diff --git a/api/gen/proto/go/usageevents/v1/usageevents.pb.go b/api/gen/proto/go/usageevents/v1/usageevents.pb.go
index 7a584d16fcc..49c2efbd29d 100644
--- a/api/gen/proto/go/usageevents/v1/usageevents.pb.go
+++ b/api/gen/proto/go/usageevents/v1/usageevents.pb.go
@@ -209,6 +209,7 @@ const (
 	CTA_CTA_PREMIUM_SUPPORT CTA = 4
 	CTA_CTA_TRUSTED_DEVICES CTA = 5
 	CTA_CTA_UPGRADE_BANNER  CTA = 6
+	CTA_CTA_BILLING_SUMMARY CTA = 7
 )
 
 var CTA_name = map[int32]string{
@@ -219,6 +220,7 @@ var CTA_name = map[int32]string{
 	4: "CTA_PREMIUM_SUPPORT",
 	5: "CTA_TRUSTED_DEVICES",
 	6: "CTA_UPGRADE_BANNER",
+	7: "CTA_BILLING_SUMMARY",
 }
 
 var CTA_value = map[string]int32{
@@ -229,6 +231,7 @@ var CTA_value = map[string]int32{
 	"CTA_PREMIUM_SUPPORT": 4,
 	"CTA_TRUSTED_DEVICES": 5,
 	"CTA_UPGRADE_BANNER":  6,
+	"CTA_BILLING_SUMMARY": 7,
 }
 
 func (x CTA) String() string {
@@ -2812,188 +2815,189 @@ func init() {
 }
 
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+	0xcc, 0x21, 0xbe, 0xa9, 0x8a, 0x48, 0xc3, 0xda, 0x96, 0xce, 0xdf, 0x84, 0x6f, 0x81, 0x47, 0x59,
+	0xc1, 0xd4, 0xc4, 0x1d, 0xa4, 0x09, 0xa2, 0x32, 0xb6, 0xcf, 0x2d, 0xe7, 0xe4, 0x7e, 0xbc, 0x37,
+	0x0a, 0x7a, 0x43, 0xc0, 0xfc, 0x4a, 0xce, 0x9a, 0xc2, 0x2d, 0xed, 0xf9, 0x56, 0x43, 0xd8, 0x91,
+	0xf9, 0xd5, 0x19, 0xfd, 0x6a, 0x62, 0xca, 0xbb, 0x12, 0x26, 0x6d, 0xa4, 0x7d, 0x63, 0x97, 0xaf,
+	0xcd, 0x48, 0xc5, 0x34, 0x5a, 0x51, 0xb7, 0x15, 0x22, 0x3c, 0x13, 0xd4, 0x86, 0x50, 0x57, 0x1b,
+	0xaa, 0xbe, 0xcb, 0xaf, 0xc1, 0xb7, 0xc1, 0x1b, 0x39, 0x56, 0x6c, 0x85, 0xa8, 0x22, 0x41, 0xf2,
+	0xb6, 0x8a, 0x75, 0xc4, 0xb6, 0x4e, 0xfe, 0xd6, 0xfa, 0x2f, 0x38, 0x30, 0x3f, 0xfa, 0xef, 0x97,
+	0x70, 0x19, 0xdc, 0x48, 0xfa, 0xc2, 0xba, 0xa0, 0x77, 0xf0, 0xd8, 0x59, 0x77, 0x03, 0x5c, 0x1b,
+	0x07, 0xe0, 0x8e, 0x28, 0x06, 0xcb, 0x9a, 0x9b, 0xda, 0xb8, 0xa3, 0xb6, 0xdb, 0xb2, 0xc4, 0x97,
+	0xe1, 0x02, 0xb8, 0x32, 0xde, 0x28, 0x23, 0xa4, 0x21, 0xbe, 0x32, 0xcd, 0x4e, 0xa8, 0x6b, 0x88,
+	0x1d, 0x5b, 0xeb, 0xbf, 0xe7, 0x40, 0x45, 0xd4, 0x05, 0x78, 0x09, 0x5c, 0x10, 0x75, 0x61, 0x8c,
