diff --git a/.changelog/23187.txt b/.changelog/23187.txt
new file mode 100644
index 000000000000..08ebac55a08a
--- /dev/null
+++ b/.changelog/23187.txt
@@ -0,0 +1,3 @@
+```release-note:enhancement
+resource/aws_autoscaling_group: Disable scale-in protection before draining instances
+```
\ No newline at end of file
diff --git a/internal/service/autoscaling/group.go b/internal/service/autoscaling/group.go
index 2789552436f3..6091a18687fc 100644
--- a/internal/service/autoscaling/group.go
+++ b/internal/service/autoscaling/group.go
@@ -1654,6 +1654,18 @@ func resourceGroupDrain(d *schema.ResourceData, meta interface{}) error {
 		return fmt.Errorf("Error setting capacity to zero to drain: %s", err)
 	}
 
+	// Next, ensure that instances are not prevented from scaling in.
+	//
+	// The ASG's own scale-in protection setting doesn't make a difference here,
+	// as it only affects new instances, which won't be launched now that the
+	// desired capacity is set to 0. There is also the possibility that this ASG
+	// no longer applies scale-in protection to new instances, but there's still
+	// old ones that have it.
+	log.Printf("[DEBUG] Disabling scale-in protection for all instances in the group")
+	if err := disableASGScaleInProtections(d, conn); err != nil {
+		return fmt.Errorf("Error disabling scale-in protection for all instances: %s", err)
+	}
+
 	// Next, wait for the Auto Scaling Group to drain
 	log.Printf("[DEBUG] Waiting for group to have zero instances")
 	var g *autoscaling.Group
@@ -2365,3 +2377,40 @@ func flattenLaunchTemplateSpecification(lt *autoscaling.LaunchTemplateSpecificat
 
 	return result
 }
+
+// disableASGScaleInProtections disables scale-in protection for all instances
+// in the given Auto-Scaling Group.
+func disableASGScaleInProtections(d *schema.ResourceData, conn *autoscaling.AutoScaling) error {
+	g, err := getGroup(d.Id(), conn)
+	if err != nil {
+		return fmt.Errorf("Error getting group %s: %s", d.Id(), err)
+	}
+
+	var instanceIds []string
+	for _, instance := range g.Instances {
+		if aws.BoolValue(instance.ProtectedFromScaleIn) {
+			instanceIds = append(instanceIds, aws.StringValue(instance.InstanceId))
+		}
+	}
+
+	const chunkSize = 50 // API limit
+
+	for i := 0; i < len(instanceIds); i += chunkSize {
+		j := i + chunkSize
+		if j > len(instanceIds) {
+			j = len(instanceIds)
+		}
+
+		input := autoscaling.SetInstanceProtectionInput{
+			AutoScalingGroupName: aws.String(d.Id()),
+			InstanceIds:          aws.StringSlice(instanceIds[i:j]),
+			ProtectedFromScaleIn: aws.Bool(false),
+		}
+
+		if _, err := conn.SetInstanceProtection(&input); err != nil {
+			return fmt.Errorf("Error disabling scale-in protections: %s", err)
+		}
+	}
+
+	return nil
+}
diff --git a/internal/service/autoscaling/group_test.go b/internal/service/autoscaling/group_test.go
index 9a73980219a0..e347e1249527 100644
--- a/internal/service/autoscaling/group_test.go
+++ b/internal/service/autoscaling/group_test.go
@@ -2306,6 +2306,33 @@ func TestAccAutoScalingGroup_launchTempPartitionNum(t *testing.T) {
 	})
 }
 
+func TestAccAutoScalingGroup_Destroy_whenProtectedFromScaleIn(t *testing.T) {
+	var group autoscaling.Group
+	rName := fmt.Sprintf("terraform-test-%s", sdkacctest.RandString(10))
+	resourceName := "aws_autoscaling_group.test"
+
+	resource.ParallelTest(t, resource.TestCase{
+		PreCheck:     func() { acctest.PreCheck(t) },
+		ErrorCheck:   acctest.ErrorCheck(t, autoscaling.EndpointsID),
+		Providers:    acctest.Providers,
+		CheckDestroy: testAccCheckGroupDestroy,
+		Steps: []resource.TestStep{
+			{
+				Config: testAccGroupConfig_DestroyWhenProtectedFromScaleIn_beforeDestroy(rName),
+				Check: resource.ComposeTestCheckFunc(
+					testAccCheckGroupExists(resourceName, &group),
+					testAccCheckGroupHealthyCapacity(&group, 2),
+					resource.TestCheckResourceAttr(resourceName, "protect_from_scale_in", "true"),
+				),
+			},
+			{
+				Config: testAccGroupConfig_DestroyWhenProtectedFromScaleIn_afterDestroy(),
+				// Reaching this step is good enough, as it indicates the ASG was destroyed successfully.
+			},
+		},
+	})
+}
+
 func testAccGroupNameGeneratedConfig() string {
 	return acctest.ConfigCompose(
 		acctest.ConfigAvailableAZsNoOptInDefaultExclude(),
@@ -4776,6 +4803,56 @@ resource "aws_autoscaling_group" "test" {
 `
 }
 
+func testAccGroupConfig_DestroyWhenProtectedFromScaleIn_beforeDestroy(name string) string {
+	return acctest.ConfigAvailableAZsNoOptInDefaultExclude() +
+		fmt.Sprintf(`
+data "aws_ami" "test" {
+  most_recent = true
+  owners      = ["amazon"]
+
+  filter {
+    name   = "name"
+    values = ["amzn-ami-hvm-*-x86_64-gp2"]
+  }
+}
+
+resource "aws_launch_configuration" "test" {
+  image_id      = data.aws_ami.test.id
+  instance_type = "t3.micro"
+}
+
+resource "aws_autoscaling_group" "test" {
+  availability_zones    = [data.aws_availability_zones.available.names[0]]
+  name                  = %[1]q
+  max_size              = 2
+  min_size              = 2
+  desired_capacity      = 2
+  protect_from_scale_in = true
+  launch_configuration  = aws_launch_configuration.test.name
+}
+`, name)
+}
+
+func testAccGroupConfig_DestroyWhenProtectedFromScaleIn_afterDestroy() string {
+	return acctest.ConfigAvailableAZsNoOptInDefaultExclude() +
+		`
+data "aws_ami" "test" {
+  most_recent = true
+  owners      = ["amazon"]
+
+  filter {
+    name   = "name"
+    values = ["amzn-ami-hvm-*-x86_64-gp2"]
+  }
+}
+
+resource "aws_launch_configuration" "test" {
+  image_id      = data.aws_ami.test.id
+  instance_type = "t3.micro"
+}
+`
+}
+
 func testAccCheckAutoScalingInstanceRefreshCount(group *autoscaling.Group, expected int) resource.TestCheckFunc {
 	return func(state *terraform.State) error {
 		conn := acctest.Provider.Meta().(*conns.AWSClient).AutoScalingConn