diff --git a/expression/BUILD.bazel b/expression/BUILD.bazel
index fc1752ef19e63..c7304642c544a 100644
--- a/expression/BUILD.bazel
+++ b/expression/BUILD.bazel
@@ -111,6 +111,7 @@ go_library(
         "@com_github_pingcap_errors//:errors",
         "@com_github_pingcap_failpoint//:failpoint",
         "@com_github_pingcap_tipb//go-tipb",
+        "@com_github_pkg_errors//:errors",
         "@com_github_tikv_client_go_v2//oracle",
         "@org_golang_x_exp//slices",
         "@org_golang_x_tools//container/intsets",
diff --git a/expression/builtin_compare.go b/expression/builtin_compare.go
index 3baa86b635ba6..4411f4b6b90ff 100644
--- a/expression/builtin_compare.go
+++ b/expression/builtin_compare.go
@@ -28,6 +28,7 @@ import (
 	"github.com/pingcap/tidb/util/chunk"
 	"github.com/pingcap/tidb/util/collate"
 	"github.com/pingcap/tipb/go-tipb"
+	"github.com/pkg/errors"
 )
 
 var (
@@ -1575,6 +1576,11 @@ func (c *compareFunctionClass) refineArgs(ctx sessionctx.Context, args []Express
 		// here and skip this refine operation in all other cases for safety.
 		if (arg0IsInt && !arg0IsCon && arg1IsString && arg1IsCon) || (arg1IsInt && !arg1IsCon && arg0IsString && arg0IsCon) {
 			ctx.GetSessionVars().StmtCtx.SkipPlanCache = true
+			if arg1IsString {
+				ctx.GetSessionVars().StmtCtx.AppendWarning(errors.Errorf("skip plan-cache: '%v' may be converted to INT", arg1.String()))
+			} else { // arg0IsString
+				ctx.GetSessionVars().StmtCtx.AppendWarning(errors.Errorf("skip plan-cache: '%v' may be converted to INT", arg0.String()))
+			}
 			RemoveMutableConst(ctx, args)
 		} else {
 			return args
diff --git a/expression/builtin_other.go b/expression/builtin_other.go
index 0f4bd85d45b43..c62278c2bd101 100644
--- a/expression/builtin_other.go
+++ b/expression/builtin_other.go
@@ -166,6 +166,7 @@ func (c *inFunctionClass) verifyArgs(ctx sessionctx.Context, args []Expression)
 				if constant.Value.GetInt64() < 0 {
 					if MaybeOverOptimized4PlanCache(ctx, args) {
 						ctx.GetSessionVars().StmtCtx.SkipPlanCache = true
+						ctx.GetSessionVars().StmtCtx.AppendWarning(errors.Errorf("skip plan-cache: Bit Column in (%v)", constant.Value.GetInt64()))
 					}
 					continue
 				}
diff --git a/planner/core/expression_rewriter.go b/planner/core/expression_rewriter.go
index 522dedacca24a..d0ca6e6f8e4cf 100644
--- a/planner/core/expression_rewriter.go
+++ b/planner/core/expression_rewriter.go
@@ -1554,6 +1554,7 @@ func (er *expressionRewriter) inToExpression(lLen int, not bool, tp *types.Field
 						// To keep the result be compatible with MySQL, refine `int non-constant <cmp> str constant`
 						// here and skip this refine operation in all other cases for safety.
 						er.sctx.GetSessionVars().StmtCtx.SkipPlanCache = true
+						er.sctx.GetSessionVars().StmtCtx.AppendWarning(errors.Errorf("skip plan-cache: '%v' may be converted to INT", c.String()))
 						expression.RemoveMutableConst(er.sctx, []expression.Expression{c})
 					} else {
 						continue
diff --git a/planner/core/find_best_task.go b/planner/core/find_best_task.go
index 52eab05629d59..12f298e6cd2ba 100644
--- a/planner/core/find_best_task.go
+++ b/planner/core/find_best_task.go
@@ -903,6 +903,7 @@ func (ds *DataSource) findBestTask(prop *property.PhysicalProperty, planCounter
 			// We should uncache the tableDual plan.
