diff --git a/CHANGELOG.md b/CHANGELOG.md
index 6d0b53e3710..52b5dcfb14a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -42,6 +42,7 @@ The types of changes are:
 ### Fixed
 - Fixed bug with unescaped table names in mysql queries [#5072](https://github.com/ethyca/fides/pull/5072/)
 - Fixed bug with unresponsive messaging ui [#5081](https://github.com/ethyca/fides/pull/5081/)
+- Fixed FidesKey constructor bugs in CLI [#5113](https://github.com/ethyca/fides/pull/5113)
 
 
 ## [2.40.0](https://github.com/ethyca/fides/compare/2.39.2...2.40.0)
diff --git a/src/fides/core/annotate_dataset.py b/src/fides/core/annotate_dataset.py
index 920fd405fe1..bc2541dc8bd 100644
--- a/src/fides/core/annotate_dataset.py
+++ b/src/fides/core/annotate_dataset.py
@@ -82,7 +82,7 @@ def get_data_categories_annotation(
                 dataset_member, valid_categories
             )
 
-    return [FidesKey(value) for value in user_response]
+    return [str(FidesKey(value)) for value in user_response]  # type: ignore
 
 
 def annotate_dataset(
diff --git a/src/fides/core/dataset.py b/src/fides/core/dataset.py
index 9520273d842..fc28ccd823f 100644
--- a/src/fides/core/dataset.py
+++ b/src/fides/core/dataset.py
@@ -140,8 +140,10 @@ def make_dataset_key_unique(
     to avoid naming collisions.
     """
 
-    dataset.fides_key = FidesKey(
-        generate_unique_fides_key(dataset.fides_key, database_host, database_name)
+    dataset.fides_key = str(  # type: ignore
+        FidesKey(
+            generate_unique_fides_key(dataset.fides_key, database_host, database_name)
+        )
     )
     dataset.meta = {"database_host": database_host, "database_name": database_name}
     return dataset
diff --git a/tests/ctl/cli/test_cli.py b/tests/ctl/cli/test_cli.py
index ca3339b4971..86679e44d6b 100644
--- a/tests/ctl/cli/test_cli.py
+++ b/tests/ctl/cli/test_cli.py
@@ -4,7 +4,9 @@
 from json import dump, loads
 from typing import Generator
 
+import click
 import pytest
+import yaml
 from click.testing import CliRunner
 from git.repo import Repo
 from py._path.local import LocalPath
@@ -217,6 +219,61 @@ def test_pull_all(
         assert result.exit_code == 0
 
 
+@pytest.mark.integration
+class TestAnnotate:
+
+    def test_annotate(
+        self,
+        test_config_path: str,
+        test_cli_runner: CliRunner,
+    ) -> None:
+        """
+        Test annotating dataset allowing you to interactively annotate the dataset with data categories
+        """
+        with open(
+            "tests/ctl/data/dataset_missing_categories.yml", "r"
+        ) as current_dataset_yml:
+            dataset_yml = yaml.safe_load(current_dataset_yml)
+            # Confirm starting state, that the first field has no data categories
+            assert (
+                "data_categories"
+                not in dataset_yml["dataset"][0]["collections"][0]["fields"][0]
+            )
+
+        result = test_cli_runner.invoke(
+            cli,
+            [
+                "-f",
+                test_config_path,
+                "annotate",
+                "dataset",
+                "tests/ctl/data/dataset_missing_categories.yml",
+            ],
+            input="user\n",
+        )
+        print(result.output)
+        with open("tests/ctl/data/dataset_missing_categories.yml", "r") as dataset_yml:
+            # Helps assert that the data category was output correctly
+            dataset_yml = yaml.safe_load(dataset_yml)
+            assert dataset_yml["dataset"][0]["collections"][0]["fields"][0][
+                "data_categories"
+            ] == ["user"]
+
+            # Now remove the data category that was written by annotate dataset
+            del dataset_yml["dataset"][0]["collections"][0]["fields"][0][
+                "data_categories"
+            ]
+
+        with open(
+            "tests/ctl/data/dataset_missing_categories.yml", "w"
+        ) as current_dataset_yml:
+            # Restore the original contents to the file
+            yaml.safe_dump(dataset_yml, current_dataset_yml)
+
+        assert result.exit_code == 0
+        print(result.output)
+
+
 @pytest.mark.integration
 def test_audit(test_config_path: str, test_cli_runner: CliRunner) -> None:
     result = test_cli_runner.invoke(cli, ["-f", test_config_path, "evaluate", "-a"])
@@ -666,6 +723,12 @@ def test_generate_dataset_db_with_connection_string(
         print(result.output)
         assert result.exit_code == 0
 
+        with open(tmp_file, "r") as dataset_yml:
+            # Helps assert that the file was output correctly, namely, fides_keys were serialized as strings
+            # and not a FidesKey python object
+            dataset = yaml.safe_load(dataset_yml).get("dataset", [])
+            assert isinstance(dataset[0]["fides_key"], str)
+
     @pytest.mark.integration
     def test_generate_dataset_db_with_credentials_id(
         self,
diff --git a/tests/ctl/data/dataset_missing_categories.yml b/tests/ctl/data/dataset_missing_categories.yml
new file mode 100644
index 00000000000..51aab93782f
--- /dev/null
+++ b/tests/ctl/data/dataset_missing_categories.yml
@@ -0,0 +1,13 @@
+dataset:
+- collections:
+  - description: Organization information
+    fields:
+    - name: city
+    - data_categories:
+      - account.contact.state
+      name: state
+    name: organization
+  description: Sample dataset to be annotated
+  fides_key: test_missing_data_categories
+  name: Sample Dataset
+  organization_fides_key: default_organization