diff --git a/cumulusci/core/config/project_config.py b/cumulusci/core/config/project_config.py
index 856bca6401..72c3850e49 100644
--- a/cumulusci/core/config/project_config.py
+++ b/cumulusci/core/config/project_config.py
@@ -22,7 +22,7 @@
 API_VERSION_RE = re.compile(r"^\d\d+\.0$")
 
 import github3
-from pydantic import ValidationError
+from pydantic.v1 import ValidationError
 
 from cumulusci.core.config import FlowConfig, TaskConfig
 from cumulusci.core.config.base_task_flow_config import BaseTaskFlowConfig
diff --git a/cumulusci/core/dependencies/dependencies.py b/cumulusci/core/dependencies/dependencies.py
index 3301cdb8a5..2c0050dcba 100644
--- a/cumulusci/core/dependencies/dependencies.py
+++ b/cumulusci/core/dependencies/dependencies.py
@@ -6,10 +6,10 @@
 from typing import List, Optional
 from zipfile import ZipFile
 
-import pydantic
+import pydantic.v1 as pydantic
 from github3.exceptions import NotFoundError
 from github3.repos.repo import Repository
-from pydantic.networks import AnyUrl
+from pydantic.v1.networks import AnyUrl
 
 from cumulusci.core.config import OrgConfig
 from cumulusci.core.config.project_config import BaseProjectConfig
diff --git a/cumulusci/core/dependencies/tests/test_dependencies.py b/cumulusci/core/dependencies/tests/test_dependencies.py
index e0c757c7aa..dc57210c0c 100644
--- a/cumulusci/core/dependencies/tests/test_dependencies.py
+++ b/cumulusci/core/dependencies/tests/test_dependencies.py
@@ -5,7 +5,7 @@
 from zipfile import ZipFile
 
 import pytest
-from pydantic import ValidationError
+from pydantic.v1 import ValidationError
 
 from cumulusci.core.config.org_config import OrgConfig, VersionInfo
 from cumulusci.core.config.project_config import BaseProjectConfig
diff --git a/cumulusci/core/source_transforms/tests/test_transforms.py b/cumulusci/core/source_transforms/tests/test_transforms.py
index 99230f2fe2..619e9a125e 100644
--- a/cumulusci/core/source_transforms/tests/test_transforms.py
+++ b/cumulusci/core/source_transforms/tests/test_transforms.py
@@ -8,7 +8,7 @@
 
 import pytest
 from lxml import etree as ET
-from pydantic import ValidationError
+from pydantic.v1 import ValidationError
 
 from cumulusci.core.exceptions import CumulusCIException, TaskOptionsError
 from cumulusci.core.source_transforms.transforms import (
diff --git a/cumulusci/core/source_transforms/transforms.py b/cumulusci/core/source_transforms/transforms.py
index ab311b1456..9bf0499a8e 100644
--- a/cumulusci/core/source_transforms/transforms.py
+++ b/cumulusci/core/source_transforms/transforms.py
@@ -10,7 +10,7 @@
 from zipfile import ZipFile
 
 from lxml import etree as ET
-from pydantic import BaseModel, root_validator
+from pydantic.v1 import BaseModel, root_validator
 
 from cumulusci.core.dependencies.utils import TaskContext
 from cumulusci.core.enums import StrEnum
diff --git a/cumulusci/core/tasks.py b/cumulusci/core/tasks.py
index 0d8269aea4..7c8cffc2fb 100644
--- a/cumulusci/core/tasks.py
+++ b/cumulusci/core/tasks.py
@@ -11,7 +11,7 @@
 from contextlib import nullcontext
 from typing import Any, Callable, Dict, List, Optional, Type, Union
 
-from pydantic.error_wrappers import ValidationError
+from pydantic.v1.error_wrappers import ValidationError
 
 from cumulusci import __version__
 from cumulusci.core.config import TaskConfig
diff --git a/cumulusci/core/versions.py b/cumulusci/core/versions.py
index 21b34ff1e3..21437847d2 100644
--- a/cumulusci/core/versions.py
+++ b/cumulusci/core/versions.py
@@ -1,7 +1,7 @@
 import re
 from typing import Optional, Union
 