+	0xce, 0x55, 0x00, 0x83, 0x97, 0x42, 0x47, 0x57, 0x88, 0xa8, 0xb5, 0x5a, 0xb2, 0xa8, 0x6b, 0xc1,
+	0xa1, 0x7b, 0x0d, 0x5c, 0x62, 0xef, 0x45, 0x5d, 0x7d, 0x16, 0x9c, 0xc5, 0x18, 0xab, 0x5a, 0x2b,
+	0x38, 0x6b, 0x93, 0x86, 0x80, 0x32, 0x41, 0xf2, 0x7b, 0x1d, 0x19, 0xeb, 0x98, 0xaf, 0xc4, 0x0d,
+	0x6d, 0x24, 0x37, 0xd5, 0x4e, 0x93, 0xe0, 0x4e, 0xbb, 0xad, 0x21, 0x9d, 0x3f, 0x11, 0x37, 0xe8,
+	0x28, 0xc8, 0x7f, 0x89, 0x48, 0xf2, 0x33, 0x35, 0xd8, 0x38, 0x4e, 0xc6, 0x63, 0x77, 0xda, 0xdb,
+	0x48, 0x90, 0x64, 0x52, 0x17, 0x5a, 0x2d, 0x19, 0xf1, 0xa7, 0x62, 0x83, 0xba, 0xda, 0x68, 0xa8,
+	0xad, 0x6d, 0x82, 0x3b, 0xcd, 0xa6, 0x80, 0x76, 0xf9, 0xd3, 0xeb, 0x7f, 0xaa, 0x80, 0x2b, 0x53,
+	0x3f, 0x51, 0x05, 0x1b, 0x9c, 0xda, 0xd2, 0xe5, 0xed, 0x30, 0x34, 0x44, 0x6e, 0x21, 0xad, 0xd1,
+	0x20, 0x3b, 0x6a, 0x4b, 0x1a, 0x9b, 0xef, 0x2a, 0x58, 0x9a, 0x05, 0xc4, 0x0d, 0x41, 0xdc, 0xe1,
+	0x39, 0x78, 0x0b, 0xac, 0xcc, 0x82, 0x08, 0xcf, 0x31, 0x09, 0x6e, 0xf1, 0x7c, 0x39, 0x38, 0x32,
+	0x67, 0xa1, 0xda, 0xc2, 0xb6, 0x8c, 0xa4, 0x8e, 0xbe, 0xcb, 0x57, 0xb2, 0xc6, 0x93, 0x9b, 0x82,
+	0xda, 0xe0, 0x4f, 0x04, 0xf7, 0x9b, 0x59, 0x90, 0xa7, 0x2a, 0x12, 0xf8, 0x93, 0x70, 0x0d, 0x2c,
+	0xcf, 0x42, 0xb0, 0xb0, 0x23, 0x89, 0x3f, 0x15, 0x5c, 0x09, 0x66, 0x81, 0x9a, 0x82, 0xae, 0xcb,
+	0xa8, 0xa9, 0x61, 0x9d, 0x3f, 0x9d, 0x35, 0xbd, 0x26, 0x26, 0xba, 0x2c, 0x34, 0x31, 0x3f, 0x97,
+	0x85, 0xd2, 0xda, 0x78, 0x5b, 0x6e, 0xa9, 0x32, 0x7f, 0x26, 0x8b, 0xba, 0xb6, 0xa3, 0x0b, 0x3c,
+	0xc8, 0x9c, 0x9c, 0xd0, 0xdc, 0xe2, 0xcf, 0xd6, 0x3f, 0xf8, 0xc3, 0xe7, 0x37, 0xb9, 0x3f, 0x7e,
+	0x7e, 0x93, 0xfb, 0xf3, 0xe7, 0x37, 0xb9, 0xf7, 0xb5, 0x3d, 0xd3, 0xff, 0x70, 0xf0, 0x62, 0xa3,
+	0xeb, 0xec, 0x6f, 0xee, 0xb9, 0xc6, 0x81, 0x19, 0xd6, 0x6a, 0x86, 0xb5, 0x99, 0xfc, 0x68, 0xc0,
+	0xe8, 0x9b, 0x9b, 0x7b, 0xd4, 0xde, 0x64, 0xbf, 0x10, 0xd8, 0xdc, 0x73, 0xc6, 0x7e, 0x45, 0xf0,
+	0x24, 0xf5, 0x78, 0xf0, 0xf0, 0xc5, 0x29, 0x06, 0x7b, 0xe3, 0xdf, 0x01, 0x00, 0x00, 0xff, 0xff,
+	0x6d, 0xa4, 0x17, 0x19, 0x75, 0x30, 0x00, 0x00,
 }
 
