diff --git a/tests/csapi/apidoc_room_alias_test.go b/tests/csapi/apidoc_room_alias_test.go
index 52323369..a86db07a 100644
--- a/tests/csapi/apidoc_room_alias_test.go
+++ b/tests/csapi/apidoc_room_alias_test.go
@@ -1,6 +1,7 @@
 package csapi_tests
 
 import (
+	"net/http"
 	"testing"
 
 	"github.com/tidwall/gjson"
@@ -9,70 +10,460 @@ import (
 	"github.com/matrix-org/complement/internal/client"
 	"github.com/matrix-org/complement/internal/match"
 	"github.com/matrix-org/complement/internal/must"
+	"github.com/matrix-org/complement/runtime"
 )
 
+func setRoomAliasResp(t *testing.T, c *client.CSAPI, roomID, roomAlias string) *http.Response {
+	return c.DoFunc(t, "PUT", []string{"_matrix", "client", "r0", "directory", "room", roomAlias}, client.WithJSONBody(t, map[string]interface{}{
+		"room_id": roomID,
+	}))
+}
+
+func getRoomAliasResp(t *testing.T, c *client.CSAPI, roomAlias string) *http.Response {
+	return c.DoFunc(t, "GET", []string{"_matrix", "client", "r0", "directory", "room", roomAlias})
+}
+
+func deleteRoomAliasResp(t *testing.T, c *client.CSAPI, roomAlias string) *http.Response {
+	return c.DoFunc(t, "DELETE", []string{"_matrix", "client", "r0", "directory", "room", roomAlias})
+}
+
+func listRoomAliasesResp(t *testing.T, c *client.CSAPI, roomID string) *http.Response {
+	return c.DoFunc(t, "GET", []string{"_matrix", "client", "r0", "rooms", roomID, "aliases"})
+}
+
+func setCanonicalAlias(t *testing.T, c *client.CSAPI, roomID string, roomAlias string, altAliases *[]string) *http.Response {
+	content := map[string]interface{}{
+		"alias": roomAlias,
+	}
+	if altAliases != nil {
+		content["alt_aliases"] = altAliases
+	}
+
+	return c.DoFunc(t, "PUT", []string{"_matrix", "client", "r0", "rooms", roomID, "state", "m.room.canonical_alias"}, client.WithJSONBody(t, content))
+}
+
 func TestRoomAlias(t *testing.T) {
-	deployment := Deploy(t, b.BlueprintAlice)
+	deployment := Deploy(t, b.BlueprintOneToOneRoom)
 	defer deployment.Destroy(t)
-	authedClient := deployment.Client(t, "hs1", "@alice:hs1")
+	alice := deployment.Client(t, "hs1", "@alice:hs1")
+	bob := deployment.Client(t, "hs1", "@bob:hs1")
+
 	t.Run("Parallel", func(t *testing.T) {
 		// sytest: PUT /directory/room/:room_alias creates alias
 		t.Run("PUT /directory/room/:room_alias creates alias", func(t *testing.T) {
 			t.Parallel()
-			roomID := authedClient.CreateRoom(t, map[string]interface{}{
-				"visibility": "public",
-				"preset":     "public_chat",
-			})
 
-			roomAlias := "#room_alias_test:hs1"
+			roomID := alice.CreateRoom(t, map[string]interface{}{})
 
-			reqBody := client.WithJSONBody(t, map[string]interface{}{
-				"room_id": roomID,
-			})
+			roomAlias := "#creates_alias:hs1"
 
-			_ = authedClient.MustDoFunc(t, "PUT", []string{"_matrix", "client", "r0", "directory", "room", roomAlias}, reqBody)
+			setRoomAliasResp(t, alice, roomID, roomAlias)
 
-			res := authedClient.MustDoFunc(t, "GET", []string{"_matrix", "client", "r0", "directory", "room", roomAlias})
+			res := getRoomAliasResp(t, alice, roomAlias)
 
 			must.MatchResponse(t, res, match.HTTPResponse{
 				JSON: []match.JSON{
-					match.JSONKeyPresent("room_id"),
-					match.JSONKeyTypeEqual("room_id", gjson.String),
 					match.JSONKeyEqual("room_id", roomID),
 				},
 			})
 		})
+
 		// sytest: GET /rooms/:room_id/aliases lists aliases
 		t.Run("GET /rooms/:room_id/aliases lists aliases", func(t *testing.T) {
 			t.Parallel()
-			roomID := authedClient.CreateRoom(t, map[string]interface{}{
-				"visibility": "public",
-				"preset":     "public_chat",
-			})
+			roomID := alice.CreateRoom(t, map[string]interface{}{})
 
