind,
+		ResourceName:      message.ResourceName,
+		ResourceNamespace: message.ResourceNamespace,
+		Timestamp:         message.Timestamp.Format("2006-01-02T15:04:05Z07:00"),
+		Additional:        a.additional,
+	}
+
+	body, err := json.Marshal(msg)
+	if err != nil {
+		return fmt.Errorf("marshaling raw message: %w", err)
+	}
+
+	return a.client.post(ctx, a.webhookURL, body)
+}
diff --git a/internal/pkg/alerting/slack.go b/internal/pkg/alerting/slack.go
new file mode 100644
index 00000000..1b917118
--- /dev/null
+++ b/internal/pkg/alerting/slack.go
@@ -0,0 +1,57 @@
+package alerting
+
+import (
+	"context"
+	"encoding/json"
+	"fmt"
+)
+
+// SlackAlerter sends alerts to Slack webhooks.
+type SlackAlerter struct {
+	webhookURL string
+	additional string
+	client     *httpClient
+}
+
+// NewSlackAlerter creates a new SlackAlerter.
+func NewSlackAlerter(webhookURL, proxyURL, additional string) *SlackAlerter {
+	return &SlackAlerter{
+		webhookURL: webhookURL,
+		additional: additional,
+		client:     newHTTPClient(proxyURL),
+	}
+}
+
+type slackMessage struct {
+	Text string `json:"text"`
+}
+
+func (a *SlackAlerter) Send(ctx context.Context, message AlertMessage) error {
+	text := a.formatMessage(message)
+	msg := slackMessage{Text: text}
+
+	body, err := json.Marshal(msg)
+	if err != nil {
+		return fmt.Errorf("marshaling slack message: %w", err)
+	}
+
+	return a.client.post(ctx, a.webhookURL, body)
+}
+
+func (a *SlackAlerter) formatMessage(msg AlertMessage) string {
+	text := fmt.Sprintf(
+		"Reloader triggered reload\n"+
+			"*Workload:* %s/%s (%s)\n"+
+			"*Resource:* %s/%s (%s)\n"+
+			"*Time:* %s",
+		msg.WorkloadNamespace, msg.WorkloadName, msg.WorkloadKind,
+		msg.ResourceNamespace, msg.ResourceName, msg.ResourceKind,
+		msg.Timestamp.Format("2006-01-02 15:04:05 UTC"),
+	)
+
+	if a.additional != "" {
+		text = a.additional + "\n" + text
+	}
+
+	return text
+}
diff --git a/internal/pkg/alerting/teams.go b/internal/pkg/alerting/teams.go
new file mode 100644
index 00000000..99b08d5c
--- /dev/null
+++ b/internal/pkg/alerting/teams.go
@@ -0,0 +1,81 @@
+package alerting
+
+import (
+	"context"
+	"encoding/json"
+	"fmt"
+)
+
+// TeamsAlerter sends alerts to Microsoft Teams webhooks.
+type TeamsAlerter struct {
+	webhookURL string
+	additional string
+	client     *httpClient
+}
+
+// NewTeamsAlerter creates a new TeamsAlerter.
+func NewTeamsAlerter(webhookURL, proxyURL, additional string) *TeamsAlerter {
+	return &TeamsAlerter{
+		webhookURL: webhookURL,
+		additional: additional,
+		client:     newHTTPClient(proxyURL),
+	}
+}
+
+// teamsMessage represents a Microsoft Teams message card.
+type teamsMessage struct {
+	Type       string         `json:"@type"`
+	Context    string         `json:"@context"`
+	ThemeColor string         `json:"themeColor"`
+	Summary    string         `json:"summary"`
+	Sections   []teamsSection `json:"sections"`
+}
+
+type teamsSection struct {
+	ActivityTitle    string      `json:"activityTitle"`
+	ActivitySubtitle string      `json:"activitySubtitle,omitempty"`
+	Facts            []teamsFact `json:"facts"`
+}
+
+type teamsFact struct {
+	Name  string `json:"name"`
+	Value string `json:"value"`
+}
+
+func (a *TeamsAlerter) Send(ctx context.Context, message AlertMessage) error {
+	msg := a.buildMessage(message)
+
+	body, err := json.Marshal(msg)
+	if err != nil {
+		return fmt.Errorf("marshaling teams message: %w", err)
+	}
+
+	return a.client.post(ctx, a.webhookURL, body)
+}
+
+func (a *TeamsAlerter) buildMessage(msg AlertMessage) teamsMessage {
+	facts := []teamsFact{
+		{Name: "Workload", Value: fmt.Sprintf("%s/%s (%s)", msg.WorkloadNamespace, msg.WorkloadName, msg.WorkloadKind)},
+		{Name: "Resource", Value: fmt.Sprintf("%s/%s (%s)", msg.ResourceNamespace, msg.ResourceName, msg.ResourceKind)},
+		{Name: "Time", Value: msg.Timestamp.Format("2006-01-02 15:04:05 UTC")},
+	}
+
+	subtitle := ""
+	if a.additional != "" {
+		subtitle = a.additional
+	}
+
+	return teamsMessage{
+		Type:       "MessageCard",
+		Context:    "http://schema.org/extensions",
+		ThemeColor: "0076D7",
+		Summary:    "Reloader triggered reload",
+		Sections: []teamsSection{
+			{
+				ActivityTitle:    "Reloader triggered reload",
+				ActivitySubtitle: subtitle,
+				Facts:            facts,
+			},
+		},
+	}
+}
diff --git a/internal/pkg/config/config.go b/internal/pkg/config/config.go
index 6288d5f9..9ce3e0ce 100644
--- a/internal/pkg/config/config.go
+++ b/internal/pkg/config/config.go
@@ -140,9 +140,20 @@ type AnnotationConfig struct {
 
 // AlertingConfig holds configuration for alerting integrations.
 type AlertingConfig struct {
-	SlackWebhookURL string
-	TeamsWebhookURL string
-	GChatWebhookURL string
+	// Enabled enables alerting notifications on reload events.
+	Enabled bool
+
+	// WebhookURL is the webhook URL to send alerts to.
+	WebhookURL string
+
+	// Sink determines the alert format: "slack", "teams", "gchat", or "raw" (default).
+	Sink string
+
+	// Proxy is an optional HTTP proxy for webhook requests.
+	Proxy string
+
+	// Additional is optional context prepended to alert messages.