 			if expression.MaybeOverOptimized4PlanCache(ds.ctx, path.AccessConds) {
 				ds.ctx.GetSessionVars().StmtCtx.SkipPlanCache = true
+				ds.ctx.GetSessionVars().StmtCtx.AppendWarning(errors.Errorf("skip plan-cache: get a TableDual plan"))
 			}
 			dual := PhysicalTableDual{}.Init(ds.ctx, ds.stats, ds.blockOffset)
 			dual.SetSchema(ds.schema)
diff --git a/planner/core/integration_test.go b/planner/core/integration_test.go
index f9c58ace525f8..ce4b299cdf328 100644
--- a/planner/core/integration_test.go
+++ b/planner/core/integration_test.go
@@ -7781,7 +7781,10 @@ func TestPlanCacheForTableRangeFallback(t *testing.T) {
 	tk.MustExec("prepare stmt from 'select * from t where a in (?, ?, ?, ?, ?) and b > 1'")
 	tk.MustExec("set @a=10, @b=20, @c=30, @d=40, @e=50")
 	tk.MustExec("execute stmt using @a, @b, @c, @d, @e")
-	tk.MustQuery("show warnings").Check(testkit.Rows("Warning 1105 Memory capacity of 10 bytes for 'tidb_opt_range_max_size' exceeded when building ranges. Less accurate ranges such as full range are chosen"))
+	tk.MustQuery("show warnings").Sort().Check(testkit.Rows("Warning 1105 Memory capacity of 10 bytes for 'tidb_opt_range_max_size' exceeded when building ranges. Less accurate ranges such as full range are chosen",
+		"Warning 1105 skip plan-cache: in-list is too long",
+		"Warning 1105 skip plan-cache: in-list is too long",
+		"Warning 1105 skip plan-cache: in-list is too long"))
 	tk.MustExec("execute stmt using @a, @b, @c, @d, @e")
 	// The plan with range fallback is not cached.
 	tk.MustQuery("select @@last_plan_from_cache").Check(testkit.Rows("0"))
@@ -7828,7 +7831,9 @@ func TestPlanCacheForIndexRangeFallback(t *testing.T) {
 	tk.MustExec("prepare stmt2 from 'select * from t where a in (?, ?, ?, ?, ?) and b in (?, ?, ?, ?, ?)'")
 	tk.MustExec("set @a='aa', @b='bb', @c='cc', @d='dd', @e='ee', @f='ff', @g='gg', @h='hh', @i='ii', @j='jj'")
 	tk.MustExec("execute stmt2 using @a, @b, @c, @d, @e, @f, @g, @h, @i, @j")
-	tk.MustQuery("show warnings").Check(testkit.Rows("Warning 1105 Memory capacity of 1330 bytes for 'tidb_opt_range_max_size' exceeded when building ranges. Less accurate ranges such as full range are chosen"))
+	tk.MustQuery("show warnings").Sort().Check(testkit.Rows("Warning 1105 Memory capacity of 1330 bytes for 'tidb_opt_range_max_size' exceeded when building ranges. Less accurate ranges such as full range are chosen",
+		"Warning 1105 skip plan-cache: in-list is too long",
+		"Warning 1105 skip plan-cache: in-list is too long"))
 	tk.MustExec("execute stmt2 using @a, @b, @c, @d, @e, @f, @g, @h, @i, @j")
 	tk.MustQuery("select @@last_plan_from_cache").Check(testkit.Rows("0"))
 }
@@ -7984,7 +7989,12 @@ func TestPlanCacheForIndexJoinRangeFallback(t *testing.T) {
 	tk.MustExec("prepare stmt2 from 'select /*+ inl_join(t1) */ * from  t1 join t2 on t1.a = t2.d where t1.b in (?, ?, ?, ?, ?)'")