-			res := authedClient.MustDoFunc(t, "GET", []string{"_matrix", "client", "r0", "rooms", roomID, "aliases"})
+			res := listRoomAliasesResp(t, alice, roomID)
 
 			must.MatchResponse(t, res, match.HTTPResponse{
 				JSON: []match.JSON{
-					match.JSONKeyPresent("aliases"),
 					match.JSONKeyEqual("aliases", []interface{}{}),
 				},
 			})
 
-			roomAlias := "#room_alias:hs1"
+			roomAlias := "#lists_aliases:hs1"
+
+			setRoomAliasResp(t, alice, roomID, roomAlias)
+
+			res = listRoomAliasesResp(t, alice, roomID)
 
-			reqBody := client.WithJSONBody(t, map[string]interface{}{
-				"room_id": roomID,
+			must.MatchResponse(t, res, match.HTTPResponse{
+				JSON: []match.JSON{
+					match.JSONKeyEqual("aliases", []interface{}{roomAlias}),
+				},
 			})
+		})
 
-			_ = authedClient.MustDoFunc(t, "PUT", []string{"_matrix", "client", "r0", "directory", "room", roomAlias}, reqBody)
+		// sytest: Only room members can list aliases of a room
+		t.Run("Only room members can list aliases of a room", func(t *testing.T) {
+			t.Parallel()
+			roomID := alice.CreateRoom(t, map[string]interface{}{})
 
-			res = authedClient.MustDoFunc(t, "GET", []string{"_matrix", "client", "r0", "rooms", roomID, "aliases"})
+			roomAlias := "#room_members_list:hs1"
 
