diff --git a/moto/ssm/exceptions.py b/moto/ssm/exceptions.py
index f68e47029..0d2fdee3b 100644
--- a/moto/ssm/exceptions.py
+++ b/moto/ssm/exceptions.py
@@ -115,3 +115,12 @@ class DuplicateDocumentContent(JsonRESTError):
         super(DuplicateDocumentContent, self).__init__(
             "DuplicateDocumentContent", message
         )
+
+
+class ParameterMaxVersionLimitExceeded(JsonRESTError):
+    code = 400
+
+    def __init__(self, message):
+        super(ParameterMaxVersionLimitExceeded, self).__init__(
+            "ParameterMaxVersionLimitExceeded", message
+        )
diff --git a/moto/ssm/models.py b/moto/ssm/models.py
index 72e9b21e3..74f60e58a 100644
--- a/moto/ssm/models.py
+++ b/moto/ssm/models.py
@@ -32,9 +32,13 @@ from .exceptions import (
     InvalidDocumentVersion,
     DuplicateDocumentVersionName,
     DuplicateDocumentContent,
+    ParameterMaxVersionLimitExceeded,
 )
 
 
+PARAMETER_VERSION_LIMIT = 100
+
+
 class Parameter(BaseModel):
     def __init__(
         self,
@@ -1281,6 +1285,18 @@ class SimpleSystemManagerBackend(BaseBackend):
                         parameter.labels.remove(label)
         return [invalid_labels, version]
 
+    def _check_for_parameter_version_limit_exception(self, name):
+        # https://docs.aws.amazon.com/systems-manager/latest/userguide/sysman-paramstore-versions.html
+        parameter_versions = self._parameters[name]
+        oldest_parameter = parameter_versions[0]
+        if oldest_parameter.labels:
+            raise ParameterMaxVersionLimitExceeded(
+                "You attempted to create a new version of %s by calling the PutParameter API "
+                "with the overwrite flag. Version %d, the oldest version, can't be deleted "
+                "because it has a label associated with it. Move the label to another version "
+                "of the parameter, and try again." % (name, oldest_parameter.version)
+            )
+
     def put_parameter(
         self, name, description, value, type, allowed_pattern, keyid, overwrite, tags,
     ):
@@ -1317,6 +1333,10 @@ class SimpleSystemManagerBackend(BaseBackend):
             if not overwrite:
                 return
 
+            if len(previous_parameter_versions) >= PARAMETER_VERSION_LIMIT:
+                self._check_for_parameter_version_limit_exception(name)
+                previous_parameter_versions.pop(0)
+
         last_modified_date = time.time()
         self._parameters[name].append(
             Parameter(
diff --git a/tests/test_ssm/test_ssm_boto3.py b/tests/test_ssm/test_ssm_boto3.py
index 18b48456f..3301ed32c 100644
--- a/tests/test_ssm/test_ssm_boto3.py
+++ b/tests/test_ssm/test_ssm_boto3.py
@@ -12,6 +12,7 @@ from botocore.exceptions import ClientError
 import pytest
 
 from moto import mock_ec2, mock_ssm
+from moto.ssm.models import PARAMETER_VERSION_LIMIT
 from tests import EXAMPLE_AMI_ID
 
 
@@ -1755,3 +1756,56 @@ def test_get_command_invocations_by_instance_tag():
     for instance_id in instance_ids:
         resp = ssm.get_command_invocation(CommandId=command_id, InstanceId=instance_id)
         resp["Status"].should.equal("Success")
+
+
+@mock_ssm
+def test_parameter_version_limit():
+    client = boto3.client("ssm", region_name="us-east-1")
+    parameter_name = "test-param"
+    for i in range(PARAMETER_VERSION_LIMIT + 1):
+        client.put_parameter(
+            Name=parameter_name,
+            Value="value-%d" % (i + 1),
+            Type="String",
+            Overwrite=True,
+        )
+
+    paginator = client.get_paginator("get_parameter_history")
+    page_iterator = paginator.paginate(Name=parameter_name)
+    parameter_history = list(
+        item for page in page_iterator for item in page["Parameters"]
+    )
+
+    len(parameter_history).should.equal(PARAMETER_VERSION_LIMIT)
+    parameter_history[0]["Value"].should.equal("value-2")
+    latest_version_index = PARAMETER_VERSION_LIMIT - 1
+    latest_version_value = "value-%d" % (PARAMETER_VERSION_LIMIT + 1)
+    parameter_history[latest_version_index]["Value"].should.equal(latest_version_value)
+
+
+@mock_ssm
+def test_parameter_overwrite_fails_when_limit_reached_and_oldest_version_has_label():
+    client = boto3.client("ssm", region_name="us-east-1")
+    parameter_name = "test-param"
+    for i in range(PARAMETER_VERSION_LIMIT):
+        client.put_parameter(
+            Name=parameter_name,
+            Value="value-%d" % (i + 1),
+            Type="String",
+            Overwrite=True,
+        )
+    client.label_parameter_version(
+        Name=parameter_name, ParameterVersion=1, Labels=["test-label"]
+    )
+
+    with pytest.raises(ClientError) as ex:
+        client.put_parameter(
+            Name=parameter_name, Value="new-value", Type="String", Overwrite=True,
+        )
+    error = ex.value.response["Error"]
+    error["Code"].should.equal("ParameterMaxVersionLimitExceeded")
+    error["Message"].should.contain(parameter_name)
+    error["Message"].should.contain("Version 1")
+    error["Message"].should.match(
+        r"the oldest version, can't be deleted because it has a label associated with it. Move the label to another version of the parameter, and try again."
+    )