diff --git a/client/src/components/WorkflowInvocationState/InvocationMessage.vue b/client/src/components/WorkflowInvocationState/InvocationMessage.vue
index d31a4189b0bd..840ad7ed44f3 100644
--- a/client/src/components/WorkflowInvocationState/InvocationMessage.vue
+++ b/client/src/components/WorkflowInvocationState/InvocationMessage.vue
@@ -62,7 +62,12 @@ const workflow = computed(() => {
 });
 
 const workflowStep = computed(() => {
-    if ("workflow_step_id" in props.invocationMessage && workflow.value) {
+    if (
+        "workflow_step_id" in props.invocationMessage &&
+        props.invocationMessage.workflow_step_id !== undefined &&
+        props.invocationMessage.workflow_step_id !== null &&
+        workflow.value
+    ) {
         return workflow.value.steps[props.invocationMessage.workflow_step_id];
     }
     return undefined;
@@ -146,10 +151,14 @@ const infoString = computed(() => {
             invocationMessage.workflow_step_id + 1
         } is a conditional step and the result of the when expression is not a boolean type.`;
     } else if (reason === "unexpected_failure") {
+        let atStep = "";
+        if (invocationMessage.workflow_step_id !== null && invocationMessage.workflow_step_id !== undefined) {
+            atStep = ` at step ${invocationMessage.workflow_step_id + 1}`;
+        }
         if (invocationMessage.details) {
-            return `${failFragment} an unexpected failure occurred: '${invocationMessage.details}'`;
+            return `${failFragment} an unexpected failure occurred${atStep}: '${invocationMessage.details}'`;
         }
-        return `${failFragment} an unexpected failure occurred.`;
+        return `${failFragment} an unexpected failure occurred${atStep}.`;
     } else if (reason === "workflow_output_not_found") {
         return `Defined workflow output '${invocationMessage.output_name}' was not found in step ${
             invocationMessage.workflow_step_id + 1
diff --git a/client/src/components/WorkflowInvocationState/invocationMessageModel.ts b/client/src/components/WorkflowInvocationState/invocationMessageModel.ts
index 7c86d43ad17c..29ab6a989847 100644
--- a/client/src/components/WorkflowInvocationState/invocationMessageModel.ts
+++ b/client/src/components/WorkflowInvocationState/invocationMessageModel.ts
@@ -77,7 +77,7 @@ export interface GenericInvocationFailureCollectionFailedEncodedDatabaseIdField
     /**
      * HistoryDatasetCollectionAssociation ID that relates to failure.
      */
-    hdca_id?: string;
+    hdca_id: string;
     /**
      * Workflow step id of step that caused failure.
      */
@@ -92,7 +92,7 @@ export interface GenericInvocationFailureCollectionFailedInt {
     /**
      * HistoryDatasetCollectionAssociation ID that relates to failure.
      */
-    hdca_id?: number;
+    hdca_id: number;
     /**
      * Workflow step id of step that caused failure.
      */
@@ -159,7 +159,7 @@ export interface GenericInvocationFailureJobFailedEncodedDatabaseIdField {
     /**
      * Job ID that relates to failure.
      */
-    job_id?: string;
+    job_id: string;
     /**
      * Workflow step id of step that caused failure.
      */
@@ -174,7 +174,7 @@ export interface GenericInvocationFailureJobFailedInt {
     /**
      * Job ID that relates to failure.
      */
-    job_id?: number;
+    job_id: number;
     /**
      * Workflow step id of step that caused failure.
      */
@@ -232,6 +232,10 @@ export interface GenericInvocationUnexpectedFailureEncodedDatabaseIdField {
      * May contains details to help troubleshoot this problem.
      */
     details?: string;
+    /**
+     * Workflow step id of step that failed.
+     */
+    workflow_step_id?: number;
 }
 export interface GenericInvocationUnexpectedFailureInt {
     reason: "unexpected_failure";
@@ -239,4 +243,8 @@ export interface GenericInvocationUnexpectedFailureInt {
      * May contains details to help troubleshoot this problem.
      */
     details?: string;
+    /**
+     * Workflow step id of step that failed.
+     */
+    workflow_step_id?: number;
 }
diff --git a/lib/galaxy/schema/invocation.py b/lib/galaxy/schema/invocation.py
index 0d2617a25862..fad8f6deba8c 100644
--- a/lib/galaxy/schema/invocation.py
+++ b/lib/galaxy/schema/invocation.py
@@ -51,7 +51,10 @@ def get(self, key: Any, default: Any = None) -> Any:
         # Fetch the order_index when serializing for the API,
         # which makes much more sense when pointing to steps.
         if key == "workflow_step_id":
-            return self._obj.workflow_step.order_index
+            if self._obj.workflow_step:
+                return self._obj.workflow_step.order_index
+            else:
+                return default
         elif key == "dependent_workflow_step_id":
             if self._obj.dependent_workflow_step_id:
                 return self._obj.dependent_workflow_step.order_index
@@ -132,6 +135,7 @@ class GenericInvocationFailureWhenNotBoolean(InvocationFailureMessageBase[Databa
 class GenericInvocationUnexpectedFailure(InvocationMessageBase, Generic[DatabaseIdT]):
     reason: Literal[FailureReason.unexpected_failure]
     details: Optional[str] = Field(None, description="May contains details to help troubleshoot this problem.")
+    workflow_step_id: Optional[int] = Field(None, description="Workflow step id of step that failed.")
 