 func (m *UIBannerClickEvent) Marshal() (dAtA []byte, err error) {
diff --git a/api/proto/teleport/usageevents/v1/usageevents.proto b/api/proto/teleport/usageevents/v1/usageevents.proto
index b31542a4f7b..6a9d16efc88 100644
--- a/api/proto/teleport/usageevents/v1/usageevents.proto
+++ b/api/proto/teleport/usageevents/v1/usageevents.proto
@@ -211,6 +211,7 @@ enum CTA {
   CTA_PREMIUM_SUPPORT = 4;
   CTA_TRUSTED_DEVICES = 5;
   CTA_UPGRADE_BANNER = 6;
+  CTA_BILLING_SUMMARY = 7;
 }
 
 // UIDiscoverDeployServiceEvent is emitted after the user installs a Teleport Agent.
diff --git a/gen/proto/go/prehog/v1alpha/prehogv1alphaconnect/teleport.connect.go b/gen/proto/go/prehog/v1alpha/prehogv1alphaconnect/teleport.connect.go
index e63a771bda3..0c9cae98966 100644
--- a/gen/proto/go/prehog/v1alpha/prehogv1alphaconnect/teleport.connect.go
+++ b/gen/proto/go/prehog/v1alpha/prehogv1alphaconnect/teleport.connect.go
@@ -61,8 +61,19 @@ const (
 // TeleportReportingServiceClient is a client for the prehog.v1alpha.TeleportReportingService
 // service.
 type TeleportReportingServiceClient interface {
+	// equivalent to SubmitEvents with a single event, should be unused by now
+	//
 	// Deprecated: do not use.
 	SubmitEvent(context.Context, *connect_go.Request[v1alpha.SubmitEventRequest]) (*connect_go.Response[v1alpha.SubmitEventResponse], error)
+	// encodes and forwards usage events to the PostHog event database; each
+	// event is annotated with some properties that depend on the identity of the
+	// caller:
+	//   - tp.account_id (UUID in string form, can be empty if missing from the
+	//     license)
+	//   - tp.license_name (should always be a UUID)
+	//   - tp.license_authority (name of the authority that signed the license file
+	//     used for authentication)
+	//   - tp.is_cloud (boolean)
 	SubmitEvents(context.Context, *connect_go.Request[v1alpha.SubmitEventsRequest]) (*connect_go.Response[v1alpha.SubmitEventsResponse], error)
 	HelloTeleport(context.Context, *connect_go.Request[v1alpha.HelloTeleportRequest]) (*connect_go.Response[v1alpha.HelloTeleportResponse], error)
 }
@@ -122,8 +133,19 @@ func (c *teleportReportingServiceClient) HelloTeleport(ctx context.Context, req
 // TeleportReportingServiceHandler is an implementation of the
 // prehog.v1alpha.TeleportReportingService service.
 type TeleportReportingServiceHandler interface {
+	// equivalent to SubmitEvents with a single event, should be unused by now
+	//
 	// Deprecated: do not use.
 	SubmitEvent(context.Context, *connect_go.Request[v1alpha.SubmitEventRequest]) (*connect_go.Response[v1alpha.SubmitEventResponse], error)
+	// encodes and forwards usage events to the PostHog event database; each
+	// event is annotated with some properties that depend on the identity of the
+	// caller:
+	//   - tp.account_id (UUID in string form, can be empty if missing from the
+	//     license)
+	//   - tp.license_name (should always be a UUID)
+	//   - tp.license_authority (name of the authority that signed the license file
+	//     used for authentication)
+	//   - tp.is_cloud (boolean)
 	SubmitEvents(context.Context, *connect_go.Request[v1alpha.SubmitEventsRequest]) (*connect_go.Response[v1alpha.SubmitEventsResponse], error)
 	HelloTeleport(context.Context, *connect_go.Request[v1alpha.HelloTeleportRequest]) (*connect_go.Response[v1alpha.HelloTeleportResponse], error)
 }
diff --git a/gen/proto/go/prehog/v1alpha/teleport.pb.go b/gen/proto/go/prehog/v1alpha/teleport.pb.go
index fd63f352304..5a88c93e684 100644
--- a/gen/proto/go/prehog/v1alpha/teleport.pb.go
+++ b/gen/proto/go/prehog/v1alpha/teleport.pb.go
@@ -40,13 +40,22 @@ const (
 type ResourceKind int32
 
 const (
-	ResourceKind_RESOURCE_KIND_UNSPECIFIED     ResourceKind = 0
-	ResourceKind_RESOURCE_KIND_NODE            ResourceKind = 1
-	ResourceKind_RESOURCE_KIND_APP_SERVER      ResourceKind = 2
-	ResourceKind_RESOURCE_KIND_KUBE_SERVER     ResourceKind = 3
-	ResourceKind_RESOURCE_KIND_DB_SERVER       ResourceKind = 4
+	ResourceKind_RESOURCE_KIND_UNSPECIFIED ResourceKind = 0
+	// PostHog property value: "node"
+	ResourceKind_RESOURCE_KIND_NODE ResourceKind = 1
+	// PostHog property value: "app_server"
+	ResourceKind_RESOURCE_KIND_APP_SERVER ResourceKind = 2
+	// PostHog property value: "kube_server"
+	ResourceKind_RESOURCE_KIND_KUBE_SERVER ResourceKind = 3
+	// PostHog property value: "db_server"
+	ResourceKind_RESOURCE_KIND_DB_SERVER ResourceKind = 4
+	// PostHog property value: "windows_desktop"
 	ResourceKind_RESOURCE_KIND_WINDOWS_DESKTOP ResourceKind = 5
-	ResourceKind_RESOURCE_KIND_NODE_OPENSSH    ResourceKind = 6
+	// ServerV3 ("node") heartbeat with a subkind of "openssh" (as opposed to
+	// empty or "teleport"); not used in keepalives
+	//
+	// PostHog property value: "node.openssh"
+	ResourceKind_RESOURCE_KIND_NODE_OPENSSH ResourceKind = 6
 )
 
 // Enum value maps for ResourceKind.
@@ -324,6 +333,7 @@ const (
 	CTA_CTA_PREMIUM_SUPPORT CTA = 4
 	CTA_CTA_TRUSTED_DEVICES CTA = 5
 	CTA_CTA_UPGRADE_BANNER  CTA = 6
+	CTA_CTA_BILLING_SUMMARY CTA = 7
 )
 
 // Enum value maps for CTA.
@@ -336,6 +346,7 @@ var (
 		4: "CTA_PREMIUM_SUPPORT",
 		5: "CTA_TRUSTED_DEVICES",
 		6: "CTA_UPGRADE_BANNER",
+		7: "CTA_BILLING_SUMMARY",
 	}
 	CTA_value = map[string]int32{
 		"CTA_UNSPECIFIED":     0,
@@ -345,6 +356,7 @@ var (
 		"CTA_PREMIUM_SUPPORT": 4,
 		"CTA_TRUSTED_DEVICES": 5,
 		"CTA_UPGRADE_BANNER":  6,
+		"CTA_BILLING_SUMMARY": 7,
 	}
 )
 
@@ -453,16 +465,29 @@ func (IntegrationEnrollKind) EnumDescriptor() ([]byte, []int) {
 	return file_prehog_v1alpha_teleport_proto_rawDescGZIP(), []int{4}
 }
 
+// a successful user login
+//
+// PostHog event: tp.user.login
 type UserLoginEvent struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields
 