+	Additional string
 }
 
 // LeaderElectionConfig holds configuration for leader election.
diff --git a/internal/pkg/controller/deployment_reconciler.go b/internal/pkg/controller/deployment_reconciler.go
new file mode 100644
index 00000000..d28272c5
--- /dev/null
+++ b/internal/pkg/controller/deployment_reconciler.go
@@ -0,0 +1,89 @@
+package controller
+
+import (
+	"context"
+
+	"github.com/go-logr/logr"
+	"github.com/stakater/Reloader/internal/pkg/config"
+	"github.com/stakater/Reloader/internal/pkg/reload"
+	appsv1 "k8s.io/api/apps/v1"
+	"k8s.io/apimachinery/pkg/api/errors"
+	ctrl "sigs.k8s.io/controller-runtime"
+	"sigs.k8s.io/controller-runtime/pkg/client"
+	"sigs.k8s.io/controller-runtime/pkg/predicate"
+)
+
+// DeploymentReconciler reconciles Deployment objects to handle pause expiration.
+// This reconciler watches for deployments that were paused by Reloader and
+// unpauses them when the pause period expires.
+type DeploymentReconciler struct {
+	client.Client
+	Log          logr.Logger
+	Config       *config.Config
+	PauseHandler *reload.PauseHandler
+}
+
+// Reconcile handles Deployment pause expiration.
+func (r *DeploymentReconciler) Reconcile(ctx context.Context, req ctrl.Request) (ctrl.Result, error) {
+	log := r.Log.WithValues("deployment", req.NamespacedName)
+
+	var deploy appsv1.Deployment
+	if err := r.Get(ctx, req.NamespacedName, &deploy); err != nil {
+		if errors.IsNotFound(err) {
+			return ctrl.Result{}, nil
+		}
+		return ctrl.Result{}, err
+	}
+
+	// Check if this deployment was paused by Reloader
+	if !r.PauseHandler.IsPausedByReloader(&deploy) {
+		return ctrl.Result{}, nil
+	}
+
+	// Check if pause period has expired
+	expired, remainingTime, err := r.PauseHandler.CheckPauseExpired(&deploy)
+	if err != nil {
+		log.Error(err, "Failed to check pause expiration")
+		return ctrl.Result{}, err
+	}
+
+	if !expired {
+		// Still within pause period - requeue to check again
+		log.V(1).Info("Deployment pause not yet expired", "remaining", remainingTime)
+		return ctrl.Result{RequeueAfter: remainingTime}, nil
+	}
+
+	// Pause period has expired - unpause the deployment
+	log.Info("Unpausing deployment after pause period expired")
+	r.PauseHandler.ClearPause(&deploy)
+
+	if err := r.Update(ctx, &deploy, client.FieldOwner(FieldManager)); err != nil {
+		log.Error(err, "Failed to unpause deployment")
+		return ctrl.Result{}, err
+	}
+
+	return ctrl.Result{}, nil
+}
+
+// SetupWithManager sets up the DeploymentReconciler with the manager.
+func (r *DeploymentReconciler) SetupWithManager(mgr ctrl.Manager) error {
+	return ctrl.NewControllerManagedBy(mgr).
+		For(&appsv1.Deployment{}).
+		WithEventFilter(r.pausedByReloaderPredicate()).
+		Complete(r)
+}
+
+// pausedByReloaderPredicate returns a predicate that only selects deployments
+// that have been paused by Reloader (have the paused-at annotation).
+func (r *DeploymentReconciler) pausedByReloaderPredicate() predicate.Predicate {
+	return predicate.NewPredicateFuncs(func(obj client.Object) bool {
+		annotations := obj.GetAnnotations()
+		if annotations == nil {
+			return false
+		}
+
+		// Only process if deployment has our paused-at annotation
+		_, hasPausedAt := annotations[r.Config.Annotations.PausedAt]
+		return hasPausedAt
+	})
+}
diff --git a/internal/pkg/controller/retry.go b/internal/pkg/controller/retry.go
index f81e8e92..f8af3de0 100644
--- a/internal/pkg/controller/retry.go
+++ b/internal/pkg/controller/retry.go
@@ -2,16 +2,23 @@ package controller
 
 import (
 	"context"
+	"maps"
 
 	"github.com/stakater/Reloader/internal/pkg/reload"
 	"github.com/stakater/Reloader/internal/pkg/workload"
+	batchv1 "k8s.io/api/batch/v1"
 	"k8s.io/apimachinery/pkg/api/errors"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 	"k8s.io/client-go/util/retry"
 	"sigs.k8s.io/controller-runtime/pkg/client"
 )
 
 // UpdateWorkloadWithRetry updates a workload with exponential backoff on conflict.
 // On conflict, it re-fetches the object, re-applies the reload changes, and retries.
+// For Jobs and CronJobs, special handling is applied:
+// - Jobs are deleted and recreated with the same spec
+// - CronJobs create a new Job from their template
+// For Argo Rollouts, special handling is applied based on the rollout strategy annotation.
 func UpdateWorkloadWithRetry(
 	ctx context.Context,
 	c client.Client,
@@ -22,6 +29,31 @@ func UpdateWorkloadWithRetry(
 	namespace string,
 	hash string,
 	autoReload bool,
+) (bool, error) {
+	// Handle special workload types
+	switch wl.Kind() {
+	case workload.KindJob:
+		return updateJobWithRecreate(ctx, c, reloadService, wl, resourceName, resourceType, namespace, hash, autoReload)
+	case workload.KindCronJob:
+		return updateCronJobWithNewJob(ctx, c, reloadService, wl, resourceName, resourceType, namespace, hash, autoReload)
+	case workload.KindArgoRollout:
+		return updateArgoRollout(ctx, c, reloadService, wl, resourceName, resourceType, namespace, hash, autoReload)
+	default:
+		return updateStandardWorkload(ctx, c, reloadService, wl, resourceName, resourceType, namespace, hash, autoReload)
+	}
+}
+
+// updateStandardWorkload updates Deployments, DaemonSets, StatefulSets, etc.
+func updateStandardWorkload(
+	ctx context.Context,
+	c client.Client,
+	reloadService *reload.Service,
+	wl workload.WorkloadAccessor,
+	resourceName string,
+	resourceType reload.ResourceType,
+	namespace string,
+	hash string,
+	autoReload bool,
 ) (bool, error) {
 	var updated bool
 	isFirstAttempt := true
@@ -66,3 +98,202 @@ func UpdateWorkloadWithRetry(
 
 	return updated, err
 }
+
+// updateJobWithRecreate deletes the Job and recreates it with the updated spec.
+// Jobs are immutable after creation, so we must delete and recreate.