 
 class GenericInvocationWarning(InvocationMessageBase, Generic[DatabaseIdT]):
diff --git a/lib/galaxy/tools/__init__.py b/lib/galaxy/tools/__init__.py
index 62bf8b5e217b..3d5838d96490 100644
--- a/lib/galaxy/tools/__init__.py
+++ b/lib/galaxy/tools/__init__.py
@@ -2861,7 +2861,7 @@ def exec_after_process(self, app, inp_data, out_data, param_dict, job=None, **kw
                         copy_object = input_dataset
                         break
                 if copy_object is None:
-                    raise Exception("Failed to find dataset output.")
+                    raise exceptions.MessageException("Failed to find dataset output.")
                 out_data[key].copy_from(copy_object)
 
     def parse_environment_variables(self, tool_source):
@@ -3335,7 +3335,7 @@ def produce_outputs(self, trans, out_data, output_collections, incoming, history
         elif how == "by_index":
             extracted_element = collection[int(incoming["which"]["index"])]
         else:
-            raise Exception("Invalid tool parameters.")
+            raise exceptions.MessageException("Invalid tool parameters.")
         extracted = extracted_element.element_object
         extracted_o = extracted.copy(
             copy_tags=extracted.tags, new_name=extracted_element.element_identifier, flush=False
@@ -3375,7 +3375,9 @@ def produce_outputs(self, trans, out_data, output_collections, incoming, history
                 if element_identifier not in identifiers_map:
                     identifiers_map[element_identifier] = []
                 elif dupl_actions == "fail":
-                    raise Exception(f"Duplicate collection element identifiers found for [{element_identifier}]")
+                    raise exceptions.MessageException(
+                        f"Duplicate collection element identifiers found for [{element_identifier}]"
+                    )
                 identifiers_map[element_identifier].append(input_num)
 
         for copy, input_list in enumerate(input_lists):
@@ -3567,12 +3569,12 @@ def produce_outputs(self, trans, out_data, output_collections, incoming, history
                 except KeyError:
                     hdca_history_name = f"{hdca.hid}: {hdca.name}"
                     message = f"List of element identifiers does not match element identifiers in collection '{hdca_history_name}'"
-                    raise Exception(message)
+                    raise exceptions.MessageException(message)
             else:
                 message = f"Number of lines must match number of list elements ({len(elements)}), but file has {data_lines} lines"
-                raise Exception(message)
+                raise exceptions.MessageException(message)
         else:
-            raise Exception(f"Unknown sort_type '{sorttype}'")
+            raise exceptions.MessageException(f"Unknown sort_type '{sorttype}'")
 
         if presort_elements is not None:
             sorted_elements = [x[1] for x in sorted(presort_elements, key=lambda x: x[0])]
@@ -3604,7 +3606,7 @@ def produce_outputs(self, trans, out_data, output_collections, incoming, history
         def add_copied_value_to_new_elements(new_label, dce_object):
             new_label = new_label.strip()
             if new_label in new_elements:
-                raise Exception(
+                raise exceptions.MessageException(
                     f"New identifier [{new_label}] appears twice in resulting collection, these values must be unique."
                 )
             if getattr(dce_object, "history_content_type", None) == "dataset":
@@ -3617,7 +3619,7 @@ def add_copied_value_to_new_elements(new_label, dce_object):
         with open(new_labels_path) as fh:
             new_labels = fh.readlines(1024 * 1000000)
         if strict and len(hdca.collection.elements) != len(new_labels):
-            raise Exception("Relabel mapping file contains incorrect number of identifiers")
+            raise exceptions.MessageException("Relabel mapping file contains incorrect number of identifiers")
         if how_type == "tabular":
             # We have a tabular file, where the first column is an existing element identifier,
             # and the second column is the new element identifier.
@@ -3629,7 +3631,7 @@ def add_copied_value_to_new_elements(new_label, dce_object):
                 default = None if strict else element_identifier
                 new_label = new_labels_dict.get(element_identifier, default)
                 if not new_label:
-                    raise Exception(f"Failed to find new label for identifier [{element_identifier}]")
+                    raise exceptions.MessageException(f"Failed to find new label for identifier [{element_identifier}]")
                 add_copied_value_to_new_elements(new_label, dce_object)
         else:
             # If new_labels_dataset_assoc is not a two-column tabular dataset we label with the current line of the dataset
@@ -3638,7 +3640,7 @@ def add_copied_value_to_new_elements(new_label, dce_object):
                 add_copied_value_to_new_elements(new_labels[i], dce_object)
         for key in new_elements.keys():
             if not re.match(r"^[\w\- \.,]+$", key):
-                raise Exception(f"Invalid new collection identifier [{key}]")
+                raise exceptions.MessageException(f"Invalid new collection identifier [{key}]")
         self._add_datasets_to_history(history, new_elements.values())
         output_collections.create_collection(
             next(iter(self.outputs.values())), "output", elements=new_elements, propagate_hda_tags=False
diff --git a/lib/galaxy/workflow/run.py b/lib/galaxy/workflow/run.py
index 6ddc56427672..d69fe79b6aa2 100644
--- a/lib/galaxy/workflow/run.py
+++ b/lib/galaxy/workflow/run.py
@@ -240,12 +240,20 @@ def invoke(self) -> Dict[int, Any]:
             except modules.DelayedWorkflowEvaluation as de:
                 step_delayed = delayed_steps = True
                 self.progress.mark_step_outputs_delayed(step, why=de.why)
-            except Exception:
+            except Exception as e:
                 log.exception(
                     "Failed to schedule %s, problem occurred on %s.",
                     self.workflow_invocation.workflow.log_str(),
                     step.log_str(),
                 )
+                if isinstance(e, MessageException):
+                    # This is the highest level at which we can inject the step id
+                    # to provide some more context to the exception.
+                    raise modules.FailWorkflowEvaluation(
+                        why=InvocationUnexpectedFailure(
+                            reason=FailureReason.unexpected_failure, details=str(e), workflow_step_id=step.id
+                        )
+                    )
                 raise
 
             if not step_delayed: