diff --git a/planemo/galaxy/activity.py b/planemo/galaxy/activity.py
index 5e7578b44..2aac4f84f 100644
--- a/planemo/galaxy/activity.py
+++ b/planemo/galaxy/activity.py
@@ -20,6 +20,7 @@
 from galaxy.tools.parser import get_tool_source
 
 
+from planemo.galaxy.api import summarize_history
 from planemo.io import wait_on
 from planemo.runnable import (
     ErrorRunResponse,
@@ -41,25 +42,35 @@ def execute(ctx, config, runnable, job_path, **kwds):
         return ErrorRunResponse(str(e))
 
 
+def _verified_tool_id(runnable, user_gi):
+    tool_id = _tool_id(runnable.path)
+    try:
+        user_gi.tools.show_tool(tool_id)
+    except Exception as e:
+        raise Exception(ERR_NO_SUCH_TOOL % (tool_id, e))
+    return tool_id
+
+
+def _inputs_representation(runnable):
+    if runnable.type == RunnableType.cwl_tool:
+        inputs_representation = "cwl"
+    else:
+        inputs_representation = "galaxy"
+    return inputs_representation
+
+
 def _execute(ctx, config, runnable, job_path, **kwds):
     user_gi = config.user_gi
     admin_gi = config.gi
 
     history_id = _history_id(user_gi, **kwds)
 
-    galaxy_paths, job_dict, datasets = stage_in(ctx, runnable, config, user_gi, history_id, job_path, **kwds)
+    galaxy_paths, job_dict, _ = stage_in(ctx, runnable, config, user_gi, history_id, job_path, **kwds)
 
     if runnable.type in [RunnableType.galaxy_tool, RunnableType.cwl_tool]:
         response_class = GalaxyToolRunResponse
-        tool_id = _tool_id(runnable.path)
-        if runnable.type == RunnableType.cwl_tool:
-            inputs_representation = "cwl"
-        else:
-            inputs_representation = "galaxy"
-        try:
-            user_gi.tools.show_tool(tool_id)
-        except Exception as e:
-            raise Exception(ERR_NO_SUCH_TOOL % (tool_id, e))
+        tool_id = _verified_tool_id(runnable)
+        inputs_representation = _inputs_representation(runnable)
         run_tool_payload = dict(
             history_id=history_id,
             tool_id=tool_id,
@@ -71,9 +82,14 @@ def _execute(ctx, config, runnable, job_path, **kwds):
 
         job = tool_run_response["jobs"][0]
         job_id = job["id"]
-        final_state = _wait_for_job(user_gi, job_id)
+        try:
+            final_state = _wait_for_job(user_gi, job_id)
+        except Exception:
+            summarize_history(ctx, user_gi, history_id)
+            raise
         if final_state != "ok":
             msg = "Failed to run CWL tool job final job state is [%s]." % final_state
+            summarize_history(ctx, user_gi, history_id)
             with open("errored_galaxy.log", "w") as f:
                 f.write(config.log_contents)
             raise Exception(msg)
@@ -110,14 +126,16 @@ def _execute(ctx, config, runnable, job_path, **kwds):
         invocation_id = invocation["id"]
         ctx.vlog("Waiting for invocation [%s]" % invocation_id)
         try:
-            final_invocation_state = _wait_for_invocation(ctx, user_gi, workflow_id, invocation_id)
+            final_invocation_state = _wait_for_invocation(ctx, user_gi, history_id, workflow_id, invocation_id)
         except Exception:
             ctx.vlog("Problem waiting on invocation...")
+            summarize_history(ctx, user_gi, history_id)
             raise
         ctx.vlog("Final invocation state is [%s]" % final_invocation_state)
-        final_state = _wait_for_history(user_gi, history_id)
+        final_state = _wait_for_history(ctx, user_gi, history_id)
         if final_state != "ok":
             msg = "Failed to run workflow final history state is [%s]." % final_state
+            summarize_history(ctx, user_gi, history_id)
             with open("errored_galaxy.log", "w") as f:
                 f.write(config.log_contents)
             raise Exception(msg)
@@ -156,15 +174,17 @@ def upload_func(upload_target):
             )
             name = os.path.basename(file_path)
             upload_payload["inputs"]["files_0|auto_decompress"] = False
+            upload_payload["inputs"]["auto_decompress"] = False
             upload_payload["inputs"]["files_0|url_paste"] = "file://%s" % os.path.abspath(file_path)
             upload_payload["inputs"]["files_0|NAME"] = name
             if upload_target.secondary_files:
-                upload_payload["files_1|url_paste"] = "file://%s" % os.path.abspath(upload_target.secondary_files)
-                upload_payload["files_1|type"] = "upload_dataset"
-                upload_payload["files_1|auto_decompress"] = True
-                upload_payload["file_count"] = "2"
-                upload_payload["force_composite"] = "True"
+                upload_payload["inputs"]["files_1|url_paste"] = "file://%s" % os.path.abspath(upload_target.secondary_files)
+                upload_payload["inputs"]["files_1|type"] = "upload_dataset"
+                upload_payload["inputs"]["files_1|auto_decompress"] = True
+                upload_payload["inputs"]["file_count"] = "2"
+                upload_payload["inputs"]["force_composite"] = "True"
 
