diff --git a/coderd/idpsync/organization.go b/coderd/idpsync/organization.go
index 12d79bc047776..8b430fe84a3e6 100644
--- a/coderd/idpsync/organization.go
+++ b/coderd/idpsync/organization.go
@@ -45,6 +45,8 @@ func (s AGPLIDPSync) UpdateOrganizationSettings(ctx context.Context, db database
 }
 
 func (s AGPLIDPSync) OrganizationSyncSettings(ctx context.Context, db database.Store) (*OrganizationSyncSettings, error) {
+	// If this logic is ever updated, make sure to update the corresponding
+	// checkIDPOrgSync in coderd/telemetry/telemetry.go.
 	rlv := s.Manager.Resolver(db)
 	orgSettings, err := s.SyncSettings.Organization.Resolve(ctx, rlv)
 	if err != nil {
diff --git a/coderd/telemetry/telemetry.go b/coderd/telemetry/telemetry.go
index 233450c43d943..497a1109c7db9 100644
--- a/coderd/telemetry/telemetry.go
+++ b/coderd/telemetry/telemetry.go
@@ -4,6 +4,7 @@ import (
 	"bytes"
 	"context"
 	"crypto/sha256"
+	"database/sql"
 	"encoding/json"
 	"errors"
 	"fmt"
@@ -244,6 +245,11 @@ func (r *remoteReporter) deployment() error {
 		return xerrors.Errorf("install source must be <=64 chars: %s", installSource)
 	}
 
+	idpOrgSync, err := checkIDPOrgSync(r.ctx, r.options.Database, r.options.DeploymentConfig)
+	if err != nil {
+		r.options.Logger.Debug(r.ctx, "check IDP org sync", slog.Error(err))
+	}
+
 	data, err := json.Marshal(&Deployment{
 		ID:              r.options.DeploymentID,
 		Architecture:    sysInfo.Architecture,
@@ -263,6 +269,7 @@ func (r *remoteReporter) deployment() error {
 		MachineID:       sysInfo.UniqueID,
 		StartedAt:       r.startedAt,
 		ShutdownAt:      r.shutdownAt,
+		IDPOrgSync:      &idpOrgSync,
 	})
 	if err != nil {
 		return xerrors.Errorf("marshal deployment: %w", err)
@@ -284,6 +291,45 @@ func (r *remoteReporter) deployment() error {
 	return nil
 }
 
+// idpOrgSyncConfig is a subset of
+// https://github.com/coder/coder/blob/5c6578d84e2940b9cfd04798c45e7c8042c3fe0e/coderd/idpsync/organization.go#L148
+type idpOrgSyncConfig struct {
+	Field string `json:"field"`
+}
+
+// checkIDPOrgSync inspects the server flags and the runtime config. It's based on
+// the OrganizationSyncEnabled function from enterprise/coderd/enidpsync/organizations.go.
+// It has one distinct difference: it doesn't check if the license entitles to the
+// feature, it only checks if the feature is configured.
+//
+// The above function is not used because it's very hard to make it available in
+// the telemetry package due to coder/coder package structure and initialization
+// order of the coder server.
+//
+// We don't check license entitlements because it's also hard to do from the
+// telemetry package, and the config check should be sufficient for telemetry purposes.
+//
+// While this approach duplicates code, it's simpler than the alternative.
+//
+// See https://github.com/coder/coder/pull/16323 for more details.
+func checkIDPOrgSync(ctx context.Context, db database.Store, values *codersdk.DeploymentValues) (bool, error) {
+	// key based on https://github.com/coder/coder/blob/5c6578d84e2940b9cfd04798c45e7c8042c3fe0e/coderd/idpsync/idpsync.go#L168
+	syncConfigRaw, err := db.GetRuntimeConfig(ctx, "organization-sync-settings")
+	if err != nil {
+		if errors.Is(err, sql.ErrNoRows) {
+			// If the runtime config is not set, we check if the deployment config
+			// has the organization field set.
+			return values != nil && values.OIDC.OrganizationField != "", nil
+		}
+		return false, xerrors.Errorf("get runtime config: %w", err)
+	}
+	syncConfig := idpOrgSyncConfig{}
+	if err := json.Unmarshal([]byte(syncConfigRaw), &syncConfig); err != nil {
+		return false, xerrors.Errorf("unmarshal runtime config: %w", err)
+	}
+	return syncConfig.Field != "", nil
+}
+
 // createSnapshot collects a full snapshot from the database.
 func (r *remoteReporter) createSnapshot() (*Snapshot, error) {
 	var (
@@ -518,6 +564,21 @@ func (r *remoteReporter) createSnapshot() (*Snapshot, error) {
 		}
 		return nil
 	})
+	eg.Go(func() error {
+		// Warning: When an organization is deleted, it's completely removed from
+		// the database. It will no longer be reported, and there will be no other
+		// indicator that it was deleted. This requires special handling when
+		// interpreting the telemetry data later.
+		orgs, err := r.options.Database.GetOrganizations(r.ctx, database.GetOrganizationsParams{})
+		if err != nil {
+			return xerrors.Errorf("get organizations: %w", err)
+		}
+		snapshot.Organizations = make([]Organization, 0, len(orgs))
+		for _, org := range orgs {
+			snapshot.Organizations = append(snapshot.Organizations, ConvertOrganization(org))
+		}
+		return nil
+	})
 
