diff --git a/pkg/sql/opt/invertedidx/trigram_test.go b/pkg/sql/opt/invertedidx/trigram_test.go
new file mode 100644
index 000000000000..95d9504aee2f
--- /dev/null
+++ b/pkg/sql/opt/invertedidx/trigram_test.go
@@ -0,0 +1,129 @@
+// Copyright 2022 The Cockroach Authors.
+//
+// Use of this software is governed by the Business Source License
+// included in the file licenses/BSL.txt.
+//
+// As of the Change Date specified in that file, in accordance with
+// the Business Source License, use of this software will be governed
+// by the Apache License, Version 2.0, included in the file
+// licenses/APL.txt.
+
+package invertedidx_test
+
+import (
+	"testing"
+
+	"github.com/cockroachdb/cockroach/pkg/settings/cluster"
+	"github.com/cockroachdb/cockroach/pkg/sql/opt/invertedidx"
+	"github.com/cockroachdb/cockroach/pkg/sql/opt/norm"
+	"github.com/cockroachdb/cockroach/pkg/sql/opt/testutils"
+	"github.com/cockroachdb/cockroach/pkg/sql/opt/testutils/testcat"
+	"github.com/cockroachdb/cockroach/pkg/sql/sem/eval"
+	"github.com/cockroachdb/cockroach/pkg/sql/sem/tree"
+	"github.com/stretchr/testify/require"
+)
+
+func TestTryFilterTrigram(t *testing.T) {
+	semaCtx := tree.MakeSemaContext()
+	st := cluster.MakeTestingClusterSettings()
+	evalCtx := eval.NewTestingEvalContext(st)
+
+	tc := testcat.New()
+	if _, err := tc.ExecuteDDL(
+		"CREATE TABLE t (s STRING, INVERTED INDEX (s gin_trgm_ops))",
+	); err != nil {
+		t.Fatal(err)
+	}
+	var f norm.Factory
+	f.Init(evalCtx, tc)
+	md := f.Metadata()
+	tn := tree.NewUnqualifiedTableName("t")
+	tab := md.AddTable(tc.Table(tn), tn)
+	trigramOrd := 1
+
+	// If we can create an inverted filter with the given filter expression and
+	// index, ok=true. If the spans in the resulting inverted index constraint
+	// do not have duplicate primary keys, unique=true. If the spans are tight,
+	// tight=true and remainingFilters="". Otherwise, tight is false and
+	// remainingFilters contains some or all of the original filters.
+	testCases := []struct {
+		filters string
+		ok      bool
+		unique  bool
+	}{
+		// Test LIKE with percents on both sides
+		// TODO(jordan): we could make expressions with just a single trigram
+		// tight, because we would know for sure that we wouldn't need to recheck
+		// the condition once the row is returned. But, it's probably not that
+		// important of an optimization.
+		{filters: "s LIKE '%foo%'", ok: true, unique: true},
+		{filters: "s LIKE '%blorp%'", ok: true, unique: false},
+		{filters: "s LIKE 'foo%'", ok: true, unique: true},
+		{filters: "s LIKE 'blorp%'", ok: true, unique: false},
+		{filters: "s ILIKE '%foo%'", ok: true, unique: true},
+		{filters: "s ILIKE '%blorp%'", ok: true, unique: false},
+		// Queries that are too short to have any trigrams do not produce filters.
+		{filters: "s LIKE '%fo%'", ok: false},
+		{filters: "s ILIKE '%fo%'", ok: false},
+		{filters: "s LIKE '%fo%ab%ru%'", ok: false},
+
+		// AND and OR for two LIKE queries behave as expected.
+		{filters: "s LIKE '%lkj%' AND s LIKE '%bla%'", ok: true, unique: true},
+		{filters: "s LIKE '%lkj%' OR s LIKE '%bla%'", ok: true, unique: false},
+
+		// Similarity queries.
+		{filters: "s % 'lkjsdlkj'", ok: true, unique: false},
+		{filters: "s % 'lkj'", ok: true, unique: true},
+		// Can't generate trigrams from such a short constant.
+		{filters: "s % 'lj'", ok: false},
+
+		// AND and OR for two similarity queries behave as expected.
+		{filters: "s % 'lkj' AND s % 'bla'", ok: true, unique: true},
+		{filters: "s % 'lkj' OR s % 'bla'", ok: true, unique: false},
+
+		// Can combine similarity and LIKE queries and still get inverted
+		// expressions.
+		{filters: "s % 'lkj' AND s LIKE 'blort'", ok: true, unique: false},
+		{filters: "s % 'lkj' OR s LIKE 'blort'", ok: true, unique: false},
+
+		// Equality queries.
+		{filters: "s = 'lkjsdlkj'", ok: true, unique: false},
+		{filters: "s = 'lkj'", ok: true, unique: true},
+		{filters: "s = 'lkj' OR s LIKE 'blah'", ok: true, unique: false},
+	}
+
+	for _, tc := range testCases {
+		t.Logf("test case: %v", tc)
+		filters := testutils.BuildFilters(t, &f, &semaCtx, evalCtx, tc.filters)
+
+		// We're not testing that the correct SpanExpression is returned here;
+		// that is tested elsewhere. This is just testing that we are constraining
+		// the index when we expect to and we have the correct values for tight,
+		// unique, and remainingFilters.
+		spanExpr, _, remainingFilters, _, ok := invertedidx.TryFilterInvertedIndex(
+			evalCtx,
+			&f,
+			filters,
+			nil, /* optionalFilters */
+			tab,
+			md.Table(tab).Index(trigramOrd),
+			nil, /* computedColumns */
+		)
+		if tc.ok != ok {
+			t.Fatalf("expected %v, got %v", tc.ok, ok)
+		}
+		if !ok {
+			continue
+		}
+
+		if spanExpr.Tight {
+			t.Fatalf("We never expected our inverted expression to be tight")
+		}
+		if tc.unique != spanExpr.Unique {
+			t.Fatalf("For (%s), expected unique=%v, but got %v", tc.filters, tc.unique, spanExpr.Unique)
+		}
+
+		require.Equal(t, filters.String(), remainingFilters.String(),
+			"mismatched remaining filters")
+	}
+}