-	// anonymized
+	// anonymized Teleport username, 32 bytes (HMAC-SHA-256) encoded in base64;
+	// should always be a real user as bots and service accounts with long-term
+	// credentials don't ever login
+	//
+	// PostHog property: tp.user_name
 	UserName string `protobuf:"bytes,1,opt,name=user_name,json=userName,proto3" json:"user_name,omitempty"`
-	// local/github/saml/oidc
+	// type of the auth connector used in the login, should be
+	// "local"/"github"/"saml"/"oidc"
+	//
+	// PostHog property: tp.connector_type
 	ConnectorType string `protobuf:"bytes,2,opt,name=connector_type,json=connectorType,proto3" json:"connector_type,omitempty"`
-	// The anonymized device ID, for logins where device trust is enabled.
+	// anonymized device ID, empty or 32 bytes (HMAC-SHA-256) encoded in base64;
+	// for logins where device trust is enabled
+	//
+	// PostHog property: tp.device_id
 	DeviceId string `protobuf:"bytes,3,opt,name=device_id,json=deviceId,proto3" json:"device_id,omitempty"`
 }
 
@@ -618,15 +643,27 @@ func (x *ResourceCreateEvent) GetResourceType() string {
 
 // a heartbeat for a resource served by a Teleport instance outside of the
 // control plane (i.e. not auth, not proxy)
+//
+// PostHog event: tp.resource.hb
 type ResourceHeartbeatEvent struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields
 
-	// anonymized, 32 bytes (HMAC-SHA-256)
-	ResourceName []byte       `protobuf:"bytes,1,opt,name=resource_name,json=resourceName,proto3" json:"resource_name,omitempty"`
+	// anonymized name of the resource, 32 bytes (HMAC-SHA-256); the name is the
+	// host ID for nodes but the actual user-facing name for other resources, so
+	// an app or a database served by multiple agents won't be counted multiple
+	// times
+	//
+	// PreHog property: tp.resource_name (in base64)
+	ResourceName []byte `protobuf:"bytes,1,opt,name=resource_name,json=resourceName,proto3" json:"resource_name,omitempty"`
+	// kind of the resource (node, app, db)
+	//
+	// PostHog property: tp.resource_type (as a string, see ResourceKind)
 	ResourceKind ResourceKind `protobuf:"varint,2,opt,name=resource_kind,json=resourceKind,proto3,enum=prehog.v1alpha.ResourceKind" json:"resource_kind,omitempty"`
 	// true if the heartbeat has no expiration
+	//
+	// PostHog property: tp.is_static
 	Static bool `protobuf:"varint,3,opt,name=static,proto3" json:"static,omitempty"`
 }
 
@@ -683,14 +720,32 @@ func (x *ResourceHeartbeatEvent) GetStatic() bool {
 	return false
 }
 
+// an event representing one of several audit events: session.start, port,
+// app.session.start, db.session.start, windows.desktop.session.start; i.e. a
+// SSH shell or port-forward, kubectl exec or kubectl port-forward, DB, App or
+// Desktop connection
+//
+// an earlier encoding (as "tp.session.start") mixed SSH sessions and kubectl
+// execs under a session type of "ssh"
+//
+// PostHog event: tp.session.start
 type SessionStartEvent struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields
 
-	// anonymized
+	// anonymized Teleport username, 32 bytes (HMAC-SHA-256) encoded in base64
+	//
+	// PostHog property: tp.user_name
 	UserName string `protobuf:"bytes,1,opt,name=user_name,json=userName,proto3" json:"user_name,omitempty"`
-	// ssh/kube/desktop, maybe db?
+	// type of the session, should be "ssh"/"k8s"/"db"/"app"/"desktop" (matching
+	// the values for api/types.SessionKind) or "app_tcp", "ssh_port_v2" or
+	// "k8s_port" for TCP Application Access connections, SSH port forwards and
+	// kubectl port-forward respectively; a type of "ssh_port" represents either a
+	// SSH port forwarding connection or a kubectl port-forward (not used in new
+	// events)
+	//
+	// PostHog property: tp.session_type
 	SessionType string `protobuf:"bytes,2,opt,name=session_type,json=sessionType,proto3" json:"session_type,omitempty"`
 }
 
@@ -740,25 +795,37 @@ func (x *SessionStartEvent) GetSessionType() string {
 	return ""
 }
 
+// the issuance of a user certificate from the user CA
+//
+// PostHog event: tp.certificate.issued
 type UserCertificateIssuedEvent struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields
 
-	// The anonymized username/principal of the entity that requested the
-	// certificate.
+	// anonymized Teleport username, 32 bytes (HMAC-SHA-256) encoded in base64; it
+	// can be the username of a bot user rather than of a regular user
+	//
+	// PostHog property: tp.user_name
 	UserName string `protobuf:"bytes,1,opt,name=user_name,json=userName,proto3" json:"user_name,omitempty"`
-	// The issued certificate TTL.
+	// the TTL of the issued certificate, typically 8 or 12 hours
+	//
+	// PostHog property: tp.ttl_minutes (in minutes, rounded up)
 	Ttl *durationpb.Duration `protobuf:"bytes,2,opt,name=ttl,proto3" json:"ttl,omitempty"`
 	// If true, the certificate was requested by a bot (i.e. Machine ID) user.
+	// PostHog property: tp.is_bot
 	IsBot bool `protobuf:"varint,3,opt,name=is_bot,json=isBot,proto3" json:"is_bot,omitempty"`
 	// If true, the certificate usage is restricted to database access.
+	// PostHog property: tp.usage_database
 	UsageDatabase bool `protobuf:"varint,4,opt,name=usage_database,json=usageDatabase,proto3" json:"usage_database,omitempty"`
 	// If true, the certificate usage is restricted to app access.
+	// PostHog property: tp.usage_app
 	UsageApp bool `protobuf:"varint,5,opt,name=usage_app,json=usageApp,proto3" json:"usage_app,omitempty"`
 	// If true, the certificate usage is restricted to Kubernetes access.
+	// PostHog property: tp.usage_kubernetes
 	UsageKubernetes bool `protobuf:"varint,6,opt,name=usage_kubernetes,json=usageKubernetes,proto3" json:"usage_kubernetes,omitempty"`
 	// If true, the certificate usage is restricted to desktop access.
+	// PostHog property: tp.usage_desktop
 	UsageDesktop bool `protobuf:"varint,7,opt,name=usage_desktop,json=usageDesktop,proto3" json:"usage_desktop,omitempty"`
 }
 