-from pydantic import BaseModel
+from pydantic.v1 import BaseModel
 
 from cumulusci.core.enums import StrEnum
 
diff --git a/cumulusci/oauth/client.py b/cumulusci/oauth/client.py
index 9d812c7def..91059eba15 100644
--- a/cumulusci/oauth/client.py
+++ b/cumulusci/oauth/client.py
@@ -19,7 +19,7 @@
 from cryptography.hazmat.primitives import hashes, serialization
 from cryptography.hazmat.primitives.asymmetric import rsa
 from cryptography.x509.oid import NameOID
-from pydantic import BaseModel
+from pydantic.v1 import BaseModel
 
 from cumulusci.core.exceptions import CumulusCIUsageError
 from cumulusci.oauth.exceptions import OAuth2Error
diff --git a/cumulusci/tasks/bulkdata/extract_dataset_utils/extract_yml.py b/cumulusci/tasks/bulkdata/extract_dataset_utils/extract_yml.py
index cec42d0bd9..1ece5c1cd7 100644
--- a/cumulusci/tasks/bulkdata/extract_dataset_utils/extract_yml.py
+++ b/cumulusci/tasks/bulkdata/extract_dataset_utils/extract_yml.py
@@ -2,7 +2,7 @@
 import typing as T
 from pathlib import Path
 
-from pydantic import Field, validator
+from pydantic.v1 import Field, validator
 
 from cumulusci.core.enums import StrEnum
 from cumulusci.tasks.bulkdata.utils import DataApi
diff --git a/cumulusci/tasks/bulkdata/extract_dataset_utils/synthesize_extract_declarations.py b/cumulusci/tasks/bulkdata/extract_dataset_utils/synthesize_extract_declarations.py
index bfec28ef54..49febd966d 100644
--- a/cumulusci/tasks/bulkdata/extract_dataset_utils/synthesize_extract_declarations.py
+++ b/cumulusci/tasks/bulkdata/extract_dataset_utils/synthesize_extract_declarations.py
@@ -2,7 +2,7 @@
 import re
 import typing as T
 
-from pydantic import validator
+from pydantic.v1 import validator
 
 from cumulusci.salesforce_api.org_schema import NOT_EXTRACTABLE, Field, Schema
 from cumulusci.utils.iterators import partition
diff --git a/cumulusci/tasks/bulkdata/extract_dataset_utils/tests/test_extract_yml.py b/cumulusci/tasks/bulkdata/extract_dataset_utils/tests/test_extract_yml.py
index 8daf124e25..127b40b172 100644
--- a/cumulusci/tasks/bulkdata/extract_dataset_utils/tests/test_extract_yml.py
+++ b/cumulusci/tasks/bulkdata/extract_dataset_utils/tests/test_extract_yml.py
@@ -1,7 +1,7 @@
 from io import StringIO
 
 import pytest
-from pydantic import ValidationError
+from pydantic.v1 import ValidationError
 
 from cumulusci.tasks.bulkdata.extract_dataset_utils.extract_yml import (
     ExtractDeclaration,
diff --git a/cumulusci/tasks/bulkdata/mapping_parser.py b/cumulusci/tasks/bulkdata/mapping_parser.py
index 28b71b1f34..cad6451345 100644
--- a/cumulusci/tasks/bulkdata/mapping_parser.py
+++ b/cumulusci/tasks/bulkdata/mapping_parser.py
@@ -7,7 +7,7 @@
 from pathlib import Path
 from typing import IO, Any, Callable, Dict, List, Mapping, Optional, Tuple, Union
 
-from pydantic import Field, ValidationError, root_validator, validator
+from pydantic.v1 import Field, ValidationError, root_validator, validator
 from simple_salesforce import Salesforce
 from typing_extensions import Literal
 
diff --git a/cumulusci/tasks/bulkdata/select_utils.py b/cumulusci/tasks/bulkdata/select_utils.py
index 7835d8dea8..81c3c0e2d9 100644
--- a/cumulusci/tasks/bulkdata/select_utils.py
+++ b/cumulusci/tasks/bulkdata/select_utils.py
@@ -4,7 +4,7 @@
 import typing as T
 from enum import Enum
 
