diff --git a/op.c b/op.c
index 62bb4c3b9b91..5685fb26c837 100644
--- a/op.c
+++ b/op.c
@@ -5011,6 +5011,38 @@ S_fold_constants(pTHX_ OP *const o)
         break;
     case OP_REPEAT:
         if (o->op_private & OPpREPEAT_DOLIST) goto nope;
+        /* Croak if the string is going to be unrealistically
+         * large. (GH#13324) Otherwise, don't constant fold
+         * above a certain threshold. (GH#13793 & GH#20586)
+         *
+         * Implementation note: pp_pow returns powers of 2 as an NV
+         *     e.g. my $x = "A" x (2**3);
+         */
+        if (OP_TYPE_IS(cBINOPo->op_last, OP_CONST)) {
+            SV *constsv = cSVOPx_sv(cBINOPo->op_last);
+            UV arbitrary = 1024 * 1024;
+
+            if (SvIOKp(constsv)) {
+                if (SvIOK_UV(constsv)) {
+                    if (SvUVX(constsv) > SIZE_MAX >> 2)
+                        ck_warner(packWARN(WARN_MISC), "Unrealistically large string repetition value");
+                    if (SvUVX(constsv) > arbitrary)
+                        goto nope;
+                } else {
+                    if (SvIVX(constsv) > (IV)(SIZE_MAX >> 2))
+                        ck_warner(packWARN(WARN_MISC), "Unrealistically large string repetition value");
+                    if (SvIVX(constsv) > (IV)arbitrary)
+                        goto nope;
+                }
+            } else {
+                NV rhs = 0.0; rhs = SvNV_nomg(constsv);
+                if (rhs >= (NV)((SIZE_MAX >> 2) +1) ) {
+                    ck_warner(packWARN(WARN_MISC), "Unrealistically large string repetition value");
+                }
+                if (rhs > (NV)arbitrary)
+                    goto nope;
+            }
+        }
         break;
     case OP_SREFGEN:
         if (cUNOPx(cUNOPo->op_first)->op_first->op_type != OP_CONST
diff --git a/pod/perldiag.pod b/pod/perldiag.pod
index 082391b65b2e..7f92714712d0 100644
--- a/pod/perldiag.pod
+++ b/pod/perldiag.pod
@@ -7385,6 +7385,18 @@ reserved word.  It's best to put such a word in quotes, or capitalize it
 somehow, or insert an underbar into it.  You might also declare it as a
 subroutine.
 
+=item Unrealistically large string repetition value
+
+(W misc) The value of the right operand in the string repetition operator is
+likely close to or will exceed the maximum memory allocation that
+your system can provide.
+
+Even if an allocation of this size does succeed, subsequent string
+copies may still result in an out-of-memory condition.
+
+Note that a smaller memory constraint might be imposed on your
+application under C<ulimit>, if containerized, or other local configuration.
+
 =item Unrecognized character %s; marked by S<<-- HERE> after %s near column
 %d
 
diff --git a/t/op/repeat.t b/t/op/repeat.t
index fa7ce0690433..285fc94dfbf1 100644
--- a/t/op/repeat.t
+++ b/t/op/repeat.t
@@ -6,7 +6,7 @@ BEGIN {
     set_up_inc( '../lib' );
 }
 
-plan(tests => 50);
+plan(tests => 51);
 
 # compile time
 
@@ -193,6 +193,14 @@ fresh_perl_like(
 eval q{() = (() or ((0) x 0)); 1};
 is($@, "", "RT #130247");
 
+# [GH #13324] Perl croaks if a string repetition seems unsupportable
+fresh_perl_like(
+ 'use warnings; my $x = "A" x (2**99)',
+  qr/Unrealistically large string repetition/,
+  {stderr => 1},
+ 'Warn on unrealistically large string repetition',
+);
+
 # yes, the newlines matter
 fresh_perl_is(<<'PERL', "", { stderr => 1 }, "(perl #133778) MARK mishandling");
 map{s[][];eval;0}<DATA>__END__
diff --git a/t/perf/opcount.t b/t/perf/opcount.t
index dd16447bae1c..4b6ae3de1a0f 100644
--- a/t/perf/opcount.t
+++ b/t/perf/opcount.t
@@ -1245,4 +1245,11 @@ test_opcount(0, "Empty else{} blocks are optimised away",
                     stub => 0
                 });
 
+# GH #13793, GH #20586
+test_opcount(0, "Don't fold string repetition once deeemed too large",
+                sub { my $x = "A" x (2**22) },
+                {
+                    repeat      => 1,
+                });
+
 done_testing();