 	tk.MustExec("set @a='a', @b='b', @c='c', @d='d', @e='e'")
 	tk.MustExec("execute stmt2 using @a, @b, @c, @d, @e")
-	tk.MustQuery("show warnings").Check(testkit.Rows("Warning 1105 Memory capacity of 1275 bytes for 'tidb_opt_range_max_size' exceeded when building ranges. Less accurate ranges such as full range are chosen"))
+	tk.MustQuery("show warnings").Sort().Check(testkit.Rows("Warning 1105 Memory capacity of 1275 bytes for 'tidb_opt_range_max_size' exceeded when building ranges. Less accurate ranges such as full range are chosen",
+		"Warning 1105 skip plan-cache: in-list is too long",
+		"Warning 1105 skip plan-cache: in-list is too long",
+		"Warning 1105 skip plan-cache: in-list is too long",
+		"Warning 1105 skip plan-cache: in-list is too long",
+		"Warning 1105 skip plan-cache: in-list is too long"))
 	tk.MustExec("execute stmt2 using @a, @b, @c, @d, @e")
 	tk.MustQuery("select @@last_plan_from_cache").Check(testkit.Rows("0"))
 }
diff --git a/planner/core/optimizer.go b/planner/core/optimizer.go
index d96f70462cc33..8b281cbc1b7cb 100644
--- a/planner/core/optimizer.go
+++ b/planner/core/optimizer.go
@@ -668,6 +668,7 @@ func setupFineGrainedShuffleInternal(plan PhysicalPlan, helper *fineGrainedShuff
 func checkPlanCacheable(sctx sessionctx.Context, plan PhysicalPlan) {
 	if sctx.GetSessionVars().StmtCtx.UseCache && useTiFlash(plan) {
 		sctx.GetSessionVars().StmtCtx.SkipPlanCache = true
+		sctx.GetSessionVars().StmtCtx.AppendWarning(errors.Errorf("skip plan-cache: TiFlash plan is un-cacheable"))
 	}
 }
 
diff --git a/planner/core/plan_cache_test.go b/planner/core/plan_cache_test.go
index d1f51bc296c07..868f35229ce6e 100644
--- a/planner/core/plan_cache_test.go
+++ b/planner/core/plan_cache_test.go
@@ -176,3 +176,35 @@ func TestIssue38710(t *testing.T) {
 	require.Equal(t, 2, len(rows.Rows()))
 	tk.MustQuery("select @@last_plan_from_cache").Check(testkit.Rows("0")) // can not use the cache because the types for @a and @b are not equal to the cached plan
 }
+
+func TestPlanCacheDiagInfo(t *testing.T) {
+	store := testkit.CreateMockStore(t)
+	tk := testkit.NewTestKit(t, store)
+	tk.MustExec("use test")
+	tk.MustExec("create table t (a int, b int, key(a), key(b))")
+
+	tk.MustExec("prepare stmt from 'select * from t where a in (select a from t)'")
+	tk.MustQuery("show warnings").Check(testkit.Rows("Warning 1105 skip plan-cache: query has sub-queries is un-cacheable"))
+
+	tk.MustExec("prepare stmt from 'select /*+ ignore_plan_cache() */ * from t'")
+	tk.MustQuery("show warnings").Check(testkit.Rows("Warning 1105 skip plan-cache: ignore plan cache by hint"))
+
+	tk.MustExec("prepare stmt from 'select * from t limit ?'")
+	tk.MustQuery("show warnings").Check(testkit.Rows("Warning 1105 skip plan-cache: query has 'limit ?' is un-cacheable"))
+
+	tk.MustExec("prepare stmt from 'select * from t limit ?, 1'")
+	tk.MustQuery("show warnings").Check(testkit.Rows("Warning 1105 skip plan-cache: query has 'limit ?, 10' is un-cacheable"))
+
+	tk.MustExec("prepare stmt from 'select * from t order by ?'")
+	tk.MustQuery("show warnings").Check(testkit.Rows("Warning 1105 skip plan-cache: query has 'order by ?' is un-cacheable"))
+
+	tk.MustExec("prepare stmt from 'select * from t where a=?'")
+	tk.MustExec("set @a='123'")
+	tk.MustExec("execute stmt using @a") // '123' -> 123
+	tk.MustQuery("show warnings").Check(testkit.Rows("Warning 1105 skip plan-cache: '123' may be converted to INT"))
+
+	tk.MustExec("prepare stmt from 'select * from t where a=? and a=?'")