-from pydantic import Field, root_validator, validator
+from pydantic.v1 import Field, root_validator, validator
 
 from cumulusci.core.enums import StrEnum
 from cumulusci.tasks.bulkdata.utils import CaseInsensitiveDict
diff --git a/cumulusci/tasks/create_package_version.py b/cumulusci/tasks/create_package_version.py
index 14a80334fc..9933b3e49e 100644
--- a/cumulusci/tasks/create_package_version.py
+++ b/cumulusci/tasks/create_package_version.py
@@ -5,7 +5,7 @@
 import zipfile
 from typing import List, Optional
 
-from pydantic import BaseModel, validator
+from pydantic.v1 import BaseModel, validator
 from simple_salesforce.exceptions import SalesforceMalformedRequest
 
 from cumulusci.core.config.util import get_devhub_config
diff --git a/cumulusci/tasks/datadictionary.py b/cumulusci/tasks/datadictionary.py
index 4a8773260c..04418512ce 100644
--- a/cumulusci/tasks/datadictionary.py
+++ b/cumulusci/tasks/datadictionary.py
@@ -6,7 +6,7 @@
 from zipfile import ZipFile
 
 from github3.repos.repo import Repository
-from pydantic import BaseModel
+from pydantic.v1 import BaseModel
 
 from cumulusci.core.dependencies.dependencies import (
     Dependency,
diff --git a/cumulusci/tasks/metadata_etl/layouts.py b/cumulusci/tasks/metadata_etl/layouts.py
index 4b6ed9fbe6..425c53de85 100644
--- a/cumulusci/tasks/metadata_etl/layouts.py
+++ b/cumulusci/tasks/metadata_etl/layouts.py
@@ -1,6 +1,6 @@
 from typing import List, Optional
 
-from pydantic import BaseModel, root_validator
+from pydantic.v1 import BaseModel, root_validator
 from typing_extensions import Literal
 
 from cumulusci.core.exceptions import TaskOptionsError
diff --git a/cumulusci/tasks/metadata_etl/permissions.py b/cumulusci/tasks/metadata_etl/permissions.py
index 9a453e14f3..6d2baedb79 100644
--- a/cumulusci/tasks/metadata_etl/permissions.py
+++ b/cumulusci/tasks/metadata_etl/permissions.py
@@ -1,6 +1,6 @@
 import typing as T
 
-import pydantic
+import pydantic.v1 as pydantic
 
 from cumulusci.core.exceptions import TaskOptionsError
 from cumulusci.tasks.metadata_etl import MetadataSingleEntityTransformTask
diff --git a/cumulusci/tasks/metadata_etl/remote_site_settings.py b/cumulusci/tasks/metadata_etl/remote_site_settings.py
index 7add3b6e3d..907d5143d1 100644
--- a/cumulusci/tasks/metadata_etl/remote_site_settings.py
+++ b/cumulusci/tasks/metadata_etl/remote_site_settings.py
@@ -1,7 +1,7 @@
 from typing import List, Optional
 
-import pydantic
-from pydantic import BaseModel
+import pydantic.v1 as pydantic
+from pydantic.v1 import BaseModel
 
 from cumulusci.core.exceptions import TaskOptionsError
 from cumulusci.tasks.metadata_etl.base import BaseMetadataSynthesisTask
diff --git a/cumulusci/tasks/salesforce/Deploy.py b/cumulusci/tasks/salesforce/Deploy.py
index 66a5851b80..8c6ff6350c 100644
--- a/cumulusci/tasks/salesforce/Deploy.py
+++ b/cumulusci/tasks/salesforce/Deploy.py
@@ -2,7 +2,7 @@
 from typing import List, Optional, Union
 
 from defusedxml.minidom import parseString
-from pydantic import ValidationError
+from pydantic.v1 import ValidationError
 
 from cumulusci.cli.ui import CliTable
 from cumulusci.core.dependencies.utils import TaskContext
diff --git a/cumulusci/tasks/salesforce/tests/test_update_dependencies.py b/cumulusci/tasks/salesforce/tests/test_update_dependencies.py
index 92e133c01e..266a24c7da 100644
--- a/cumulusci/tasks/salesforce/tests/test_update_dependencies.py
+++ b/cumulusci/tasks/salesforce/tests/test_update_dependencies.py
@@ -3,7 +3,7 @@
 import zipfile
 from unittest import mock
 