@@ -2700,12 +2767,18 @@ func (x *UICallToActionClickEvent) GetCta() CTA {
 	return CTA_CTA_UNSPECIFIED
 }
 
+// a request forwarded to a kube cluster's API server (other than exec and
+// port-forward)
+//
+// PostHog event: tp.kube.request
 type KubeRequestEvent struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields
 
-	// anonymized
+	// anonymized Teleport username, 32 bytes (HMAC-SHA-256) encoded in base64
+	//
+	// PostHog property: tp.user_name
 	UserName string `protobuf:"bytes,1,opt,name=user_name,json=userName,proto3" json:"user_name,omitempty"`
 }
 
@@ -2748,12 +2821,17 @@ func (x *KubeRequestEvent) GetUserName() string {
 	return ""
 }
 
+// an sftp event, represents a single operation on a file
+//
+// PostHog event: tp.sftp
 type SFTPEvent struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields
 
-	// anonymized
+	// anonymized Teleport username, 32 bytes (HMAC-SHA-256) encoded in base64
+	//
+	// PostHog property: tp.user_name
 	UserName string `protobuf:"bytes,1,opt,name=user_name,json=userName,proto3" json:"user_name,omitempty"`
 	// matching SFTPAction in teleport/api/types/events/events.proto
 	Action int32 `protobuf:"varint,2,opt,name=action,proto3" json:"action,omitempty"`
@@ -3191,10 +3269,16 @@ type SubmitEventRequest struct {
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields
 
-	// anonymized
+	// anonymized, 32 bytes (HMAC-SHA-256) encoded in base64
+	//
+	// PostHog property: tp.cluster_name (still in base64)
 	ClusterName string `protobuf:"bytes,1,opt,name=cluster_name,json=clusterName,proto3" json:"cluster_name,omitempty"`
 	// optional, will default to the ingest time if unset
+	//
+	// PostHog timestamp
 	Timestamp *timestamppb.Timestamp `protobuf:"bytes,2,opt,name=timestamp,proto3" json:"timestamp,omitempty"`
+	// the event being submitted
+	//
 	// Types that are assignable to Event:
 	//
 	//	*SubmitEventRequest_UserLogin
@@ -3895,6 +3979,7 @@ type SubmitEventsRequest struct {
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields
 
+	// individual events to be submitted in a batch, up to 500 at once
 	Events []*SubmitEventRequest `protobuf:"bytes,1,rep,name=events,proto3" json:"events,omitempty"`
 }
 