+	tk.MustExec("set @a=1, @b=1")
+	tk.MustExec("execute stmt using @a, @b") // a=1 and a=1 -> a=1
+	tk.MustQuery("show warnings").Check(testkit.Rows("Warning 1105 skip plan-cache: some parameters may be overwritten"))
+}
diff --git a/planner/core/plan_cache_utils.go b/planner/core/plan_cache_utils.go
index 0abecafaf7ec8..4229e2b134f06 100644
--- a/planner/core/plan_cache_utils.go
+++ b/planner/core/plan_cache_utils.go
@@ -117,7 +117,11 @@ func GeneratePlanCacheStmtWithAST(ctx context.Context, sctx sessionctx.Context,
 	if !vars.EnablePreparedPlanCache {
 		prepared.UseCache = false
 	} else {
-		prepared.UseCache = CacheableWithCtx(sctx, stmt, ret.InfoSchema)
+		cacheable, reason := CacheableWithCtx(sctx, stmt, ret.InfoSchema)
+		prepared.UseCache = cacheable
+		if !cacheable {
+			sctx.GetSessionVars().StmtCtx.AppendWarning(errors.Errorf("skip plan-cache: " + reason))
+		}
 		selectStmtNode, normalizedSQL4PC, digest4PC, err = ExtractSelectAndNormalizeDigest(stmt, vars.CurrentDB)
 		if err != nil || selectStmtNode == nil {
 			normalizedSQL4PC = ""
diff --git a/planner/core/plan_cacheable_checker.go b/planner/core/plan_cacheable_checker.go
index 0e4e28250ad4c..55b1e45cd0e99 100644
--- a/planner/core/plan_cacheable_checker.go
+++ b/planner/core/plan_cacheable_checker.go
@@ -15,6 +15,8 @@
 package core
 
 import (
+	"fmt"
+
 	"github.com/pingcap/tidb/expression"
 	"github.com/pingcap/tidb/infoschema"
 	"github.com/pingcap/tidb/parser/ast"
@@ -27,20 +29,21 @@ import (
 
 // Cacheable checks whether the input ast is cacheable with empty session context, which is mainly for testing.
 func Cacheable(node ast.Node, is infoschema.InfoSchema) bool {
-	return CacheableWithCtx(nil, node, is)
+	c, _ := CacheableWithCtx(nil, node, is)
+	return c
 }
 
 // CacheableWithCtx checks whether the input ast is cacheable.
 // Handle "ignore_plan_cache()" hint
 // If there are multiple hints, only one will take effect
-func CacheableWithCtx(sctx sessionctx.Context, node ast.Node, is infoschema.InfoSchema) bool {
+func CacheableWithCtx(sctx sessionctx.Context, node ast.Node, is infoschema.InfoSchema) (bool, string) {
 	_, isSelect := node.(*ast.SelectStmt)
 	_, isUpdate := node.(*ast.UpdateStmt)
 	_, isInsert := node.(*ast.InsertStmt)
 	_, isDelete := node.(*ast.DeleteStmt)
 	_, isSetOpr := node.(*ast.SetOprStmt)
 	if !(isSelect || isUpdate || isInsert || isDelete || isSetOpr) {
-		return false
+		return false, "not a SELECT/UPDATE/INSERT/DELETE/SET statement"
 	}
 	checker := cacheableChecker{
 		sctx:      sctx,
@@ -48,7 +51,7 @@ func CacheableWithCtx(sctx sessionctx.Context, node ast.Node, is infoschema.Info
 		schema:    is,
 	}
 	node.Accept(&checker)
-	return checker.cacheable
+	return checker.cacheable, checker.reason
 }
 
 // cacheableChecker checks whether a query's plan can be cached, querys that:
@@ -61,6 +64,7 @@ type cacheableChecker struct {
 	sctx      sessionctx.Context
 	cacheable bool
 	schema    infoschema.InfoSchema
+	reason    string // reason why cannot use plan-cache
 }
 
 // Enter implements Visitor interface.
@@ -70,6 +74,7 @@ func (checker *cacheableChecker) Enter(in ast.Node) (out ast.Node, skipChildren
 		for _, hints := range node.TableHints {
 			if hints.HintName.L == HintIgnorePlanCache {
 				checker.cacheable = false
+				checker.reason = "ignore plan cache by hint"
 				return in, true
 			}
 		}
@@ -77,6 +82,7 @@ func (checker *cacheableChecker) Enter(in ast.Node) (out ast.Node, skipChildren
 		for _, hints := range node.TableHints {
 			if hints.HintName.L == HintIgnorePlanCache {
 				checker.cacheable = false
+				checker.reason = "ignore plan cache by hint"
 				return in, true
 			}
 		}
@@ -84,21 +90,25 @@ func (checker *cacheableChecker) Enter(in ast.Node) (out ast.Node, skipChildren
 		for _, hints := range node.TableHints {
 			if hints.HintName.L == HintIgnorePlanCache {
 				checker.cacheable = false
+				checker.reason = "ignore plan cache by hint"
