diff --git a/pkg/cli/statement_bundle.go b/pkg/cli/statement_bundle.go
index 28d9ad909b60..19a2835a56f4 100644
--- a/pkg/cli/statement_bundle.go
+++ b/pkg/cli/statement_bundle.go
@@ -149,6 +149,7 @@ func runBundleRecreate(cmd *cobra.Command, args []string) (resErr error) {
 
 		if placeholderPairs != nil {
 			placeholderToColMap := make(map[int]string)
+			placeholderFQColNames := make(map[string]struct{})
 			for _, placeholderPairStr := range placeholderPairs {
 				pair := strings.Split(placeholderPairStr, "=")
 				if len(pair) != 2 {
@@ -159,8 +160,11 @@ func runBundleRecreate(cmd *cobra.Command, args []string) (resErr error) {
 					return err
 				}
 				placeholderToColMap[n] = pair[1]
+				placeholderFQColNames[pair[1]] = struct{}{}
 			}
-			inputs, outputs, err := getExplainCombinations(conn, explainPrefix, placeholderToColMap, bundle)
+			inputs, outputs, err := getExplainCombinations(
+				conn, explainPrefix, placeholderToColMap, placeholderFQColNames, bundle,
+			)
 			if err != nil {
 				return err
 			}
@@ -209,6 +213,7 @@ func getExplainCombinations(
 	conn clisqlclient.Conn,
 	explainPrefix string,
 	placeholderToColMap map[int]string,
+	placeholderFQColNames map[string]struct{},
 	bundle *statementBundle,
 ) (inputs [][]string, explainOutputs []string, err error) {
 
@@ -273,6 +278,11 @@ func getExplainCombinations(
 			}
 			col := columns[0]
 			fqColName := fmt.Sprintf("%s.%s", tableName, col)
+			if _, isPlaceholder := placeholderFQColNames[fqColName]; !isPlaceholder {
+				// This column is not one of the placeholder values, so simply
+				// ignore it.
+				continue
+			}
 			d, _, err := tree.ParseDTimestamp(nil, stat["created_at"].(string), time.Microsecond)
 			if err != nil {
 				panic(err)
@@ -285,7 +295,9 @@ func getExplainCombinations(
 
 			typ := stat["histo_col_type"].(string)
 			if typ == "" {
-				fmt.Println("Ignoring column with empty type ", col)
+				// Empty 'histo_col_type' is used when there is no histogram for
+				// the column, simply skip this stat (see stats/json.go for more
+				// details).
 				continue
 			}
 			colTypeRef, err := parser.GetTypeFromValidSQLSyntax(typ)
@@ -300,6 +312,10 @@ func getExplainCombinations(
 				continue
 			}
 			buckets := stat["histo_buckets"].([]interface{})
+			// addedNonExistent tracks whether we included at least one
+			// "previous" datum which - according to the histograms - is not
+			// present in the table.
+			var addedNonExistent bool
 			var maxUpperBound tree.Datum
 			for _, b := range buckets {
 				bucket := b.(map[string]interface{})
@@ -318,9 +334,24 @@ func getExplainCombinations(
 				if maxUpperBound == nil || maxUpperBound.Compare(&evalCtx, datum) < 0 {
 					maxUpperBound = datum
 				}
-				if numRange > 0 {
-					if prev, ok := datum.Prev(&evalCtx); ok {
+				// If we have any datums within the bucket (i.e. not equal to
+				// the upper bound), we always attempt to add a "previous" to
+				// the upper bound datum.
+				addPrevious := numRange > 0
+				if numRange == 0 && !addedNonExistent {
+					// If our bucket says that there are no values present in
+					// the table between the current upper bound and the upper
+					// bound of the previous histogram bucket, then we only
+					// attempt to add the "previous" non-existent datum if we
+					// haven't done so already (this is to avoid the redundant
+					// non-existent values which would get treated in the same
+					// fashion anyway).