+			res := setRoomAliasResp(t, alice, roomID, roomAlias)
 			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 200,
+			})
+
+			// An extra check to make sure we're not being racy rn
+			res = getRoomAliasResp(t, alice, roomAlias)
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 200,
 				JSON: []match.JSON{
-					match.JSONKeyPresent("aliases"),
-					match.JSONKeyEqual("aliases", []interface{}{roomAlias}),
+					match.JSONKeyEqual("room_id", roomID),
+				},
+			})
+
+			res = listRoomAliasesResp(t, bob, roomID)
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 403,
+			})
+		})
+	})
+}
+
+func TestRoomDeleteAlias(t *testing.T) {
+	deployment := Deploy(t, b.BlueprintOneToOneRoom)
+	defer deployment.Destroy(t)
+	alice := deployment.Client(t, "hs1", "@alice:hs1")
+	bob := deployment.Client(t, "hs1", "@bob:hs1")
+
+	t.Run("Parallel", func(t *testing.T) {
+		// sytest: Alias creators can delete alias with no ops
+		t.Run("Alias creators can delete alias with no ops", func(t *testing.T) {
+			t.Parallel()
+			roomID := alice.CreateRoom(t, map[string]interface{}{
+				"preset": "public_chat",
+			})
+
+			bob.JoinRoom(t, roomID, nil)
+			// todo: replace with `SyncUntilJoined`
+			bob.SyncUntilTimelineHas(t, roomID, func(event gjson.Result) bool {
+				return event.Get("type").Str == "m.room.member" &&
+					event.Get("content.membership").Str == "join" &&
+					event.Get("state_key").Str == bob.UserID
+			})
+
+			roomAlias := "#no_ops_delete:hs1"
+
+			res := setRoomAliasResp(t, bob, roomID, roomAlias)
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 200,
+			})
+
+			// An extra check to make sure we're not being racy rn
+			res = getRoomAliasResp(t, bob, roomAlias)
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 200,
+				JSON: []match.JSON{
+					match.JSONKeyEqual("room_id", roomID),
+				},
+			})
+
+			res = deleteRoomAliasResp(t, bob, roomAlias)
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 200,
+			})
+		})
+
+		// sytest: Alias creators can delete canonical alias with no ops
+		t.Run("Alias creators can delete canonical alias with no ops", func(t *testing.T) {
+			t.Parallel()
+			roomID := alice.CreateRoom(t, map[string]interface{}{
+				"preset": "public_chat",
+			})
+
+			bob.JoinRoom(t, roomID, nil)
+			// todo: replace with `SyncUntilJoined`
+			bob.SyncUntilTimelineHas(t, roomID, func(event gjson.Result) bool {
+				return event.Get("type").Str == "m.room.member" &&
+					event.Get("content.membership").Str == "join" &&
+					event.Get("state_key").Str == bob.UserID
+			})
+
+			roomAlias := "#no_ops_delete_canonical:hs1"
+
+			res := setRoomAliasResp(t, bob, roomID, roomAlias)
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 200,
+			})
+
+			// An extra check to make sure we're not being racy rn
+			res = getRoomAliasResp(t, bob, roomAlias)
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 200,
+				JSON: []match.JSON{
+					match.JSONKeyEqual("room_id", roomID),
+				},
+			})
+
+			res = setCanonicalAlias(t, alice, roomID, roomAlias, nil)
+
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 200,
+				JSON: []match.JSON{
+					match.JSONKeyPresent("event_id"),
+				},
+			})
+
+			res = deleteRoomAliasResp(t, bob, roomAlias)
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 200,
+			})
+		})
+
+		// sytest: Deleting a non-existent alias should return a 404
+		t.Run("Deleting a non-existent alias should return a 404", func(t *testing.T) {
+			t.Parallel()
+
+			roomAlias := "#scatman_portal:hs1"
+
+			res := deleteRoomAliasResp(t, bob, roomAlias)
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 404,
+				JSON: []match.JSON{
+					match.JSONKeyEqual("errcode", "M_NOT_FOUND"),
+				},
+			})
+		})
+	})
+}
+
+func TestRoomCanonicalAlias(t *testing.T) {
+	deployment := Deploy(t, b.BlueprintAlice)
+	defer deployment.Destroy(t)
+	alice := deployment.Client(t, "hs1", "@alice:hs1")
+
+	t.Run("Parallel", func(t *testing.T) {
+
+		// The original sytest has been split out into three tests, the test name only pertained to the first.
+		// sytest: Canonical alias can be set
+		t.Run("m.room.canonical_alias accepts present aliases", func(t *testing.T) {
+
+			roomID := alice.CreateRoom(t, map[string]interface{}{})
+
+			t.Parallel()
+
+			roomAlias := "#accepts_present_aliases:hs1"
+
+			res := setRoomAliasResp(t, alice, roomID, roomAlias)
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 200,
+			})
+
+			res = setCanonicalAlias(t, alice, roomID, roomAlias, nil)
+
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 200,
+				JSON: []match.JSON{
+					match.JSONKeyPresent("event_id"),
+				},
+			})
+		})
+
+		// part of "Canonical alias can be set"
+		t.Run("m.room.canonical_alias rejects missing aliases", func(t *testing.T) {
+			runtime.SkipIf(t, runtime.Dendrite) // FIXME https://github.com/matrix-org/dendrite/issues/2068
+
+			roomID := alice.CreateRoom(t, map[string]interface{}{})
+
+			t.Parallel()
+
+			roomAlias := "#rejects_missing:hs1"
+
+			res := setCanonicalAlias(t, alice, roomID, roomAlias, nil)
+
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 400,
+				JSON: []match.JSON{
+					match.JSONKeyEqual("errcode", "M_BAD_ALIAS"),
+				},
+			})
+		})
+
+		// part of "Canonical alias can be set"
+		t.Run("m.room.canonical_alias rejects invalid aliases", func(t *testing.T) {