+func updateJobWithRecreate(
+	ctx context.Context,
+	c client.Client,
+	reloadService *reload.Service,
+	wl workload.WorkloadAccessor,
+	resourceName string,
+	resourceType reload.ResourceType,
+	namespace string,
+	hash string,
+	autoReload bool,
+) (bool, error) {
+	jobWl, ok := wl.(*workload.JobWorkload)
+	if !ok {
+		return false, nil
+	}
+
+	// Apply reload changes to the workload
+	updated, err := reloadService.ApplyReload(
+		ctx,
+		wl,
+		resourceName,
+		resourceType,
+		namespace,
+		hash,
+		autoReload,
+	)
+	if err != nil {
+		return false, err
+	}
+
+	if !updated {
+		return false, nil
+	}
+
+	oldJob := jobWl.GetJob()
+	newJob := oldJob.DeepCopy()
+
+	// Delete the old job with background propagation
+	policy := metav1.DeletePropagationBackground
+	if err := c.Delete(ctx, oldJob, &client.DeleteOptions{
+		PropagationPolicy: &policy,
+	}); err != nil {
+		if !errors.IsNotFound(err) {
+			return false, err
+		}
+	}
+
+	// Clear fields that should not be specified when creating a new Job
+	newJob.ResourceVersion = ""
+	newJob.UID = ""
+	newJob.CreationTimestamp = metav1.Time{}
+	newJob.Status = batchv1.JobStatus{}
+
+	// Remove problematic labels that are auto-generated
+	delete(newJob.Spec.Template.Labels, "controller-uid")
+	delete(newJob.Spec.Template.Labels, batchv1.ControllerUidLabel)
+	delete(newJob.Spec.Template.Labels, batchv1.JobNameLabel)
+	delete(newJob.Spec.Template.Labels, "job-name")
+
+	// Remove the selector to allow it to be auto-generated
+	newJob.Spec.Selector = nil
+
+	// Create the new job with same spec
+	if err := c.Create(ctx, newJob, client.FieldOwner(FieldManager)); err != nil {
+		return false, err
+	}
+
+	return true, nil
+}
+
+// updateCronJobWithNewJob creates a new Job from the CronJob's template.
+// CronJobs don't get updated directly; instead, a new Job is triggered.
+func updateCronJobWithNewJob(
+	ctx context.Context,
+	c client.Client,
+	reloadService *reload.Service,
+	wl workload.WorkloadAccessor,
+	resourceName string,
+	resourceType reload.ResourceType,
+	namespace string,
+	hash string,
+	autoReload bool,
+) (bool, error) {
+	cronJobWl, ok := wl.(*workload.CronJobWorkload)
+	if !ok {
+		return false, nil
+	}
+
+	// Apply reload changes to get the updated spec
+	updated, err := reloadService.ApplyReload(
+		ctx,
+		wl,
+		resourceName,
+		resourceType,
+		namespace,
+		hash,
+		autoReload,
+	)
+	if err != nil {
+		return false, err
+	}
+
+	if !updated {
+		return false, nil
+	}
+
+	cronJob := cronJobWl.GetCronJob()
+
+	// Build annotations for the new Job
+	annotations := make(map[string]string)
+	annotations["cronjob.kubernetes.io/instantiate"] = "manual"
+	maps.Copy(annotations, cronJob.Spec.JobTemplate.Annotations)
+
+	// Create a new Job from the CronJob template
+	job := &batchv1.Job{
+		ObjectMeta: metav1.ObjectMeta{
+			GenerateName: cronJob.Name + "-",
+			Namespace:    cronJob.Namespace,
+			Annotations:  annotations,
+			Labels:       cronJob.Spec.JobTemplate.Labels,
+			OwnerReferences: []metav1.OwnerReference{
+				*metav1.NewControllerRef(cronJob, batchv1.SchemeGroupVersion.WithKind("CronJob")),
+			},
+		},
+		Spec: cronJob.Spec.JobTemplate.Spec,
+	}
+
+	if err := c.Create(ctx, job, client.FieldOwner(FieldManager)); err != nil {
+		return false, err
+	}
+
+	return true, nil
+}
+
+// updateArgoRollout updates an Argo Rollout using its custom Update method.
+// This handles the rollout strategy annotation to determine whether to do
+// a standard rollout or set the restartAt field.
+func updateArgoRollout(
+	ctx context.Context,
+	c client.Client,
+	reloadService *reload.Service,
+	wl workload.WorkloadAccessor,
+	resourceName string,
+	resourceType reload.ResourceType,
+	namespace string,
+	hash string,
+	autoReload bool,
+) (bool, error) {
+	rolloutWl, ok := wl.(*workload.RolloutWorkload)
+	if !ok {
+		return false, nil
+	}
+
+	var updated bool
+	isFirstAttempt := true
+
+	err := retry.RetryOnConflict(retry.DefaultBackoff, func() error {
+		// On retry, re-fetch the object to get the latest ResourceVersion
+		if !isFirstAttempt {
+			obj := rolloutWl.GetObject()
+			key := client.ObjectKeyFromObject(obj)
+			if err := c.Get(ctx, key, obj); err != nil {
+				if errors.IsNotFound(err) {
+					// Object was deleted, nothing to update
+					return nil
+				}
+				return err
+			}
+		}
+		isFirstAttempt = false
+
+		// Apply reload changes (this modifies the workload in-place)
+		var applyErr error
+		updated, applyErr = reloadService.ApplyReload(
+			ctx,
+			wl,
+			resourceName,
+			resourceType,
+			namespace,
+			hash,
+			autoReload,
+		)
+		if applyErr != nil {
+			return applyErr
+		}
+
+		if !updated {
+			return nil
+		}
+
+		// Use the RolloutWorkload's Update method which handles the rollout strategy
+		return rolloutWl.Update(ctx, c)
+	})
+
+	return updated, err
+}
diff --git a/internal/pkg/reload/pause.go b/internal/pkg/reload/pause.go
new file mode 100644
index 00000000..1d00d313
--- /dev/null
+++ b/internal/pkg/reload/pause.go
@@ -0,0 +1,130 @@
+package reload
+
+import (
+	"fmt"
+	"time"
+
+	"github.com/stakater/Reloader/internal/pkg/config"
+	"github.com/stakater/Reloader/internal/pkg/workload"
+	appsv1 "k8s.io/api/apps/v1"
+)
+
+// PauseHandler handles pause deployment logic.
+type PauseHandler struct {
+	cfg *config.Config
+}
+
+// NewPauseHandler creates a new PauseHandler.
+func NewPauseHandler(cfg *config.Config) *PauseHandler {
+	return &PauseHandler{cfg: cfg}
+}
+
+// ShouldPause checks if a deployment should be paused after reload.
+func (h *PauseHandler) ShouldPause(wl workload.WorkloadAccessor) bool {
+	if wl.Kind() != workload.KindDeployment {
+		return false
+	}
+
+	annotations := wl.GetAnnotations()
+	if annotations == nil {
+		return false
+	}
+
+	pausePeriod := annotations[h.cfg.Annotations.PausePeriod]
+	return pausePeriod != ""
+}
+
+// GetPausePeriod returns the configured pause period for a workload.