@@ -4928,7 +5013,7 @@ var file_prehog_v1alpha_teleport_proto_rawDesc = []byte{
 	0x4f, 0x56, 0x45, 0x52, 0x5f, 0x53, 0x54, 0x41, 0x54, 0x55, 0x53, 0x5f, 0x45, 0x52, 0x52, 0x4f,
 	0x52, 0x10, 0x03, 0x12, 0x1b, 0x0a, 0x17, 0x44, 0x49, 0x53, 0x43, 0x4f, 0x56, 0x45, 0x52, 0x5f,
 	0x53, 0x54, 0x41, 0x54, 0x55, 0x53, 0x5f, 0x41, 0x42, 0x4f, 0x52, 0x54, 0x45, 0x44, 0x10, 0x04,
-	0x2a, 0xae, 0x01, 0x0a, 0x03, 0x43, 0x54, 0x41, 0x12, 0x13, 0x0a, 0x0f, 0x43, 0x54, 0x41, 0x5f,
+	0x2a, 0xc7, 0x01, 0x0a, 0x03, 0x43, 0x54, 0x41, 0x12, 0x13, 0x0a, 0x0f, 0x43, 0x54, 0x41, 0x5f,
 	0x55, 0x4e, 0x53, 0x50, 0x45, 0x43, 0x49, 0x46, 0x49, 0x45, 0x44, 0x10, 0x00, 0x12, 0x16, 0x0a,
 	0x12, 0x43, 0x54, 0x41, 0x5f, 0x41, 0x55, 0x54, 0x48, 0x5f, 0x43, 0x4f, 0x4e, 0x4e, 0x45, 0x43,
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@@ -4939,69 +5024,70 @@ var file_prehog_v1alpha_teleport_proto_rawDesc = []byte{
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+	0x70, 0x72, 0x65, 0x68, 0x6f, 0x67, 0x2e, 0x76, 0x31, 0x61, 0x6c, 0x70, 0x68, 0x61, 0x2e, 0x48,
+	0x65, 0x6c, 0x6c, 0x6f, 0x54, 0x65, 0x6c, 0x65, 0x70, 0x6f, 0x72, 0x74, 0x52, 0x65, 0x73, 0x70,
+	0x6f, 0x6e, 0x73, 0x65, 0x22, 0x00, 0x42, 0xc9, 0x01, 0x0a, 0x12, 0x63, 0x6f, 0x6d, 0x2e, 0x70,
+	0x72, 0x65, 0x68, 0x6f, 0x67, 0x2e, 0x76, 0x31, 0x61, 0x6c, 0x70, 0x68, 0x61, 0x42, 0x0d, 0x54,
+	0x65, 0x6c, 0x65, 0x70, 0x6f, 0x72, 0x74, 0x50, 0x72, 0x6f, 0x74, 0x6f, 0x50, 0x01, 0x5a, 0x4b,
+	0x67, 0x69, 0x74, 0x68, 0x75, 0x62, 0x2e, 0x63, 0x6f, 0x6d, 0x2f, 0x67, 0x72, 0x61, 0x76, 0x69,
+	0x74, 0x61, 0x74, 0x69, 0x6f, 0x6e, 0x61, 0x6c, 0x2f, 0x74, 0x65, 0x6c, 0x65, 0x70, 0x6f, 0x72,
+	0x74, 0x2f, 0x67, 0x65, 0x6e, 0x2f, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x2f, 0x67, 0x6f, 0x2f, 0x70,
+	0x72, 0x65, 0x68, 0x6f, 0x67, 0x2f, 0x76, 0x31, 0x61, 0x6c, 0x70, 0x68, 0x61, 0x3b, 0x70, 0x72,
+	0x65, 0x68, 0x6f, 0x67, 0x76, 0x31, 0x61, 0x6c, 0x70, 0x68, 0x61, 0xa2, 0x02, 0x03, 0x50, 0x58,
+	0x58, 0xaa, 0x02, 0x0e, 0x50, 0x72, 0x65, 0x68, 0x6f, 0x67, 0x2e, 0x56, 0x31, 0x61, 0x6c, 0x70,
+	0x68, 0x61, 0xca, 0x02, 0x0e, 0x50, 0x72, 0x65, 0x68, 0x6f, 0x67, 0x5c, 0x56, 0x31, 0x61, 0x6c,
+	0x70, 0x68, 0x61, 0xe2, 0x02, 0x1a, 0x50, 0x72, 0x65, 0x68, 0x6f, 0x67, 0x5c, 0x56, 0x31, 0x61,
+	0x6c, 0x70, 0x68, 0x61, 0x5c, 0x47, 0x50, 0x42, 0x4d, 0x65, 0x74, 0x61, 0x64, 0x61, 0x74, 0x61,
+	0xea, 0x02, 0x0f, 0x50, 0x72, 0x65, 0x68, 0x6f, 0x67, 0x3a, 0x3a, 0x56, 0x31, 0x61, 0x6c, 0x70,
+	0x68, 0x61, 0x62, 0x06, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x33,
 }
 
 var (
diff --git a/gen/proto/js/prehog/v1alpha/teleport_grpc_pb.js b/gen/proto/js/prehog/v1alpha/teleport_grpc_pb.js
index b075793a957..a8bee0db581 100644
--- a/gen/proto/js/prehog/v1alpha/teleport_grpc_pb.js
+++ b/gen/proto/js/prehog/v1alpha/teleport_grpc_pb.js
@@ -89,7 +89,8 @@ function deserialize_prehog_v1alpha_SubmitEventsResponse(buffer_arg) {
 
 
 var TeleportReportingServiceService = exports.TeleportReportingServiceService = {
-  submitEvent: {
+  // equivalent to SubmitEvents with a single event, should be unused by now
+submitEvent: {
     path: '/prehog.v1alpha.TeleportReportingService/SubmitEvent',
     requestStream: false,
     responseStream: false,
@@ -100,7 +101,16 @@ var TeleportReportingServiceService = exports.TeleportReportingServiceService =
     responseSerialize: serialize_prehog_v1alpha_SubmitEventResponse,
     responseDeserialize: deserialize_prehog_v1alpha_SubmitEventResponse,
   },
-  submitEvents: {
+  // encodes and forwards usage events to the PostHog event database; each
+// event is annotated with some properties that depend on the identity of the
+// caller:
+// - tp.account_id (UUID in string form, can be empty if missing from the
+//   license)
+// - tp.license_name (should always be a UUID)
+// - tp.license_authority (name of the authority that signed the license file
+//   used for authentication)
+// - tp.is_cloud (boolean)
+submitEvents: {
     path: '/prehog.v1alpha.TeleportReportingService/SubmitEvents',
     requestStream: false,
     responseStream: false,
diff --git a/gen/proto/js/prehog/v1alpha/teleport_pb.d.ts b/gen/proto/js/prehog/v1alpha/teleport_pb.d.ts
index c90d9c7be80..ea148f47d50 100644
--- a/gen/proto/js/prehog/v1alpha/teleport_pb.d.ts
+++ b/gen/proto/js/prehog/v1alpha/teleport_pb.d.ts
@@ -1922,6 +1922,7 @@ export enum CTA {
     CTA_PREMIUM_SUPPORT = 4,
     CTA_TRUSTED_DEVICES = 5,
     CTA_UPGRADE_BANNER = 6,
+    CTA_BILLING_SUMMARY = 7,
 }
 
 export enum IntegrationEnrollKind {
diff --git a/gen/proto/js/prehog/v1alpha/teleport_pb.js b/gen/proto/js/prehog/v1alpha/teleport_pb.js
index 27dacdf5b5e..dfb3f63a290 100644
--- a/gen/proto/js/prehog/v1alpha/teleport_pb.js
+++ b/gen/proto/js/prehog/v1alpha/teleport_pb.js
@@ -12970,7 +12970,8 @@ proto.prehog.v1alpha.CTA = {
   CTA_ACCESS_REQUESTS: 3,
   CTA_PREMIUM_SUPPORT: 4,
   CTA_TRUSTED_DEVICES: 5,
-  CTA_UPGRADE_BANNER: 6
+  CTA_UPGRADE_BANNER: 6,
+  CTA_BILLING_SUMMARY: 7
 };
 
 /**
diff --git a/proto/prehog/v1alpha/teleport.proto b/proto/prehog/v1alpha/teleport.proto
index 9883c2a56ef..12b47d32a4a 100644
--- a/proto/prehog/v1alpha/teleport.proto
+++ b/proto/prehog/v1alpha/teleport.proto
@@ -19,12 +19,27 @@ package prehog.v1alpha;
 import "google/protobuf/duration.proto";
 import "google/protobuf/timestamp.proto";
 
+// a successful user login
+//
+// PostHog event: tp.user.login
 message UserLoginEvent {
-  // anonymized
+  // anonymized Teleport username, 32 bytes (HMAC-SHA-256) encoded in base64;
+  // should always be a real user as bots and service accounts with long-term
+  // credentials don't ever login
+  //
+  // PostHog property: tp.user_name
   string user_name = 1;
-  // local/github/saml/oidc
+
+  // type of the auth connector used in the login, should be
+  // "local"/"github"/"saml"/"oidc"
+  //
+  // PostHog property: tp.connector_type
   string connector_type = 2;
-  // The anonymized device ID, for logins where device trust is enabled.
+
+  // anonymized device ID, empty or 32 bytes (HMAC-SHA-256) encoded in base64;
+  // for logins where device trust is enabled
+  //
+  // PostHog property: tp.device_id
   string device_id = 3;
 }
 
@@ -44,46 +59,108 @@ message ResourceCreateEvent {
 // the kind of a "resource" as intended by ResourceHeartbeatEvent
 enum ResourceKind {
   RESOURCE_KIND_UNSPECIFIED = 0;
+
+  // PostHog property value: "node"
   RESOURCE_KIND_NODE = 1;
+
+  // PostHog property value: "app_server"
   RESOURCE_KIND_APP_SERVER = 2;
+
+  // PostHog property value: "kube_server"
   RESOURCE_KIND_KUBE_SERVER = 3;
+
+  // PostHog property value: "db_server"
   RESOURCE_KIND_DB_SERVER = 4;
+
+  // PostHog property value: "windows_desktop"
   RESOURCE_KIND_WINDOWS_DESKTOP = 5;
+
+  // ServerV3 ("node") heartbeat with a subkind of "openssh" (as opposed to
+  // empty or "teleport"); not used in keepalives
+  //
+  // PostHog property value: "node.openssh"
   RESOURCE_KIND_NODE_OPENSSH = 6;
 }
 
 // a heartbeat for a resource served by a Teleport instance outside of the
 // control plane (i.e. not auth, not proxy)
+//
+// PostHog event: tp.resource.hb
 message ResourceHeartbeatEvent {
-  // anonymized, 32 bytes (HMAC-SHA-256)
+  // anonymized name of the resource, 32 bytes (HMAC-SHA-256); the name is the
+  // host ID for nodes but the actual user-facing name for other resources, so
+  // an app or a database served by multiple agents won't be counted multiple
+  // times
+  //
+  // PreHog property: tp.resource_name (in base64)
   bytes resource_name = 1;
+
+  // kind of the resource (node, app, db)
+  //
+  // PostHog property: tp.resource_type (as a string, see ResourceKind)
   ResourceKind resource_kind = 2;
+
   // true if the heartbeat has no expiration
+  //
+  // PostHog property: tp.is_static
   bool static = 3;
 }
 
+// an event representing one of several audit events: session.start, port,
+// app.session.start, db.session.start, windows.desktop.session.start; i.e. a
+// SSH shell or port-forward, kubectl exec or kubectl port-forward, DB, App or
+// Desktop connection
+//
+// an earlier encoding (as "tp.session.start") mixed SSH sessions and kubectl
+// execs under a session type of "ssh"
+//
+// PostHog event: tp.session.start
 message SessionStartEvent {
-  // anonymized
+  // anonymized Teleport username, 32 bytes (HMAC-SHA-256) encoded in base64
+  //
+  // PostHog property: tp.user_name
   string user_name = 1;
-  // ssh/kube/desktop, maybe db?
+
+  // type of the session, should be "ssh"/"k8s"/"db"/"app"/"desktop" (matching
+  // the values for api/types.SessionKind) or "app_tcp", "ssh_port_v2" or
+  // "k8s_port" for TCP Application Access connections, SSH port forwards and
+  // kubectl port-forward respectively; a type of "ssh_port" represents either a
+  // SSH port forwarding connection or a kubectl port-forward (not used in new
+  // events)
+  //
+  // PostHog property: tp.session_type
   string session_type = 2;
 }
 