+			runtime.SkipIf(t, runtime.Dendrite) // FIXME https://github.com/matrix-org/dendrite/issues/2069
+
+			roomID := alice.CreateRoom(t, map[string]interface{}{})
+
+			t.Parallel()
+
+			roomAlias := "%invalid_aliases:hs1"
+
+			res := setCanonicalAlias(t, alice, roomID, roomAlias, nil)
+
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 400,
+				JSON: []match.JSON{
+					match.JSONKeyEqual("errcode", "M_INVALID_PARAM"),
+				},
+			})
+		})
+
+		t.Run("m.room.canonical_alias setting rejects deleted aliases", func(t *testing.T) {
+			runtime.SkipIf(t, runtime.Dendrite) // FIXME https://github.com/matrix-org/dendrite/issues/2068
+
+			roomID := alice.CreateRoom(t, map[string]interface{}{})
+
+			t.Parallel()
+
+			roomAlias := "#deleted_aliases:hs1"
+
+			res := setRoomAliasResp(t, alice, roomID, roomAlias)
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 200,
+			})
+
+			res = deleteRoomAliasResp(t, alice, roomAlias)
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 200,
+			})
+
+			// An extra check to make sure we're not being racy rn
+			res = getRoomAliasResp(t, alice, roomAlias)
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 404,
+			})
+
+			res = setCanonicalAlias(t, alice, roomID, roomAlias, nil)
+
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 400,
+				JSON: []match.JSON{
+					match.JSONKeyEqual("errcode", "M_BAD_ALIAS"),
+				},
+			})
+		})
+
+		t.Run("m.room.canonical_alias rejects alias pointing to different local room", func(t *testing.T) {
+			runtime.SkipIf(t, runtime.Dendrite) // FIXME https://github.com/matrix-org/dendrite/issues/2068
+
+			room1 := alice.CreateRoom(t, map[string]interface{}{})
+			room2 := alice.CreateRoom(t, map[string]interface{}{})
+
+			t.Parallel()
+
+			roomAlias := "#diffroom1:hs1"
+
+			res := setRoomAliasResp(t, alice, room1, roomAlias)
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 200,
+			})
+
+			res = setCanonicalAlias(t, alice, room2, roomAlias, nil)
+
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 400,
+				JSON: []match.JSON{
+					match.JSONKeyEqual("errcode", "M_BAD_ALIAS"),
+				},
+			})
+		})
+
+		// The original sytest has been split out into three tests, the test name only pertained to the first.
+		// sytest: Canonical alias can include alt_aliases
+		t.Run("m.room.canonical_alias accepts present alt_aliases", func(t *testing.T) {
+			roomID := alice.CreateRoom(t, map[string]interface{}{})
+
+			t.Parallel()
+
+			roomAlias := "#alt_present_alias:hs1"
+
+			res := setRoomAliasResp(t, alice, roomID, roomAlias)
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 200,
+			})
+
+			res = setCanonicalAlias(t, alice, roomID, roomAlias, &[]string{roomAlias})
+
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 200,
+				JSON: []match.JSON{
+					match.JSONKeyPresent("event_id"),
+				},
+			})
+		})
+
+		// part of "Canonical alias can include alt_aliases"
+		t.Run("m.room.canonical_alias rejects missing aliases", func(t *testing.T) {
+			runtime.SkipIf(t, runtime.Dendrite) // FIXME https://github.com/matrix-org/dendrite/issues/2068
+			roomID := alice.CreateRoom(t, map[string]interface{}{})
+
+			t.Parallel()
+
+			roomAlias := "#alt_missing:hs1"
+			wrongRoomAlias := "#alt_missing_wrong:hs1"
+
+			res := setRoomAliasResp(t, alice, roomID, roomAlias)
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 200,
+			})
+
+			res = setCanonicalAlias(t, alice, roomID, roomAlias, &[]string{wrongRoomAlias})
+
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 400,
+				JSON: []match.JSON{
+					match.JSONKeyEqual("errcode", "M_BAD_ALIAS"),
+				},
+			})
+		})
+
+		// part of "Canonical alias can include alt_aliases"
+		t.Run("m.room.canonical_alias rejects invalid aliases", func(t *testing.T) {
+			runtime.SkipIf(t, runtime.Dendrite) // FIXME https://github.com/matrix-org/dendrite/issues/2069
+			roomID := alice.CreateRoom(t, map[string]interface{}{})
+
+			t.Parallel()
+
+			roomAlias := "#alt_invalid:hs1"
+			wrongRoomAlias := "%alt_invalid_wrong:hs1"
+
+			res := setRoomAliasResp(t, alice, roomID, roomAlias)
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 200,
+			})
+
+			res = setCanonicalAlias(t, alice, roomID, roomAlias, &[]string{wrongRoomAlias})
+
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 400,
+				JSON: []match.JSON{
+					match.JSONKeyEqual("errcode", "M_INVALID_PARAM"),
+				},
+			})
+		})
+
+		// part of "Canonical alias can include alt_aliases"
+		t.Run("m.room.canonical_alias rejects alt_alias pointing to different local room", func(t *testing.T) {
+			runtime.SkipIf(t, runtime.Dendrite) // FIXME https://github.com/matrix-org/dendrite/issues/2068
+
+			room1 := alice.CreateRoom(t, map[string]interface{}{})
+			room2 := alice.CreateRoom(t, map[string]interface{}{})
+
+			t.Parallel()
+
+			room1Alias := "#alt_room1:hs1"
+			room2Alias := "#alt_room2:hs1"
+
+			res := setRoomAliasResp(t, alice, room1, room1Alias)
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 200,
+			})
+
+			res = setRoomAliasResp(t, alice, room2, room2Alias)
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 200,
+			})
+
+			res = setCanonicalAlias(t, alice, room2, room2Alias, &[]string{room1Alias})
+
+			must.MatchResponse(t, res, match.HTTPResponse{
+				StatusCode: 400,
+				JSON: []match.JSON{
+					match.JSONKeyEqual("errcode", "M_BAD_ALIAS"),
 				},
 			})
 		})