+					addPrevious = true
+				}
+				if addPrevious {
+					if prev, ok := tree.DatumPrev(datum, &evalCtx, &evalCtx.CollationEnv); ok {
 						bucketMap[key] = append(bucketMap[key], tree.AsStringWithFlags(prev, fmtCtx))
+						addedNonExistent = addedNonExistent || numRange == 0
 					}
 				}
 			}
@@ -330,7 +361,7 @@ func getExplainCombinations(
 			}
 			// Create a value that's outside of histogram range by incrementing the
 			// max value that we've seen.
-			if outside, ok := maxUpperBound.Next(&evalCtx); ok {
+			if outside, ok := tree.DatumNext(maxUpperBound, &evalCtx, &evalCtx.CollationEnv); ok {
 				colSamples = append(colSamples, tree.AsStringWithFlags(outside, fmtCtx))
 			}
 			sort.Strings(colSamples)
@@ -386,7 +417,8 @@ func getExplainCombinations(
 func getExplainOutputs(
 	conn clisqlclient.Conn, explainPrefix string, statement string, inputs [][]string,
 ) (explainStrings []string, err error) {
-	for _, values := range inputs {
+	fmt.Printf("trying %d placeholder combinations\n", len(inputs))
+	for i, values := range inputs {
 		// Run an explain for each possible input.
 		query := fmt.Sprintf("%s %s", explainPrefix, statement)
 		args := make([]interface{}, len(values))
@@ -409,6 +441,9 @@ func getExplainOutputs(
 			return nil, err
 		}
 		explainStrings = append(explainStrings, explainStr.String())
+		if (i+1)%1000 == 0 {
+			fmt.Printf("%d placeholder combinations are done\n", i+1)
+		}
 	}
 	return explainStrings, nil
 }
diff --git a/pkg/cli/statement_bundle_test.go b/pkg/cli/statement_bundle_test.go
index 5dbcf51daffb..01bd17fd75cf 100644
--- a/pkg/cli/statement_bundle_test.go
+++ b/pkg/cli/statement_bundle_test.go
@@ -32,10 +32,11 @@ import (
 func TestRunExplainCombinations(t *testing.T) {
 	defer leaktest.AfterTest(t)()
 	tests := []struct {
-		bundlePath          string
-		placeholderToColMap map[int]string
-		expectedInputs      [][]string
-		expectedOutputs     []string
+		bundlePath            string
+		placeholderToColMap   map[int]string
+		placeholderFQColNames map[string]struct{}
+		expectedInputs        [][]string
+		expectedOutputs       []string
 	}{
 		{
 			bundlePath: "bundle",
@@ -43,6 +44,10 @@ func TestRunExplainCombinations(t *testing.T) {
 				1: "public.a.a",
 				2: "public.a.b",
 			},
+			placeholderFQColNames: map[string]struct{}{
+				"public.a.a": {},
+				"public.a.b": {},
+			},
 			expectedInputs: [][]string{{"999", "8"}},
 			expectedOutputs: []string{`select
  ├── scan a
@@ -82,7 +87,9 @@ func TestRunExplainCombinations(t *testing.T) {
 			}
 		}
 
-		inputs, outputs, err := getExplainCombinations(conn, "EXPLAIN(OPT)", test.placeholderToColMap, bundle)
+		inputs, outputs, err := getExplainCombinations(
+			conn, "EXPLAIN(OPT)", test.placeholderToColMap, test.placeholderFQColNames, bundle,
+		)
 		assert.NoError(t, err)
 		assert.Equal(t, test.expectedInputs, inputs)
 		assert.Equal(t, test.expectedOutputs, outputs)
diff --git a/pkg/sql/sem/tree/BUILD.bazel b/pkg/sql/sem/tree/BUILD.bazel
index e8dd40e5c1b5..a0893db3d7f6 100644
--- a/pkg/sql/sem/tree/BUILD.bazel
+++ b/pkg/sql/sem/tree/BUILD.bazel
@@ -174,6 +174,7 @@ go_test(
         "constant_test.go",
         "datum_integration_test.go",
         "datum_invariants_test.go",
+        "datum_prev_next_test.go",
         "datum_test.go",
         "expr_test.go",
         "format_test.go",
diff --git a/pkg/sql/sem/tree/datum.go b/pkg/sql/sem/tree/datum.go
index 3efd463354e2..9f92952592ff 100644
--- a/pkg/sql/sem/tree/datum.go
+++ b/pkg/sql/sem/tree/datum.go
@@ -1629,7 +1629,7 @@ func (d *DEncodedKey) Prev(ctx CompareContext) (Datum, bool) {
 
 // Next implements the Datum interface.
 func (d *DEncodedKey) Next(ctx CompareContext) (Datum, bool) {
-	return nil, true
+	return nil, false
 }
 
 // IsMax implements the Datum interface.
@@ -5794,3 +5794,120 @@ func AdjustValueToType(typ *types.T, inVal Datum) (outVal Datum, err error) {
 	}
 	return inVal, nil
 }
+
+// DatumPrev returns a datum that is "previous" to the given one. For many types
+// it just delegates to Datum.Prev, but for some types that don't have an
+// implementation of that function this method makes the best effort to come up
+// with a reasonable previous datum that is smaller than the given one.
+//
+// The return value is undefined if Datum.IsMin returns true or if the value is
+// NaN of an infinity (for floats and decimals).
+func DatumPrev(
+	datum Datum, cmpCtx CompareContext, collationEnv *CollationEnvironment,
+) (Datum, bool) {
+	datum = UnwrapDOidWrapper(datum)
+	prevString := func(s string) (string, bool) {
+		// In order to obtain a previous string we subtract 1 from the last
+		// non-zero byte.
+		b := []byte(s)
+		lastNonZeroByteIdx := len(b) - 1
+		for ; lastNonZeroByteIdx >= 0 && b[lastNonZeroByteIdx] == 0; lastNonZeroByteIdx-- {
+		}
+		if lastNonZeroByteIdx < 0 {
+			return "", false
+		}
+		b[lastNonZeroByteIdx]--
+		return string(b), true
+	}
+	switch d := datum.(type) {
+	case *DDecimal:
+		var prev DDecimal
+		var sub apd.Decimal
+		_, err := sub.SetFloat64(1e-6)
+		if err != nil {
+			return nil, false
+		}
+		_, err = ExactCtx.Sub(&prev.Decimal, &d.Decimal, &sub)
+		if err != nil {
+			return nil, false
+		}
+		return &prev, true
+	case *DString:
+		prev, ok := prevString(string(*d))
+		if !ok {
+			return nil, false
+		}
+		return NewDString(prev), true
+	case *DCollatedString:
+		prev, ok := prevString(d.Contents)
+		if !ok {
+			return nil, false
+		}
+		c, err := NewDCollatedString(prev, d.Locale, collationEnv)
+		if err != nil {
+			return nil, false
+		}
+		return c, true
+	case *DBytes:
+		prev, ok := prevString(string(*d))
+		if !ok {
+			return nil, false
+		}
+		return NewDBytes(DBytes(prev)), true
+	case *DInterval:
+		// Subtract 1ms.
+		prev := d.Sub(duration.MakeDuration(1000000 /* nanos */, 0 /* days */, 0 /* months */))
+		return NewDInterval(prev, types.DefaultIntervalTypeMetadata), true
+	default:
+		// TODO(yuzefovich): consider adding support for other datums that don't
+		// have Datum.Prev implementation (DBitArray, DGeography, DGeometry,
+		// DBox2D, DJSON, DArray).
+		return datum.Prev(cmpCtx)
+	}
+}
+
+// DatumNext returns a datum that is "next" to the given one. For many types it
+// just delegates to Datum.Next, but for some types that don't have an
+// implementation of that function this method makes the best effort to come up
+// with a reasonable next datum that is greater than the given one.
+//
+// The return value is undefined if Datum.IsMax returns true or if the value is
+// NaN of an infinity (for floats and decimals).
+func DatumNext(
+	datum Datum, cmpCtx CompareContext, collationEnv *CollationEnvironment,
+) (Datum, bool) {
+	datum = UnwrapDOidWrapper(datum)
+	switch d := datum.(type) {
+	case *DDecimal:
+		var next DDecimal
+		var add apd.Decimal
+		_, err := add.SetFloat64(1e-6)
+		if err != nil {
+			return nil, false
+		}
+		_, err = ExactCtx.Add(&next.Decimal, &d.Decimal, &add)
+		if err != nil {
+			return nil, false
+		}
+		return &next, true
+	case *DCollatedString:
+		s := NewDString(d.Contents)
+		next, ok := s.Next(cmpCtx)
+		if !ok {
+			return nil, false
+		}
+		c, err := NewDCollatedString(string(*next.(*DString)), d.Locale, collationEnv)
+		if err != nil {
+			return nil, false
+		}
+		return c, true
+	case *DInterval:
+		next := d.Add(duration.MakeDuration(1000000 /* nanos */, 0 /* days */, 0 /* months */))
+		return NewDInterval(next, types.DefaultIntervalTypeMetadata), true
+	default:
+		// TODO(yuzefovich): consider adding support for other datums that don't
+		// have Datum.Next implementation (DGeography, DGeometry, DBox2D,
+		// DJSON).
+		return datum.Next(cmpCtx)
+	}
+}
diff --git a/pkg/sql/sem/tree/datum_prev_next_test.go b/pkg/sql/sem/tree/datum_prev_next_test.go
new file mode 100644
index 000000000000..a53c4b34dcba
--- /dev/null
+++ b/pkg/sql/sem/tree/datum_prev_next_test.go
@@ -0,0 +1,66 @@
+// Copyright 2023 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 tree_test
+
+import (
+	"math"
+	"testing"
+
+	"github.com/cockroachdb/apd/v3"
+	"github.com/cockroachdb/cockroach/pkg/sql/randgen"
+	"github.com/cockroachdb/cockroach/pkg/sql/sem/eval"
+	"github.com/cockroachdb/cockroach/pkg/sql/sem/tree"
+	"github.com/cockroachdb/cockroach/pkg/util/leaktest"
+	"github.com/cockroachdb/cockroach/pkg/util/log"
+	"github.com/cockroachdb/cockroach/pkg/util/randutil"
+	"github.com/stretchr/testify/require"
+)
+
+// TestDatumPrevNext verifies that tree.DatumPrev and tree.DatumNext return
+// datums that are smaller and larger, respectively, than the given datum if
+// ok=true is returned (modulo some edge cases).
+func TestDatumPrevNext(t *testing.T) {
+	defer leaktest.AfterTest(t)()
+	defer log.Scope(t).Close(t)
+
+	rng, _ := randutil.NewTestRand()
+	var evalCtx eval.Context
+	const numRuns = 1000
+	for i := 0; i < numRuns; i++ {
+		typ := randgen.RandType(rng)
+		d := randgen.RandDatum(rng, typ, false /* nullOk */)
+		// Ignore NaNs and infinities.
+		if f, ok := d.(*tree.DFloat); ok {
+			if math.IsNaN(float64(*f)) || math.IsInf(float64(*f), 0) {
+				continue
+			}
+		}
+		if dec, ok := d.(*tree.DDecimal); ok {
+			if dec.Form == apd.NaN || dec.Form == apd.Infinite {
+				continue
+			}
+		}
+		if !d.IsMin(&evalCtx) {
+			if prev, ok := tree.DatumPrev(d, &evalCtx, &evalCtx.CollationEnv); ok {
+				cmp, err := d.CompareError(&evalCtx, prev)
+				require.NoError(t, err)
+				require.True(t, cmp > 0, "d=%s, prev=%s, type=%s", d.String(), prev.String(), d.ResolvedType().SQLString())
+			}
+		}
+		if !d.IsMax(&evalCtx) {
+			if next, ok := tree.DatumNext(d, &evalCtx, &evalCtx.CollationEnv); ok {
+				cmp, err := d.CompareError(&evalCtx, next)
+				require.NoError(t, err)
+				require.True(t, cmp < 0, "d=%s, next=%s, type=%s", d.String(), next.String(), d.ResolvedType().SQLString())
+			}
+		}
+	}
+}