+func (h *PauseHandler) GetPausePeriod(wl workload.WorkloadAccessor) (time.Duration, error) {
+	annotations := wl.GetAnnotations()
+	if annotations == nil {
+		return 0, fmt.Errorf("no annotations on workload")
+	}
+
+	pausePeriodStr := annotations[h.cfg.Annotations.PausePeriod]
+	if pausePeriodStr == "" {
+		return 0, fmt.Errorf("no pause period annotation")
+	}
+
+	return time.ParseDuration(pausePeriodStr)
+}
+
+// ApplyPause pauses a deployment and sets the paused-at annotation.
+func (h *PauseHandler) ApplyPause(wl workload.WorkloadAccessor) error {
+	deployWl, ok := wl.(*workload.DeploymentWorkload)
+	if !ok {
+		return fmt.Errorf("workload is not a deployment")
+	}
+
+	deploy := deployWl.GetDeployment()
+
+	// Set paused flag
+	deploy.Spec.Paused = true
+
+	// Set paused-at annotation
+	if deploy.Annotations == nil {
+		deploy.Annotations = make(map[string]string)
+	}
+	deploy.Annotations[h.cfg.Annotations.PausedAt] = time.Now().UTC().Format(time.RFC3339)
+
+	return nil
+}
+
+// CheckPauseExpired checks if the pause period has expired for a deployment.
+func (h *PauseHandler) CheckPauseExpired(deploy *appsv1.Deployment) (expired bool, remainingTime time.Duration, err error) {
+	annotations := deploy.GetAnnotations()
+	if annotations == nil {
+		return false, 0, fmt.Errorf("no annotations on deployment")
+	}
+
+	pausePeriodStr := annotations[h.cfg.Annotations.PausePeriod]
+	if pausePeriodStr == "" {
+		return false, 0, fmt.Errorf("no pause period annotation")
+	}
+
+	pausedAtStr := annotations[h.cfg.Annotations.PausedAt]
+	if pausedAtStr == "" {
+		return false, 0, fmt.Errorf("no paused-at annotation")
+	}
+
+	pausePeriod, err := time.ParseDuration(pausePeriodStr)
+	if err != nil {
+		return false, 0, fmt.Errorf("invalid pause period %q: %w", pausePeriodStr, err)
+	}
+
+	pausedAt, err := time.Parse(time.RFC3339, pausedAtStr)
+	if err != nil {
+		return false, 0, fmt.Errorf("invalid paused-at time %q: %w", pausedAtStr, err)
+	}
+
+	elapsed := time.Since(pausedAt)
+	if elapsed >= pausePeriod {
+		return true, 0, nil
+	}
+
+	return false, pausePeriod - elapsed, nil
+}
+
+// ClearPause removes the pause from a deployment.
+func (h *PauseHandler) ClearPause(deploy *appsv1.Deployment) {
+	deploy.Spec.Paused = false
+	delete(deploy.Annotations, h.cfg.Annotations.PausedAt)
+	// Keep pause-period annotation (user's config)
+}
+
+// IsPausedByReloader checks if a deployment was paused by Reloader.
+func (h *PauseHandler) IsPausedByReloader(deploy *appsv1.Deployment) bool {
+	if !deploy.Spec.Paused {
+		return false
+	}
+
+	annotations := deploy.GetAnnotations()
+	if annotations == nil {
+		return false
+	}
+
+	_, hasPausedAt := annotations[h.cfg.Annotations.PausedAt]
+	_, hasPausePeriod := annotations[h.cfg.Annotations.PausePeriod]
+
+	return hasPausedAt && hasPausePeriod
+}
diff --git a/internal/pkg/reload/pause_test.go b/internal/pkg/reload/pause_test.go
new file mode 100644
index 00000000..9c7992d0
--- /dev/null
+++ b/internal/pkg/reload/pause_test.go
@@ -0,0 +1,327 @@
+package reload
+
+import (
+	"testing"
+	"time"
+
+	"github.com/stakater/Reloader/internal/pkg/config"
+	"github.com/stakater/Reloader/internal/pkg/workload"
+	appsv1 "k8s.io/api/apps/v1"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
+)
+
+func TestPauseHandler_ShouldPause(t *testing.T) {
+	cfg := config.NewDefault()
+	handler := NewPauseHandler(cfg)
+
+	tests := []struct {
+		name     string
+		workload workload.WorkloadAccessor
+		want     bool
+	}{
+		{
+			name: "deployment with pause period",
+			workload: workload.NewDeploymentWorkload(&appsv1.Deployment{
+				ObjectMeta: metav1.ObjectMeta{
+					Annotations: map[string]string{
+						cfg.Annotations.PausePeriod: "5m",
+					},
+				},
+			}),
+			want: true,
+		},
+		{
+			name: "deployment without pause period",
+			workload: workload.NewDeploymentWorkload(&appsv1.Deployment{
+				ObjectMeta: metav1.ObjectMeta{},
+			}),
+			want: false,
+		},
+		{
+			name: "daemonset with pause period (ignored)",
+			workload: workload.NewDaemonSetWorkload(&appsv1.DaemonSet{
+				ObjectMeta: metav1.ObjectMeta{
+					Annotations: map[string]string{
+						cfg.Annotations.PausePeriod: "5m",
+					},
+				},
+			}),
+			want: false,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			got := handler.ShouldPause(tt.workload)
+			if got != tt.want {
+				t.Errorf("ShouldPause() = %v, want %v", got, tt.want)
+			}
+		})
+	}
+}
+
+func TestPauseHandler_GetPausePeriod(t *testing.T) {
+	cfg := config.NewDefault()
+	handler := NewPauseHandler(cfg)
+
+	tests := []struct {
+		name        string
+		workload    workload.WorkloadAccessor
+		wantPeriod  time.Duration
+		wantErr     bool
+	}{
+		{
+			name: "valid pause period",
+			workload: workload.NewDeploymentWorkload(&appsv1.Deployment{
+				ObjectMeta: metav1.ObjectMeta{
+					Annotations: map[string]string{
+						cfg.Annotations.PausePeriod: "5m",
+					},
+				},
+			}),
+			wantPeriod: 5 * time.Minute,
+			wantErr:    false,
+		},
+		{
+			name: "invalid pause period",
+			workload: workload.NewDeploymentWorkload(&appsv1.Deployment{
+				ObjectMeta: metav1.ObjectMeta{
+					Annotations: map[string]string{
+						cfg.Annotations.PausePeriod: "invalid",
+					},
+				},
+			}),
+			wantErr: true,
+		},
+		{
+			name: "no pause period annotation",
+			workload: workload.NewDeploymentWorkload(&appsv1.Deployment{
+				ObjectMeta: metav1.ObjectMeta{},
+			}),
+			wantErr: true,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			got, err := handler.GetPausePeriod(tt.workload)
+			if (err != nil) != tt.wantErr {
+				t.Errorf("GetPausePeriod() error = %v, wantErr %v", err, tt.wantErr)
+				return
+			}
+			if !tt.wantErr && got != tt.wantPeriod {
