diff --git a/gopls/internal/regtest/diagnostics/diagnostics_test.go b/gopls/internal/regtest/diagnostics/diagnostics_test.go
index 433b462349..a2707efdb5 100644
--- a/gopls/internal/regtest/diagnostics/diagnostics_test.go
+++ b/gopls/internal/regtest/diagnostics/diagnostics_test.go
@@ -1650,7 +1650,19 @@ const B = a.B
 	Run(t, mod, func(t *testing.T, env *Env) {
 		env.OpenFile("a/a.go")
 		env.OpenFile("b/b.go")
-		env.Await(env.DiagnosticAtRegexp("a/a.go", `"mod.test/b"`))
+		env.Await(
+			OnceMet(
+				env.DoneWithOpen(),
+				// The Go command sometimes tells us about only one of the import cycle
+				// errors below. For robustness of this test, succeed if we get either.
+				//
+				// TODO(golang/go#52904): we should get *both* of these errors.
+				AnyOf(
+					env.DiagnosticAtRegexpWithMessage("a/a.go", `"mod.test/b"`, "import cycle"),
+					env.DiagnosticAtRegexpWithMessage("b/b.go", `"mod.test/a"`, "import cycle"),
+				),
+			),
+		)
 		env.RegexpReplace("b/b.go", `const B = a\.B`, "")
 		env.SaveBuffer("b/b.go")
 		env.Await(
diff --git a/internal/lsp/regtest/env.go b/internal/lsp/regtest/env.go
index b6b163a87b..f095c38f28 100644
--- a/internal/lsp/regtest/env.go
+++ b/internal/lsp/regtest/env.go
@@ -258,7 +258,7 @@ func checkExpectations(s State, expectations []Expectation) (Verdict, string) {
 		if v > finalVerdict {
 			finalVerdict = v
 		}
-		summary.WriteString(fmt.Sprintf("\t%v: %s\n", v, e.Description()))
+		summary.WriteString(fmt.Sprintf("%v: %s\n", v, e.Description()))
 	}
 	return finalVerdict, summary.String()
 }
diff --git a/internal/lsp/regtest/expectation.go b/internal/lsp/regtest/expectation.go
index 15de33f349..ab808f9e8c 100644
--- a/internal/lsp/regtest/expectation.go
+++ b/internal/lsp/regtest/expectation.go
@@ -96,13 +96,37 @@ func OnceMet(precondition Expectation, mustMeets ...Expectation) *SimpleExpectat
 			return Unmet
 		}
 	}
-	var descriptions []string
-	for _, mustMeet := range mustMeets {
-		descriptions = append(descriptions, mustMeet.Description())
-	}
+	description := describeExpectations(mustMeets...)
 	return &SimpleExpectation{
 		check:       check,
-		description: fmt.Sprintf("once %q is met, must have %q", precondition.Description(), strings.Join(descriptions, "\n")),
+		description: fmt.Sprintf("once %q is met, must have:\n%s", precondition.Description(), description),
+	}
+}
+
+func describeExpectations(expectations ...Expectation) string {
+	var descriptions []string
+	for _, e := range expectations {
+		descriptions = append(descriptions, e.Description())
+	}
+	return strings.Join(descriptions, "\n")
+}
+
+// AnyOf returns an expectation that is satisfied when any of the given
+// expectations is met.
+func AnyOf(anyOf ...Expectation) *SimpleExpectation {
+	check := func(s State) Verdict {
+		for _, e := range anyOf {
+			verdict := e.Check(s)
+			if verdict == Met {
+				return Met
+			}
+		}
+		return Unmet
+	}
+	description := describeExpectations(anyOf...)
+	return &SimpleExpectation{
+		check:       check,
+		description: fmt.Sprintf("Any of:\n%s", description),
 	}
 }