-import pydantic
+import pydantic.v1 as pydantic
 import pytest
 
 from cumulusci.core.dependencies.dependencies import (
diff --git a/cumulusci/tasks/tests/test_create_package_version.py b/cumulusci/tasks/tests/test_create_package_version.py
index e972529db8..c1983466fb 100644
--- a/cumulusci/tasks/tests/test_create_package_version.py
+++ b/cumulusci/tasks/tests/test_create_package_version.py
@@ -10,7 +10,7 @@
 import pytest
 import responses
 import yaml
-from pydantic import ValidationError
+from pydantic.v1 import ValidationError
 
 from cumulusci.core.config import BaseProjectConfig, TaskConfig, UniversalConfig
 from cumulusci.core.dependencies.dependencies import (
diff --git a/cumulusci/utils/options.py b/cumulusci/utils/options.py
index 5d5d2828f0..1dcf353145 100644
--- a/cumulusci/utils/options.py
+++ b/cumulusci/utils/options.py
@@ -2,7 +2,7 @@
 from inspect import signature
 from typing import Any, Dict, List
 
-from pydantic import DirectoryPath, Field, FilePath, create_model
+from pydantic.v1 import DirectoryPath, Field, FilePath, create_model
 
 from cumulusci.core.exceptions import TaskOptionsError
 from cumulusci.utils.yaml.model_parser import CCIDictModel
diff --git a/cumulusci/utils/parallel/task_worker_queues/parallel_worker.py b/cumulusci/utils/parallel/task_worker_queues/parallel_worker.py
index 72c3b84ad0..8130c37306 100644
--- a/cumulusci/utils/parallel/task_worker_queues/parallel_worker.py
+++ b/cumulusci/utils/parallel/task_worker_queues/parallel_worker.py
@@ -7,7 +7,7 @@
 from pathlib import Path
 from traceback import format_exc
 
-from pydantic import BaseModel
+from pydantic.v1 import BaseModel
 
 from cumulusci.core.config import (
     BaseConfig,
diff --git a/cumulusci/utils/yaml/cumulusci_yml.py b/cumulusci/utils/yaml/cumulusci_yml.py
index 93516ed654..78cc9ac960 100644
--- a/cumulusci/utils/yaml/cumulusci_yml.py
+++ b/cumulusci/utils/yaml/cumulusci_yml.py
@@ -9,8 +9,8 @@
 from pathlib import Path
 from typing import Any, Dict, List, Optional, Sequence, Union
 
-from pydantic import Field, root_validator, validator
-from pydantic.types import DirectoryPath
+from pydantic.v1 import Field, root_validator, validator
+from pydantic.v1.types import DirectoryPath
 from typing_extensions import Literal, TypedDict
 
 from cumulusci.core.enums import StrEnum
@@ -280,7 +280,6 @@ class ErrorDict(TypedDict):
 
 def _log_yaml_errors(logger, errors: List[ErrorDict]):
     "Format and log a Pydantic-style error dictionary"
-    global has_shown_yaml_error_message
     plural = "" if len(errors) <= 1 else "s"
     logger.warning(f"CumulusCI Configuration Warning{plural}:")
     for error in errors:
diff --git a/cumulusci/utils/yaml/model_parser.py b/cumulusci/utils/yaml/model_parser.py
index 249d914fbd..9d8434db56 100644
--- a/cumulusci/utils/yaml/model_parser.py
+++ b/cumulusci/utils/yaml/model_parser.py
@@ -1,8 +1,8 @@
 from pathlib import Path
 from typing import IO, Sequence, Union
 