+				t.Errorf("GetPausePeriod() = %v, want %v", got, tt.wantPeriod)
+			}
+		})
+	}
+}
+
+func TestPauseHandler_ApplyPause(t *testing.T) {
+	cfg := config.NewDefault()
+	handler := NewPauseHandler(cfg)
+
+	deploy := &appsv1.Deployment{
+		ObjectMeta: metav1.ObjectMeta{
+			Name: "test-deploy",
+		},
+		Spec: appsv1.DeploymentSpec{
+			Paused: false,
+		},
+	}
+
+	wl := workload.NewDeploymentWorkload(deploy)
+	err := handler.ApplyPause(wl)
+	if err != nil {
+		t.Fatalf("ApplyPause() error = %v", err)
+	}
+
+	if !deploy.Spec.Paused {
+		t.Error("Expected deployment to be paused")
+	}
+
+	pausedAt := deploy.Annotations[cfg.Annotations.PausedAt]
+	if pausedAt == "" {
+		t.Error("Expected paused-at annotation to be set")
+	}
+
+	// Verify the timestamp is valid
+	_, err = time.Parse(time.RFC3339, pausedAt)
+	if err != nil {
+		t.Errorf("Invalid paused-at timestamp: %v", err)
+	}
+}
+
+func TestPauseHandler_CheckPauseExpired(t *testing.T) {
+	cfg := config.NewDefault()
+	handler := NewPauseHandler(cfg)
+
+	tests := []struct {
+		name        string
+		deploy      *appsv1.Deployment
+		wantExpired bool
+		wantErr     bool
+	}{
+		{
+			name: "pause expired",
+			deploy: &appsv1.Deployment{
+				ObjectMeta: metav1.ObjectMeta{
+					Annotations: map[string]string{
+						cfg.Annotations.PausePeriod: "1ms",
+						cfg.Annotations.PausedAt:    time.Now().Add(-time.Second).UTC().Format(time.RFC3339),
+					},
+				},
+				Spec: appsv1.DeploymentSpec{Paused: true},
+			},
+			wantExpired: true,
+			wantErr:     false,
+		},
+		{
+			name: "pause not expired",
+			deploy: &appsv1.Deployment{
+				ObjectMeta: metav1.ObjectMeta{
+					Annotations: map[string]string{
+						cfg.Annotations.PausePeriod: "1h",
+						cfg.Annotations.PausedAt:    time.Now().UTC().Format(time.RFC3339),
+					},
+				},
+				Spec: appsv1.DeploymentSpec{Paused: true},
+			},
+			wantExpired: false,
+			wantErr:     false,
+		},
+		{
+			name: "no paused-at annotation",
+			deploy: &appsv1.Deployment{
+				ObjectMeta: metav1.ObjectMeta{
+					Annotations: map[string]string{
+						cfg.Annotations.PausePeriod: "5m",
+					},
+				},
+			},
+			wantErr: true,
+		},
+		{
+			name: "invalid pause period",
+			deploy: &appsv1.Deployment{
+				ObjectMeta: metav1.ObjectMeta{
+					Annotations: map[string]string{
+						cfg.Annotations.PausePeriod: "invalid",
+						cfg.Annotations.PausedAt:    time.Now().UTC().Format(time.RFC3339),
+					},
+				},
+			},
+			wantErr: true,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			expired, _, err := handler.CheckPauseExpired(tt.deploy)
+			if (err != nil) != tt.wantErr {
+				t.Errorf("CheckPauseExpired() error = %v, wantErr %v", err, tt.wantErr)
+				return
+			}
+			if !tt.wantErr && expired != tt.wantExpired {
+				t.Errorf("CheckPauseExpired() expired = %v, want %v", expired, tt.wantExpired)
+			}
+		})
+	}
+}
+
+func TestPauseHandler_ClearPause(t *testing.T) {
+	cfg := config.NewDefault()
+	handler := NewPauseHandler(cfg)
+
+	deploy := &appsv1.Deployment{
+		ObjectMeta: metav1.ObjectMeta{
+			Annotations: map[string]string{
+				cfg.Annotations.PausePeriod: "5m",
+				cfg.Annotations.PausedAt:    time.Now().UTC().Format(time.RFC3339),
+			},
+		},
+		Spec: appsv1.DeploymentSpec{
+			Paused: true,
+		},
+	}
+
+	handler.ClearPause(deploy)
+
+	if deploy.Spec.Paused {
+		t.Error("Expected deployment to be unpaused")
+	}
+
+	if _, exists := deploy.Annotations[cfg.Annotations.PausedAt]; exists {
+		t.Error("Expected paused-at annotation to be removed")
+	}
+
+	// Pause period should be preserved (user's config)
+	if deploy.Annotations[cfg.Annotations.PausePeriod] != "5m" {
+		t.Error("Expected pause-period annotation to be preserved")
+	}
+}
+
+func TestPauseHandler_IsPausedByReloader(t *testing.T) {
+	cfg := config.NewDefault()
+	handler := NewPauseHandler(cfg)
+
+	tests := []struct {
+		name   string
+		deploy *appsv1.Deployment
+		want   bool
+	}{
+		{
+			name: "paused by reloader",
+			deploy: &appsv1.Deployment{
+				ObjectMeta: metav1.ObjectMeta{
+					Annotations: map[string]string{
+						cfg.Annotations.PausePeriod: "5m",
+						cfg.Annotations.PausedAt:    time.Now().UTC().Format(time.RFC3339),
+					},
+				},
+				Spec: appsv1.DeploymentSpec{Paused: true},
+			},
+			want: true,
+		},
+		{
+			name: "paused but not by reloader (no paused-at)",
+			deploy: &appsv1.Deployment{
+				ObjectMeta: metav1.ObjectMeta{
+					Annotations: map[string]string{
+						cfg.Annotations.PausePeriod: "5m",
+					},
+				},
+				Spec: appsv1.DeploymentSpec{Paused: true},
+			},
+			want: false,
+		},
+		{
+			name: "not paused",
+			deploy: &appsv1.Deployment{
+				ObjectMeta: metav1.ObjectMeta{
+					Annotations: map[string]string{
+						cfg.Annotations.PausePeriod: "5m",
+						cfg.Annotations.PausedAt:    time.Now().UTC().Format(time.RFC3339),
+					},
+				},
+				Spec: appsv1.DeploymentSpec{Paused: false},
+			},
+			want: false,
+		},
+		{
+			name: "no annotations",
+			deploy: &appsv1.Deployment{
+				Spec: appsv1.DeploymentSpec{Paused: true},
+			},
+			want: false,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			got := handler.IsPausedByReloader(tt.deploy)
+			if got != tt.want {
+				t.Errorf("IsPausedByReloader() = %v, want %v", got, tt.want)
+			}
+		})
+	}
+}
diff --git a/internal/pkg/workload/deployment.go b/internal/pkg/workload/deployment.go
index 0ddb5b45..1b5ab5f8 100644
--- a/internal/pkg/workload/deployment.go
+++ b/internal/pkg/workload/deployment.go
@@ -192,3 +192,8 @@ func (w *DeploymentWorkload) UsesSecret(name string) bool {
 func (w *DeploymentWorkload) GetOwnerReferences() []metav1.OwnerReference {
 	return w.deployment.OwnerReferences
 }
+
+// GetDeployment returns the underlying Deployment for special handling.