 	err := eg.Wait()
 	if err != nil {
@@ -916,6 +977,14 @@ func ConvertExternalProvisioner(id uuid.UUID, tags map[string]string, provisione
 	}
 }
 
+func ConvertOrganization(org database.Organization) Organization {
+	return Organization{
+		ID:        org.ID,
+		CreatedAt: org.CreatedAt,
+		IsDefault: org.IsDefault,
+	}
+}
+
 // Snapshot represents a point-in-time anonymized database dump.
 // Data is aggregated by latest on the server-side, so partial data
 // can be sent without issue.
@@ -942,6 +1011,7 @@ type Snapshot struct {
 	WorkspaceModules          []WorkspaceModule           `json:"workspace_modules"`
 	Workspaces                []Workspace                 `json:"workspaces"`
 	NetworkEvents             []NetworkEvent              `json:"network_events"`
+	Organizations             []Organization              `json:"organizations"`
 }
 
 // Deployment contains information about the host running Coder.
@@ -964,6 +1034,9 @@ type Deployment struct {
 	MachineID       string                     `json:"machine_id"`
 	StartedAt       time.Time                  `json:"started_at"`
 	ShutdownAt      *time.Time                 `json:"shutdown_at"`
+	// While IDPOrgSync will always be set, it's nullable to make
+	// the struct backwards compatible with older coder versions.
+	IDPOrgSync *bool `json:"idp_org_sync"`
 }
 
 type APIKey struct {
@@ -1457,6 +1530,12 @@ func NetworkEventFromProto(proto *tailnetproto.TelemetryEvent) (NetworkEvent, er
 	}, nil
 }
 
+type Organization struct {
+	ID        uuid.UUID `json:"id"`
+	IsDefault bool      `json:"is_default"`
+	CreatedAt time.Time `json:"created_at"`
+}
+
 type noopReporter struct{}
 
 func (*noopReporter) Report(_ *Snapshot) {}
diff --git a/coderd/telemetry/telemetry_test.go b/coderd/telemetry/telemetry_test.go
index e0cbfd1cfa193..b892e28e89d58 100644
--- a/coderd/telemetry/telemetry_test.go
+++ b/coderd/telemetry/telemetry_test.go
@@ -22,7 +22,10 @@ import (
 	"github.com/coder/coder/v2/coderd/database/dbmem"
 	"github.com/coder/coder/v2/coderd/database/dbtestutil"
 	"github.com/coder/coder/v2/coderd/database/dbtime"
+	"github.com/coder/coder/v2/coderd/idpsync"
+	"github.com/coder/coder/v2/coderd/runtimeconfig"
 	"github.com/coder/coder/v2/coderd/telemetry"
+	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/testutil"
 )
 
@@ -40,22 +43,33 @@ func TestTelemetry(t *testing.T) {
 		db := dbmem.New()
 