+// the issuance of a user certificate from the user CA
+//
+// PostHog event: tp.certificate.issued
 message UserCertificateIssuedEvent {
-  // The anonymized username/principal of the entity that requested the
-  // certificate.
+  // anonymized Teleport username, 32 bytes (HMAC-SHA-256) encoded in base64; it
+  // can be the username of a bot user rather than of a regular user
+  //
+  // PostHog property: tp.user_name
   string user_name = 1;
-  // The issued certificate TTL.
+
+  // the TTL of the issued certificate, typically 8 or 12 hours
+  //
+  // PostHog property: tp.ttl_minutes (in minutes, rounded up)
   google.protobuf.Duration ttl = 2;
+
   // If true, the certificate was requested by a bot (i.e. Machine ID) user.
+  // PostHog property: tp.is_bot
   bool is_bot = 3;
   // If true, the certificate usage is restricted to database access.
+  // PostHog property: tp.usage_database
   bool usage_database = 4;
   // If true, the certificate usage is restricted to app access.
+  // PostHog property: tp.usage_app
   bool usage_app = 5;
   // If true, the certificate usage is restricted to Kubernetes access.
+  // PostHog property: tp.usage_kubernetes
   bool usage_kubernetes = 6;
   // If true, the certificate usage is restricted to desktop access.
+  // PostHog property: tp.usage_desktop
   bool usage_desktop = 7;
 }
 
@@ -377,15 +454,27 @@ enum CTA {
   CTA_PREMIUM_SUPPORT = 4;
   CTA_TRUSTED_DEVICES = 5;
   CTA_UPGRADE_BANNER = 6;
+  CTA_BILLING_SUMMARY = 7;
 }
 
+// a request forwarded to a kube cluster's API server (other than exec and
+// port-forward)
+//
+// PostHog event: tp.kube.request
 message KubeRequestEvent {
-  // anonymized
+  // anonymized Teleport username, 32 bytes (HMAC-SHA-256) encoded in base64
+  //
+  // PostHog property: tp.user_name
   string user_name = 1;
 }
 
+// an sftp event, represents a single operation on a file
+//
+// PostHog event: tp.sftp
 message SFTPEvent {
-  // anonymized
+  // anonymized Teleport username, 32 bytes (HMAC-SHA-256) encoded in base64
+  //
+  // PostHog property: tp.user_name
   string user_name = 1;
   // matching SFTPAction in teleport/api/types/events/events.proto
   int32 action = 2;
@@ -465,12 +554,17 @@ message UIIntegrationEnrollCompleteEvent {
 }
 
 message SubmitEventRequest {
-  // anonymized
+  // anonymized, 32 bytes (HMAC-SHA-256) encoded in base64
+  //
+  // PostHog property: tp.cluster_name (still in base64)
   string cluster_name = 1;
 
   // optional, will default to the ingest time if unset
+  //
+  // PostHog timestamp
   google.protobuf.Timestamp timestamp = 2;
 
+  // the event being submitted
   oneof event {
     UserLoginEvent user_login = 3;
     SSOCreateEvent sso_create = 4;
@@ -540,6 +634,7 @@ message SubmitEventRequest {
 message SubmitEventResponse {}
 
 message SubmitEventsRequest {
+  // individual events to be submitted in a batch, up to 500 at once
   repeated SubmitEventRequest events = 1;
 }
 message SubmitEventsResponse {}
@@ -548,9 +643,21 @@ message HelloTeleportRequest {}
 message HelloTeleportResponse {}
 
 service TeleportReportingService {
+  // equivalent to SubmitEvents with a single event, should be unused by now
   rpc SubmitEvent(SubmitEventRequest) returns (SubmitEventResponse) {
     option deprecated = true;
   }
+
+  // encodes and forwards usage events to the PostHog event database; each
+  // event is annotated with some properties that depend on the identity of the
+  // caller:
+  // - tp.account_id (UUID in string form, can be empty if missing from the
+  //   license)
+  // - tp.license_name (should always be a UUID)
+  // - tp.license_authority (name of the authority that signed the license file
+  //   used for authentication)
+  // - tp.is_cloud (boolean)
   rpc SubmitEvents(SubmitEventsRequest) returns (SubmitEventsResponse) {}
+
   rpc HelloTeleport(HelloTeleportRequest) returns (HelloTeleportResponse) {}
 }
diff --git a/web/packages/teleport/src/services/userEvent/types.ts b/web/packages/teleport/src/services/userEvent/types.ts
index ab13fe091c4..4b2828be751 100644
--- a/web/packages/teleport/src/services/userEvent/types.ts
+++ b/web/packages/teleport/src/services/userEvent/types.ts
@@ -15,7 +15,6 @@
  */
 
 // these constants are 1:1 with constants found in lib/usagereporter/web/userevent.go
-
 export enum CaptureEvent {
   // UserEvent types
   BannerClickEvent = 'tp.ui.banner.click',
@@ -181,7 +180,6 @@ export type DiscoverEventStepStatus = {
   stepStatusError?: string;
 };
 
-// TODO(mcbattirola): import this from protofile instead of copying it here
 export enum CtaEvent {
   CTA_UNSPECIFIED = 0,
   CTA_AUTH_CONNECTOR = 1,
@@ -190,4 +188,5 @@ export enum CtaEvent {
   CTA_PREMIUM_SUPPORT = 4,
   CTA_TRUSTED_DEVICES = 5,
   CTA_UPGRADE_BANNER = 6,
+  CTA_BILLING_SUMMARY = 7,
 }