 				return in, true
 			}
 		}
 	case *ast.VariableExpr, *ast.ExistsSubqueryExpr, *ast.SubqueryExpr:
 		checker.cacheable = false
+		checker.reason = "query has sub-queries is un-cacheable"
 		return in, true
 	case *ast.FuncCallExpr:
 		if _, found := expression.UnCacheableFunctions[node.FnName.L]; found {
 			checker.cacheable = false
+			checker.reason = fmt.Sprintf("query has '%v' is un-cacheable", node.FnName.L)
 			return in, true
 		}
 	case *ast.OrderByClause:
 		for _, item := range node.Items {
 			if _, isParamMarker := item.Expr.(*driver.ParamMarkerExpr); isParamMarker {
 				checker.cacheable = false
+				checker.reason = "query has 'order by ?' is un-cacheable"
 				return in, true
 			}
 		}
@@ -106,6 +116,7 @@ func (checker *cacheableChecker) Enter(in ast.Node) (out ast.Node, skipChildren
 		for _, item := range node.Items {
 			if _, isParamMarker := item.Expr.(*driver.ParamMarkerExpr); isParamMarker {
 				checker.cacheable = false
+				checker.reason = "query has 'group by ?' is un-cacheable"
 				return in, true
 			}
 		}
@@ -113,18 +124,21 @@ func (checker *cacheableChecker) Enter(in ast.Node) (out ast.Node, skipChildren
 		if node.Count != nil {
 			if _, isParamMarker := node.Count.(*driver.ParamMarkerExpr); isParamMarker {
 				checker.cacheable = false
+				checker.reason = "query has 'limit ?' is un-cacheable"
 				return in, true
 			}
 		}
 		if node.Offset != nil {
 			if _, isParamMarker := node.Offset.(*driver.ParamMarkerExpr); isParamMarker {
 				checker.cacheable = false
+				checker.reason = "query has 'limit ?, 10' is un-cacheable"
 				return in, true
 			}
 		}
 	case *ast.FrameBound:
 		if _, ok := node.Expr.(*driver.ParamMarkerExpr); ok {
 			checker.cacheable = false
+			checker.reason = "query has ? in window function frames is un-cacheable"
 			return in, true
 		}
 	case *ast.TableName:
@@ -138,14 +152,17 @@ func (checker *cacheableChecker) Enter(in ast.Node) (out ast.Node, skipChildren
 					}
 				*/
 				checker.cacheable = false
+				checker.reason = "query accesses partitioned tables is un-cacheable"
 				return in, true
 			}
 			if hasGeneratedCol(checker.schema, node) {
 				checker.cacheable = false
+				checker.reason = "query accesses generated columns is un-cacheable"
 				return in, true
 			}
 			if isTempTable(checker.schema, node) {
 				checker.cacheable = false
+				checker.reason = "query accesses temporary tables is un-cacheable"
 				return in, true
 			}
 		}
diff --git a/sessionctx/stmtctx/stmtctx.go b/sessionctx/stmtctx/stmtctx.go
index c8fdc2ce32f2e..ec30fcb5fee35 100644
--- a/sessionctx/stmtctx/stmtctx.go
+++ b/sessionctx/stmtctx/stmtctx.go
@@ -1093,6 +1093,9 @@ func (sc *StatementContext) RecordRangeFallback(rangeMaxSize int64) {
 	// If range fallback happens, it means ether the query is unreasonable(for example, several long IN lists) or tidb_opt_range_max_size is too small
 	// and the generated plan is probably suboptimal. In that case we don't put it into plan cache.
 	sc.SkipPlanCache = true
+	if sc.UseCache {
+		sc.AppendWarning(errors.Errorf("skip plan-cache: in-list is too long"))
+	}
 	if !sc.RangeFallback {
 		sc.AppendWarning(errors.Errorf("Memory capacity of %v bytes for 'tidb_opt_range_max_size' exceeded when building ranges. Less accurate ranges such as full range are chosen", rangeMaxSize))
 		sc.RangeFallback = true
diff --git a/util/ranger/detacher.go b/util/ranger/detacher.go
index cbeed5b6364de..596d27c27d9d8 100644
--- a/util/ranger/detacher.go
+++ b/util/ranger/detacher.go
@@ -623,6 +623,7 @@ func ExtractEqAndInCondition(sctx sessionctx.Context, conditions []expression.Ex
 			if expression.MaybeOverOptimized4PlanCache(sctx, conditions) {
 				// `a=@x and a=@y` --> `a=@x if @x==@y`
 				sctx.GetSessionVars().StmtCtx.SkipPlanCache = true
+				sctx.GetSessionVars().StmtCtx.AppendWarning(errors.Errorf("skip plan-cache: some parameters may be overwritten"))
 			}
 		}
 	}