 		ctx := testutil.Context(t, testutil.WaitMedium)
+
+		org, err := db.GetDefaultOrganization(ctx)
+		require.NoError(t, err)
+
 		_, _ = dbgen.APIKey(t, db, database.APIKey{})
 		_ = dbgen.ProvisionerJob(t, db, nil, database.ProvisionerJob{
-			Provisioner:   database.ProvisionerTypeTerraform,
-			StorageMethod: database.ProvisionerStorageMethodFile,
-			Type:          database.ProvisionerJobTypeTemplateVersionDryRun,
+			Provisioner:    database.ProvisionerTypeTerraform,
+			StorageMethod:  database.ProvisionerStorageMethodFile,
+			Type:           database.ProvisionerJobTypeTemplateVersionDryRun,
+			OrganizationID: org.ID,
 		})
 		_ = dbgen.Template(t, db, database.Template{
-			Provisioner: database.ProvisionerTypeTerraform,
+			Provisioner:    database.ProvisionerTypeTerraform,
+			OrganizationID: org.ID,
 		})
 		sourceExampleID := uuid.NewString()
 		_ = dbgen.TemplateVersion(t, db, database.TemplateVersion{
 			SourceExampleID: sql.NullString{String: sourceExampleID, Valid: true},
+			OrganizationID:  org.ID,
+		})
+		_ = dbgen.TemplateVersion(t, db, database.TemplateVersion{
+			OrganizationID: org.ID,
 		})
-		_ = dbgen.TemplateVersion(t, db, database.TemplateVersion{})
 		user := dbgen.User(t, db, database.User{})
-		_ = dbgen.Workspace(t, db, database.WorkspaceTable{})
+		_ = dbgen.Workspace(t, db, database.WorkspaceTable{
+			OrganizationID: org.ID,
+		})
 		_ = dbgen.WorkspaceApp(t, db, database.WorkspaceApp{
 			SharingLevel: database.AppSharingLevelOwner,
 			Health:       database.WorkspaceAppHealthDisabled,
@@ -112,6 +126,7 @@ func TestTelemetry(t *testing.T) {
 		require.Len(t, snapshot.WorkspaceAgentStats, 1)
 		require.Len(t, snapshot.WorkspaceProxies, 1)
 		require.Len(t, snapshot.WorkspaceModules, 1)
+		require.Len(t, snapshot.Organizations, 1)
 
 		wsa := snapshot.WorkspaceAgents[0]
 		require.Len(t, wsa.Subsystems, 2)
@@ -128,6 +143,19 @@ func TestTelemetry(t *testing.T) {
 		})
 		require.Equal(t, tvs[0].SourceExampleID, &sourceExampleID)
 		require.Nil(t, tvs[1].SourceExampleID)
+
+		for _, entity := range snapshot.Workspaces {
+			require.Equal(t, entity.OrganizationID, org.ID)
+		}
+		for _, entity := range snapshot.ProvisionerJobs {
+			require.Equal(t, entity.OrganizationID, org.ID)
+		}
+		for _, entity := range snapshot.TemplateVersions {
+			require.Equal(t, entity.OrganizationID, org.ID)
+		}
+		for _, entity := range snapshot.Templates {
+			require.Equal(t, entity.OrganizationID, org.ID)
+		}
 	})
 	t.Run("HashedEmail", func(t *testing.T) {
 		t.Parallel()
@@ -243,6 +271,41 @@ func TestTelemetry(t *testing.T) {
 			require.Equal(t, c.want, telemetry.GetModuleSourceType(c.source))
 		}
 	})
+	t.Run("IDPOrgSync", func(t *testing.T) {
+		t.Parallel()
+		ctx := testutil.Context(t, testutil.WaitMedium)
+		db, _ := dbtestutil.NewDB(t)
+
+		// 1. No org sync settings
+		deployment, _ := collectSnapshot(t, db, nil)
+		require.False(t, *deployment.IDPOrgSync)
+
+		// 2. Org sync settings set in server flags
+		deployment, _ = collectSnapshot(t, db, func(opts telemetry.Options) telemetry.Options {
+			opts.DeploymentConfig = &codersdk.DeploymentValues{
+				OIDC: codersdk.OIDCConfig{
+					OrganizationField: "organizations",
+				},
+			}
+			return opts
+		})
+		require.True(t, *deployment.IDPOrgSync)
+
+		// 3. Org sync settings set in runtime config
+		org, err := db.GetDefaultOrganization(ctx)
+		require.NoError(t, err)
+		sync := idpsync.NewAGPLSync(testutil.Logger(t), runtimeconfig.NewManager(), idpsync.DeploymentSyncSettings{})
+		err = sync.UpdateOrganizationSettings(ctx, db, idpsync.OrganizationSyncSettings{
+			Field: "organizations",
+			Mapping: map[string][]uuid.UUID{
+				"first": {org.ID},
+			},
+			AssignDefault: true,
+		})
+		require.NoError(t, err)
+		deployment, _ = collectSnapshot(t, db, nil)
+		require.True(t, *deployment.IDPOrgSync)
+	})
 }
 
 // nolint:paralleltest
diff --git a/enterprise/coderd/enidpsync/organizations.go b/enterprise/coderd/enidpsync/organizations.go
index 313d90fac8a9f..826144afc1492 100644
--- a/enterprise/coderd/enidpsync/organizations.go
+++ b/enterprise/coderd/enidpsync/organizations.go
@@ -19,6 +19,8 @@ func (e EnterpriseIDPSync) OrganizationSyncEnabled(ctx context.Context, db datab
 		return false
 	}
 
+	// If this logic is ever updated, make sure to update the corresponding
+	// checkIDPOrgSync in coderd/telemetry/telemetry.go.
 	settings, err := e.OrganizationSyncSettings(ctx, db)
 	if err == nil && settings.Field != "" {
 		return true