diff --git a/devtools/conda-envs/no_openeye.yaml b/devtools/conda-envs/no_openeye.yaml
index 1a4901e0..7db723d1 100644
--- a/devtools/conda-envs/no_openeye.yaml
+++ b/devtools/conda-envs/no_openeye.yaml
@@ -22,7 +22,7 @@ dependencies:
   - rdkit >=22
   - ambertools >=22
   - openff-utilities
-  - openff-toolkit-base >=0.11,<0.14
+  - openff-toolkit-base >=0.11
   - openff-forcefields
   - openff-interchange
   - openff-qcsubmit
@@ -33,7 +33,7 @@ dependencies:
   - importlib_metadata >=4
 
     # Optional
-  - forcebalance
+  - forcebalance >=1.9.6
   - openff-fragmenter-base
   - xtb-python
 
diff --git a/devtools/conda-envs/test-env.yaml b/devtools/conda-envs/test-env.yaml
index d92a1ad1..094311c6 100644
--- a/devtools/conda-envs/test-env.yaml
+++ b/devtools/conda-envs/test-env.yaml
@@ -22,7 +22,7 @@ dependencies:
   - click-option-group
   - rdkit
   - openff-utilities
-  - openff-toolkit-base >=0.11,<0.14
+  - openff-toolkit-base >=0.11
   - openff-forcefields
   - openff-interchange
   - openff-units
@@ -34,7 +34,7 @@ dependencies:
   - importlib_metadata >=4
 
     # Optional
-  - forcebalance
+  - forcebalance >=1.9.6
   - openff-fragmenter-base
   - xtb-python
   - openeye-toolkits
diff --git a/docs/releasehistory.md b/docs/releasehistory.md
index e1fd52a7..0082f143 100644
--- a/docs/releasehistory.md
+++ b/docs/releasehistory.md
@@ -9,6 +9,10 @@ Releases follow the ``major.minor.micro`` scheme recommended by
 
 <!-- ## Since last release -->
 
+### Bug Fixes
+* [#286] - Update for behavior/API changes in ForceBalance 1.9.6 and OFF Tookit 0.14.4.
+
+
 <!-- ## Version / Date DD-MM-YYYY -->
 
 ## 0.2.2 / 08-05-2023
diff --git a/openff/bespokefit/executor/services/fragmenter/app.py b/openff/bespokefit/executor/services/fragmenter/app.py
index f37d3338..114bdf6a 100644
--- a/openff/bespokefit/executor/services/fragmenter/app.py
+++ b/openff/bespokefit/executor/services/fragmenter/app.py
@@ -3,6 +3,7 @@
 from fastapi import APIRouter
 from fastapi.responses import Response
 from openff.fragmenter.fragment import FragmentationResult
+from openff.utilities import MissingOptionalDependencyError
 
 from openff.bespokefit.executor.services import current_settings
 from openff.bespokefit.executor.services.fragmenter import worker
@@ -95,7 +96,7 @@ def get_fragment_image(fragmentation_id: str, fragment_id: int) -> Response:
             image_width=200,
             image_height=200,
         )
-    except ModuleNotFoundError:
+    except (ModuleNotFoundError, MissingOptionalDependencyError):
         from openff.fragmenter.depiction import _rd_render_fragment
 
         svg_content = _rd_render_fragment(
diff --git a/openff/bespokefit/tests/conftest.py b/openff/bespokefit/tests/conftest.py
index bbe624ff..6cf62fbe 100644
--- a/openff/bespokefit/tests/conftest.py
+++ b/openff/bespokefit/tests/conftest.py
@@ -87,12 +87,10 @@ def clear_force_balance_caches():
         OE_TOOLKIT_CACHE_molecule_conformers,
         RDK_TOOLKIT_CACHE_find_smarts_matches,
         RDK_TOOLKIT_CACHE_molecule_conformers,
-        TOOLKIT_CACHE_ChemicalEnvironment_validate,
     )
 
     OE_TOOLKIT_CACHE_find_smarts_matches.clear()
     RDK_TOOLKIT_CACHE_find_smarts_matches.clear()
-    TOOLKIT_CACHE_ChemicalEnvironment_validate.clear()
     OE_TOOLKIT_CACHE_assign_partial_charges.clear()
     AT_TOOLKIT_CACHE_assign_partial_charges.clear()
     OE_TOOLKIT_CACHE_molecule_conformers.clear()