+func (w *DeploymentWorkload) GetDeployment() *appsv1.Deployment {
+	return w.deployment
+}
diff --git a/internal/pkg/workload/registry.go b/internal/pkg/workload/registry.go
index 55f55b2d..8525d562 100644
--- a/internal/pkg/workload/registry.go
+++ b/internal/pkg/workload/registry.go
@@ -3,6 +3,7 @@ package workload
 import (
 	"fmt"
 
+	argorolloutv1alpha1 "github.com/argoproj/argo-rollouts/pkg/apis/rollouts/v1alpha1"
 	appsv1 "k8s.io/api/apps/v1"
 	batchv1 "k8s.io/api/batch/v1"
 	"sigs.k8s.io/controller-runtime/pkg/client"
@@ -48,6 +49,11 @@ func (r *Registry) FromObject(obj client.Object) (WorkloadAccessor, error) {
 		return NewJobWorkload(o), nil
 	case *batchv1.CronJob:
 		return NewCronJobWorkload(o), nil
+	case *argorolloutv1alpha1.Rollout:
+		if !r.argoRolloutsEnabled {
+			return nil, fmt.Errorf("Argo Rollouts support is not enabled")
+		}
+		return NewRolloutWorkload(o), nil
 	default:
 		return nil, fmt.Errorf("unsupported object type: %T", obj)
 	}
diff --git a/internal/pkg/workload/rollout.go b/internal/pkg/workload/rollout.go
new file mode 100644
index 00000000..7ea9643d
--- /dev/null
+++ b/internal/pkg/workload/rollout.go
@@ -0,0 +1,274 @@
+package workload
+
+import (
+	"context"
+	"fmt"
+	"time"
+
+	argorolloutv1alpha1 "github.com/argoproj/argo-rollouts/pkg/apis/rollouts/v1alpha1"
+	corev1 "k8s.io/api/core/v1"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
+	"sigs.k8s.io/controller-runtime/pkg/client"
+)
+
+// RolloutStrategy defines how Argo Rollouts are updated.
+type RolloutStrategy string
+
+const (
+	// RolloutStrategyRollout performs a standard rollout update.
+	RolloutStrategyRollout RolloutStrategy = "rollout"
+
+	// RolloutStrategyRestart sets the restartAt field to trigger a restart.
+	RolloutStrategyRestart RolloutStrategy = "restart"
+)
+
+// RolloutStrategyAnnotation is the annotation key for specifying the rollout strategy.
+const RolloutStrategyAnnotation = "reloader.stakater.com/rollout-strategy"
+
+// RolloutWorkload wraps an Argo Rollout.
+type RolloutWorkload struct {
+	rollout *argorolloutv1alpha1.Rollout
+}
+
+// NewRolloutWorkload creates a new RolloutWorkload.
+func NewRolloutWorkload(r *argorolloutv1alpha1.Rollout) *RolloutWorkload {
+	return &RolloutWorkload{rollout: r}
+}
+
+// Ensure RolloutWorkload implements WorkloadAccessor.
+var _ WorkloadAccessor = (*RolloutWorkload)(nil)
+
+func (w *RolloutWorkload) Kind() Kind {
+	return KindArgoRollout
+}
+
+func (w *RolloutWorkload) GetObject() client.Object {
+	return w.rollout
+}
+
+func (w *RolloutWorkload) GetName() string {
+	return w.rollout.Name
+}
+
+func (w *RolloutWorkload) GetNamespace() string {
+	return w.rollout.Namespace
+}
+
+func (w *RolloutWorkload) GetAnnotations() map[string]string {
+	return w.rollout.Annotations
+}
+
+func (w *RolloutWorkload) GetPodTemplateAnnotations() map[string]string {
+	if w.rollout.Spec.Template.Annotations == nil {
+		w.rollout.Spec.Template.Annotations = make(map[string]string)
+	}
+	return w.rollout.Spec.Template.Annotations
+}
+
+func (w *RolloutWorkload) SetPodTemplateAnnotation(key, value string) {
+	if w.rollout.Spec.Template.Annotations == nil {
+		w.rollout.Spec.Template.Annotations = make(map[string]string)
+	}
+	w.rollout.Spec.Template.Annotations[key] = value
+}
+
+func (w *RolloutWorkload) GetContainers() []corev1.Container {
+	return w.rollout.Spec.Template.Spec.Containers
+}
+
+func (w *RolloutWorkload) SetContainers(containers []corev1.Container) {
+	w.rollout.Spec.Template.Spec.Containers = containers
+}
+
+func (w *RolloutWorkload) GetInitContainers() []corev1.Container {
+	return w.rollout.Spec.Template.Spec.InitContainers
+}
+
+func (w *RolloutWorkload) SetInitContainers(containers []corev1.Container) {
+	w.rollout.Spec.Template.Spec.InitContainers = containers
+}
+
+func (w *RolloutWorkload) GetVolumes() []corev1.Volume {
+	return w.rollout.Spec.Template.Spec.Volumes
+}
+
+// Update updates the Rollout. It uses the rollout strategy annotation to determine
+// whether to do a standard rollout or set the restartAt field.
+func (w *RolloutWorkload) Update(ctx context.Context, c client.Client) error {
+	strategy := w.getStrategy()
+	switch strategy {
+	case RolloutStrategyRestart:
+		// Use merge patch to set restartAt field
+		restartAt := metav1.NewTime(time.Now())
+		w.rollout.Spec.RestartAt = &restartAt
+	}
+	// For both strategies, we update the rollout (annotations have already been set)
+	return c.Update(ctx, w.rollout)
+}
+
+// getStrategy returns the rollout strategy from the annotation.
+func (w *RolloutWorkload) getStrategy() RolloutStrategy {
+	annotations := w.rollout.GetAnnotations()
+	if annotations == nil {
+		return RolloutStrategyRollout
+	}
+	strategy := annotations[RolloutStrategyAnnotation]
+	switch RolloutStrategy(strategy) {
+	case RolloutStrategyRestart:
+		return RolloutStrategyRestart
+	default:
+		return RolloutStrategyRollout
+	}
+}
+
+func (w *RolloutWorkload) DeepCopy() Workload {
+	return &RolloutWorkload{rollout: w.rollout.DeepCopy()}
+}
+
+func (w *RolloutWorkload) GetEnvFromSources() []corev1.EnvFromSource {
+	var sources []corev1.EnvFromSource
+	for _, container := range w.rollout.Spec.Template.Spec.Containers {
+		sources = append(sources, container.EnvFrom...)