-from pydantic import BaseModel, ValidationError
-from pydantic.error_wrappers import ErrorWrapper
+from pydantic.v1 import BaseModel, ValidationError
+from pydantic.v1.error_wrappers import ErrorWrapper
 
 from cumulusci.utils.yaml.safer_loader import load_from_source, load_yaml_data
 
diff --git a/cumulusci/utils/yaml/tests/test_cumulusci_yml.py b/cumulusci/utils/yaml/tests/test_cumulusci_yml.py
index dce7cb3af9..e8608af3f1 100644
--- a/cumulusci/utils/yaml/tests/test_cumulusci_yml.py
+++ b/cumulusci/utils/yaml/tests/test_cumulusci_yml.py
@@ -4,7 +4,7 @@
 from unittest.mock import MagicMock, Mock, patch
 
 import pytest
-from pydantic import ValidationError
+from pydantic.v1 import ValidationError
 
 from cumulusci.utils import temporary_dir
 from cumulusci.utils.yaml.cumulusci_yml import (
diff --git a/cumulusci/utils/yaml/tests/test_model_parser.py b/cumulusci/utils/yaml/tests/test_model_parser.py
index 5c2f9167e4..fcceca7159 100644
--- a/cumulusci/utils/yaml/tests/test_model_parser.py
+++ b/cumulusci/utils/yaml/tests/test_model_parser.py
@@ -2,7 +2,7 @@
 from unittest.mock import Mock
 
 import pytest
-from pydantic import Field
+from pydantic.v1 import Field
 
 from cumulusci.utils.yaml.model_parser import CCIDictModel, CCIModel, ValidationError
 
@@ -20,7 +20,7 @@ class TestCCIModel:
     def test_fields_property(self):
         # JSON is YAML. Strange but true.
         foo = Document.parse_from_yaml(StringIO("{bar: 'blah'}"))
-        assert type(foo) == Foo
+        assert isinstance(foo, Foo)
         assert foo.fields_ == []
         assert foo.fields == []
 
@@ -122,7 +122,7 @@ class Document(CCIDictModel):
 
         # JSON is YAML. Strange but true.
         foo = Document.parse_from_yaml(StringIO("{bar: 'blah'}"))
-        assert type(foo) == Foo
+        assert isinstance(foo, Foo)
         assert foo["fields"] == []
 
         foo = Document.parse_from_yaml(StringIO("{bar: 'blah', fields: [1,2]}"))
diff --git a/pyproject.toml b/pyproject.toml
index 14ee39ce02..66cdbf7053 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -36,7 +36,7 @@ dependencies = [
     "MarkupSafe",
     "packaging>=23.0",
     "psutil",
-    "pydantic<2",
+    "pydantic>=2.0,<3",
     "PyJWT",
     "pytz",
     "pyyaml",
@@ -53,7 +53,7 @@ dependencies = [
     "sarge",
     "selenium<4",
     "simple-salesforce==1.11.4",
-    "snowfakery>=4.0.0",
+    "snowfakery>=4.1.0",
     "xmltodict",
     "docutils<=0.21.2",
 ]
@@ -105,6 +105,9 @@ Changelog = "https://cumulusci.readthedocs.io/en/stable/history.html"
 [tool.hatch.version]
 path = "cumulusci/__about__.py"
 
+[tool.hatch.metadata]
+allow-direct-references = true
+
 [tool.hatch.build]
 include = [
     "/cumulusci",
diff --git a/uv.lock b/uv.lock
index efb1f015cb..071af4e7ba 100644
--- a/uv.lock
+++ b/uv.lock
@@ -29,6 +29,15 @@ wheels = [
     { url = "https://files.pythonhosted.org/packages/7e/b3/6b4067be973ae96ba0d615946e314c5ae35f9f993eca561b356540bb0c2b/alabaster-1.0.0-py3-none-any.whl", hash = "sha256:fc6786402dc3fcb2de3cabd5fe455a2db534b371124f1f21de8731783dec828b", size = 13929, upload-time = "2024-07-26T18:15:02.05Z" },
 ]
 
+[[package]]
+name = "annotated-types"
+version = "0.7.0"
+source = { registry = "https://pypi.org/simple" }
+sdist = { url = "https://files.pythonhosted.org/packages/ee/67/531ea369ba64dcff5ec9c3402f9f51bf748cec26dde048a2f973a4eea7f5/annotated_types-0.7.0.tar.gz", hash = "sha256:aff07c09a53a08bc8cfccb9c85b05f1aa9a2a6f23728d790723543408344ce89", size = 16081, upload-time = "2024-05-20T21:33:25.928Z" }
+wheels = [
+    { url = "https://files.pythonhosted.org/packages/78/b6/6307fbef88d9b5ee7421e68d78a9f162e0da4900bc5f5793f6d3d0e34fb8/annotated_types-0.7.0-py3-none-any.whl", hash = "sha256:1f02e8b43a8fbbc3f3e0d4f0f4bfc8131bcb4eebe8849b8e5c773f3a1c582a53", size = 13643, upload-time = "2024-05-20T21:33:24.1Z" },
+]
+
 [[package]]
 name = "annoy"
 version = "1.17.3"
@@ -401,6 +410,7 @@ dependencies = [
     { name = "keyring" },
     { name = "lxml" },
     { name = "markupsafe" },
+    { name = "packaging" },
     { name = "psutil" },
     { name = "pydantic" },
     { name = "pyjwt" },
@@ -474,9 +484,10 @@ requires-dist = [
     { name = "lxml" },
     { name = "markupsafe" },
     { name = "numpy", marker = "extra == 'select'" },
+    { name = "packaging", specifier = ">=23.0" },
     { name = "pandas", marker = "extra == 'select'" },
     { name = "psutil" },
-    { name = "pydantic", specifier = "<2" },
+    { name = "pydantic", specifier = ">=2.0,<3" },
     { name = "pyjwt" },
     { name = "python-dateutil" },
     { name = "pytz" },
@@ -494,7 +505,7 @@ requires-dist = [
     { name = "scikit-learn", marker = "extra == 'select'" },
     { name = "selenium", specifier = "<4" },
     { name = "simple-salesforce", specifier = "==1.11.4" },
-    { name = "snowfakery", specifier = ">=4.0.0" },
+    { name = "snowfakery", specifier = ">=4.1.0" },
     { name = "sqlalchemy", specifier = "<2" },
     { name = "xmltodict" },
 ]
@@ -1401,35 +1412,82 @@ wheels = [
 
 [[package]]
 name = "pydantic"
-version = "1.10.22"
+version = "2.11.9"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
+    { name = "annotated-types" },
+    { name = "pydantic-core" },
     { name = "typing-extensions" },
+    { name = "typing-inspection" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/9a/57/5996c63f0deec09e9e901a2b838247c97c6844999562eac4e435bcb83938/pydantic-1.10.22.tar.gz", hash = "sha256:ee1006cebd43a8e7158fb7190bb8f4e2da9649719bff65d0c287282ec38dec6d", size = 356771, upload-time = "2025-04-24T13:38:43.605Z" }
-wheels = [
-    { url = "https://files.pythonhosted.org/packages/42/03/e435ed85a9abda29e3fbdb49c572fe4131a68c6daf3855a01eebda9e1b27/pydantic-1.10.22-cp311-cp311-macosx_10_9_x86_64.whl", hash = "sha256:8e530a8da353f791ad89e701c35787418605d35085f4bdda51b416946070e938", size = 2845682, upload-time = "2025-04-24T13:37:10.142Z" },
-    { url = "https://files.pythonhosted.org/packages/72/ea/4a625035672f6c06d3f1c7e33aa0af6bf1929991e27017e98b9c2064ae0b/pydantic-1.10.22-cp311-cp311-macosx_11_0_arm64.whl", hash = "sha256:654322b85642e9439d7de4c83cb4084ddd513df7ff8706005dada43b34544946", size = 2553286, upload-time = "2025-04-24T13:37:11.946Z" },
-    { url = "https://files.pythonhosted.org/packages/a4/f0/424ad837746e69e9f061ba9be68c2a97aef7376d1911692904d8efbcd322/pydantic-1.10.22-cp311-cp311-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:a8bece75bd1b9fc1c32b57a32831517943b1159ba18b4ba32c0d431d76a120ae", size = 3141232, upload-time = "2025-04-24T13:37:14.394Z" },
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