+	}
+	for _, container := range w.rollout.Spec.Template.Spec.InitContainers {
+		sources = append(sources, container.EnvFrom...)
+	}
+	return sources
+}
+
+func (w *RolloutWorkload) UsesConfigMap(name string) bool {
+	spec := &w.rollout.Spec.Template.Spec
+
+	// Check volumes
+	for _, vol := range spec.Volumes {
+		if vol.ConfigMap != nil && vol.ConfigMap.Name == name {
+			return true
+		}
+		if vol.Projected != nil {
+			for _, source := range vol.Projected.Sources {
+				if source.ConfigMap != nil && source.ConfigMap.Name == name {
+					return true
+				}
+			}
+		}
+	}
+
+	// Check containers
+	for _, container := range spec.Containers {
+		for _, envFrom := range container.EnvFrom {
+			if envFrom.ConfigMapRef != nil && envFrom.ConfigMapRef.Name == name {
+				return true
+			}
+		}
+		for _, env := range container.Env {
+			if env.ValueFrom != nil && env.ValueFrom.ConfigMapKeyRef != nil && env.ValueFrom.ConfigMapKeyRef.Name == name {
+				return true
+			}
+		}
+	}
+
+	// Check init containers
+	for _, container := range spec.InitContainers {
+		for _, envFrom := range container.EnvFrom {
+			if envFrom.ConfigMapRef != nil && envFrom.ConfigMapRef.Name == name {
+				return true
+			}
+		}
+		for _, env := range container.Env {
+			if env.ValueFrom != nil && env.ValueFrom.ConfigMapKeyRef != nil && env.ValueFrom.ConfigMapKeyRef.Name == name {
+				return true
+			}
+		}
+	}
+
+	return false
+}
+
+func (w *RolloutWorkload) UsesSecret(name string) bool {
+	spec := &w.rollout.Spec.Template.Spec
+
+	// Check volumes
+	for _, vol := range spec.Volumes {
+		if vol.Secret != nil && vol.Secret.SecretName == name {
+			return true
+		}
+		if vol.Projected != nil {
+			for _, source := range vol.Projected.Sources {
+				if source.Secret != nil && source.Secret.Name == name {
+					return true
+				}
+			}
+		}
+	}
+
+	// Check containers
+	for _, container := range spec.Containers {
+		for _, envFrom := range container.EnvFrom {
+			if envFrom.SecretRef != nil && envFrom.SecretRef.Name == name {
+				return true
+			}
+		}
+		for _, env := range container.Env {
+			if env.ValueFrom != nil && env.ValueFrom.SecretKeyRef != nil && env.ValueFrom.SecretKeyRef.Name == name {
+				return true
+			}
+		}
+	}
+
+	// Check init containers
+	for _, container := range spec.InitContainers {
+		for _, envFrom := range container.EnvFrom {
+			if envFrom.SecretRef != nil && envFrom.SecretRef.Name == name {
+				return true
+			}
+		}
+		for _, env := range container.Env {
+			if env.ValueFrom != nil && env.ValueFrom.SecretKeyRef != nil && env.ValueFrom.SecretKeyRef.Name == name {
+				return true
+			}
+		}
+	}
+
+	return false
+}
+
+func (w *RolloutWorkload) GetOwnerReferences() []metav1.OwnerReference {
+	return w.rollout.OwnerReferences
+}
+
+// GetRollout returns the underlying Rollout for special handling.
+func (w *RolloutWorkload) GetRollout() *argorolloutv1alpha1.Rollout {
+	return w.rollout
+}
+
+// GetStrategy returns the configured rollout strategy.
+func (w *RolloutWorkload) GetStrategy() RolloutStrategy {
+	return w.getStrategy()
+}
+
+// String returns a string representation of the strategy.
+func (s RolloutStrategy) String() string {
+	return string(s)
+}
+
+// ToRolloutStrategy converts a string to RolloutStrategy.
+func ToRolloutStrategy(s string) RolloutStrategy {
+	switch RolloutStrategy(s) {
+	case RolloutStrategyRestart:
+		return RolloutStrategyRestart
+	case RolloutStrategyRollout:
+		return RolloutStrategyRollout
+	default:
+		return RolloutStrategyRollout
+	}
+}
+
+// Validate checks if the rollout strategy is valid.
+func (s RolloutStrategy) Validate() error {
+	switch s {
+	case RolloutStrategyRollout, RolloutStrategyRestart:
+		return nil
+	default:
+		return fmt.Errorf("invalid rollout strategy: %s", s)
+	}
+}
diff --git a/internal/pkg/workload/workload_test.go b/internal/pkg/workload/workload_test.go
index b7cb2510..b616e0c6 100644
--- a/internal/pkg/workload/workload_test.go
+++ b/internal/pkg/workload/workload_test.go
@@ -3,6 +3,7 @@ package workload
 import (
 	"testing"
 
+	argorolloutv1alpha1 "github.com/argoproj/argo-rollouts/pkg/apis/rollouts/v1alpha1"
 	appsv1 "k8s.io/api/apps/v1"
 	corev1 "k8s.io/api/core/v1"
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
@@ -691,4 +692,226 @@ func TestWorkloadInterface(t *testing.T) {
 	var _ WorkloadAccessor = (*DeploymentWorkload)(nil)
 	var _ WorkloadAccessor = (*DaemonSetWorkload)(nil)
 	var _ WorkloadAccessor = (*StatefulSetWorkload)(nil)
+	var _ WorkloadAccessor = (*RolloutWorkload)(nil)
+}
+
+// RolloutWorkload tests
+func TestRolloutWorkload_BasicGetters(t *testing.T) {
+	rollout := &argorolloutv1alpha1.Rollout{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      "test-rollout",
+			Namespace: "test-ns",
+			Annotations: map[string]string{
+				"key": "value",
+			},
+		},
+	}
+
+	w := NewRolloutWorkload(rollout)
+
+	if w.Kind() != KindArgoRollout {
+		t.Errorf("Kind() = %v, want %v", w.Kind(), KindArgoRollout)
+	}
+	if w.GetName() != "test-rollout" {
+		t.Errorf("GetName() = %v, want test-rollout", w.GetName())
+	}
+	if w.GetNamespace() != "test-ns" {
+		t.Errorf("GetNamespace() = %v, want test-ns", w.GetNamespace())
+	}
+	if w.GetAnnotations()["key"] != "value" {
+		t.Errorf("GetAnnotations()[key] = %v, want value", w.GetAnnotations()["key"])
+	}
+	if w.GetObject() != rollout {
+		t.Error("GetObject() should return the underlying rollout")
+	}
+}
+
+func TestRolloutWorkload_PodTemplateAnnotations(t *testing.T) {
+	rollout := &argorolloutv1alpha1.Rollout{
+		ObjectMeta: metav1.ObjectMeta{Name: "test"},
+		Spec: argorolloutv1alpha1.RolloutSpec{
+			Template: corev1.PodTemplateSpec{
+				ObjectMeta: metav1.ObjectMeta{
+					Annotations: map[string]string{
+						"existing": "annotation",
+					},
+				},
+			},
+		},
+	}
+
+	w := NewRolloutWorkload(rollout)
+
+	// Test get
+	annotations := w.GetPodTemplateAnnotations()
+	if annotations["existing"] != "annotation" {
+		t.Errorf("GetPodTemplateAnnotations()[existing] = %v, want annotation", annotations["existing"])
+	}
+
+	// Test set
+	w.SetPodTemplateAnnotation("new-key", "new-value")
+	if w.GetPodTemplateAnnotations()["new-key"] != "new-value" {
+		t.Error("SetPodTemplateAnnotation should add new annotation")
+	}
+}
+
+func TestRolloutWorkload_GetStrategy_Default(t *testing.T) {
+	rollout := &argorolloutv1alpha1.Rollout{
+		ObjectMeta: metav1.ObjectMeta{Name: "test"},
+	}
+
+	w := NewRolloutWorkload(rollout)
+
+	if w.GetStrategy() != RolloutStrategyRollout {
+		t.Errorf("GetStrategy() = %v, want %v (default)", w.GetStrategy(), RolloutStrategyRollout)
+	}
+}
+
+func TestRolloutWorkload_GetStrategy_Restart(t *testing.T) {
+	rollout := &argorolloutv1alpha1.Rollout{
+		ObjectMeta: metav1.ObjectMeta{
+			Name: "test",
+			Annotations: map[string]string{
+				RolloutStrategyAnnotation: "restart",
+			},
+		},
+	}
+
+	w := NewRolloutWorkload(rollout)
+
+	if w.GetStrategy() != RolloutStrategyRestart {
+		t.Errorf("GetStrategy() = %v, want %v", w.GetStrategy(), RolloutStrategyRestart)
+	}
+}
+
+func TestRolloutWorkload_UsesConfigMap_Volume(t *testing.T) {
+	rollout := &argorolloutv1alpha1.Rollout{
+		ObjectMeta: metav1.ObjectMeta{Name: "test"},
+		Spec: argorolloutv1alpha1.RolloutSpec{
+			Template: corev1.PodTemplateSpec{
+				Spec: corev1.PodSpec{
+					Volumes: []corev1.Volume{
+						{
+							Name: "config-vol",
+							VolumeSource: corev1.VolumeSource{
+								ConfigMap: &corev1.ConfigMapVolumeSource{
+									LocalObjectReference: corev1.LocalObjectReference{
+										Name: "rollout-config",
+									},
+								},
+							},
+						},
+					},
+				},
+			},
+		},
+	}
+
+	w := NewRolloutWorkload(rollout)
+
+	if !w.UsesConfigMap("rollout-config") {
+		t.Error("Rollout UsesConfigMap should return true for ConfigMap volume")
+	}
+	if w.UsesConfigMap("other-config") {
+		t.Error("Rollout UsesConfigMap should return false for non-existent ConfigMap")
+	}
+}
+
+func TestRolloutWorkload_UsesSecret_EnvFrom(t *testing.T) {
+	rollout := &argorolloutv1alpha1.Rollout{
+		ObjectMeta: metav1.ObjectMeta{Name: "test"},
+		Spec: argorolloutv1alpha1.RolloutSpec{
+			Template: corev1.PodTemplateSpec{
+				Spec: corev1.PodSpec{
+					Containers: []corev1.Container{
+						{
+							Name: "main",
+							EnvFrom: []corev1.EnvFromSource{
+								{
+									SecretRef: &corev1.SecretEnvSource{
+										LocalObjectReference: corev1.LocalObjectReference{
+											Name: "rollout-secret",
+										},
+									},
+								},
+							},
+						},
+					},
+				},
+			},
+		},
+	}
+
+	w := NewRolloutWorkload(rollout)
+
+	if !w.UsesSecret("rollout-secret") {
+		t.Error("Rollout UsesSecret should return true for Secret envFrom")
+	}
+	if w.UsesSecret("other-secret") {
+		t.Error("Rollout UsesSecret should return false for non-existent Secret")
+	}
+}
+
+func TestRolloutWorkload_DeepCopy(t *testing.T) {
+	rollout := &argorolloutv1alpha1.Rollout{
+		ObjectMeta: metav1.ObjectMeta{Name: "test"},
+		Spec: argorolloutv1alpha1.RolloutSpec{
+			Template: corev1.PodTemplateSpec{
+				ObjectMeta: metav1.ObjectMeta{
+					Annotations: map[string]string{
+						"original": "value",
+					},
+				},
+			},
+		},
+	}
+
+	w := NewRolloutWorkload(rollout)
+	copy := w.DeepCopy()
+
+	// Verify copy is independent
+	w.SetPodTemplateAnnotation("modified", "true")
+
+	copyAnnotations := copy.(*RolloutWorkload).GetPodTemplateAnnotations()
+	if copyAnnotations["modified"] == "true" {
+		t.Error("DeepCopy should create independent copy")
+	}
+}
+
+func TestRolloutStrategy_Validate(t *testing.T) {
+	tests := []struct {
+		strategy RolloutStrategy
+		wantErr  bool
+	}{
+		{RolloutStrategyRollout, false},
+		{RolloutStrategyRestart, false},
+		{RolloutStrategy("invalid"), true},
+		{RolloutStrategy(""), true},
+	}
+
+	for _, tt := range tests {
+		err := tt.strategy.Validate()
+		if (err != nil) != tt.wantErr {
+			t.Errorf("Validate(%s) error = %v, wantErr %v", tt.strategy, err, tt.wantErr)
+		}
+	}
+}
+
+func TestToRolloutStrategy(t *testing.T) {
+	tests := []struct {
+		input    string
+		expected RolloutStrategy
+	}{
+		{"rollout", RolloutStrategyRollout},
+		{"restart", RolloutStrategyRestart},
+		{"invalid", RolloutStrategyRollout}, // defaults to rollout
+		{"", RolloutStrategyRollout},        // defaults to rollout
+	}
+
+	for _, tt := range tests {
+		result := ToRolloutStrategy(tt.input)
+		if result != tt.expected {
+			t.Errorf("ToRolloutStrategy(%s) = %v, want %v", tt.input, result, tt.expected)
+		}
+	}
 }