+            ctx.vlog("upload_payload is %s" % upload_payload)
             return user_gi.tools._tool_post(upload_payload, files_attached=False)
         elif isinstance(upload_target, DirectoryUploadTarget):
             tar_path = upload_target.tar_path
@@ -218,7 +238,7 @@ def create_collection_func(element_identifiers, collection_type):
     )
 
     if datasets:
-        final_state = _wait_for_history(user_gi, history_id)
+        final_state = _wait_for_history(ctx, user_gi, history_id)
 
         for (dataset, path) in datasets:
             dataset_details = user_gi.histories.show_dataset(
@@ -233,6 +253,7 @@ def create_collection_func(element_identifiers, collection_type):
     ctx.vlog("final state is %s" % final_state)
     if final_state != "ok":
         msg = "Failed to run CWL job final job state is [%s]." % final_state
+        summarize_history(ctx, user_gi, history_id)
         with open("errored_galaxy.log", "w") as f:
             f.write(config.log_contents)
         raise Exception(msg)
@@ -516,18 +537,25 @@ def _history_id(gi, **kwds):
     return history_id
 
 
-def _wait_for_invocation(ctx, gi, workflow_id, invocation_id):
+def _wait_for_invocation(ctx, gi, history_id, workflow_id, invocation_id):
 
     def state_func():
-        # TODO: Hack gi to work around Galaxy simply handing on this request
-        # sometimes.
-        gi.timeout = 60
-        rval = None
-        try_count = 5
+        if _retry_on_timeouts(ctx, gi, lambda gi: has_jobs_in_states(gi, history_id, ["error", "deleted", "deleted_new"])):
+            raise Exception("Problem running workflow, one or more jobs failed.")
+
+        return _retry_on_timeouts(ctx, gi, lambda gi: gi.workflows.show_invocation(workflow_id, invocation_id))
+
+    return _wait_on_state(state_func)
+
+
+def _retry_on_timeouts(ctx, gi, f):
+    gi.timeout = 60
+    try_count = 5
+    try:
         for try_num in range(try_count):
             start_time = time.time()
             try:
-                rval = gi.workflows.show_invocation(workflow_id, invocation_id)
+                return f(gi)
             except Exception:
                 end_time = time.time()
                 if end_time - start_time > 45 and (try_num + 1) < try_count:
@@ -535,30 +563,32 @@ def state_func():
                     continue
                 else:
                     raise
+    finally:
         gi.timeout = None
-        return rval
 
-    return _wait_on_state(state_func)
 
+def has_jobs_in_states(gi, history_id, states):
+    params = {"history_id": history_id}
+    jobs_url = gi._make_url(gi.jobs)
+    jobs = Client._get(gi.jobs, params=params, url=jobs_url)
+
+    target_jobs = [j for j in jobs if j["state"] in states]
 
-def _wait_for_history(gi, history_id):
+    return len(target_jobs) > 0
 
-    def has_active_jobs():
-        params = {"history_id": history_id}
-        jobs_url = gi._make_url(gi.jobs)
-        jobs = Client._get(gi.jobs, params=params, url=jobs_url)
 
-        active_jobs = [j for j in jobs if j["state"] in ["new", "upload", "waiting", "queued", "running"]]
+def _wait_for_history(ctx, gi, history_id):
 
-        if len(active_jobs) == 0:
+    def has_active_jobs(gi):
+        if has_jobs_in_states(gi, history_id, ["new", "upload", "waiting", "queued", "running"]):
             return True
         else:
             return None
 
-    wait_on(has_active_jobs, "active jobs", timeout=60 * 60 * 24)
+    wait_on(lambda: _retry_on_timeouts(ctx, gi, has_active_jobs), "active jobs", timeout=60 * 60 * 24)
 
     def state_func():
-        return gi.histories.show_history(history_id)
+        return _retry_on_timeouts(ctx, gi, lambda gi: gi.histories.show_history(history_id))
 
     return _wait_on_state(state_func)
 
diff --git a/planemo/galaxy/api.py b/planemo/galaxy/api.py
index e432bbfe7..97523e708 100644
--- a/planemo/galaxy/api.py
+++ b/planemo/galaxy/api.py
@@ -1,4 +1,6 @@
 """A high-level interface to local Galaxy instances using bioblend."""
+from six import StringIO
+
 from planemo.bioblend import ensure_module
 from planemo.bioblend import galaxy
 
@@ -47,6 +49,60 @@ def user_api_key(admin_gi):
     return users.create_user_apikey(user_id)
 
 
+def summarize_history(ctx, gi, history_id):
+    """Summarize a history with print() based on similar code in Galaxy for populators.
+    """
+    if not ctx.verbose:
+        return
+
+    if history_id is None:
+        raise ValueError("summarize_history passed empty history_id")
+    try:
+        history_contents = gi.histories.show_history(history_id, contents=True)
+    except Exception:
+        print("Failed to fetch history contents in summarize_history.")
+        return
+
+    for history_content in history_contents:
+        history_content_id = history_content.get('id', None)
+        print("| %d - %s (HID - NAME) " % (int(history_content['hid']), history_content['name']))
+        if history_content['history_content_type'] == 'dataset_collection':
+            history_contents_json = gi.histories.show_dataset_collection(history_id, history_content["id"])
+            print("| Dataset Collection: %s" % history_contents_json)
+            continue
+        try:
+            dataset_info = gi.histories.show_dataset(history_id, history_content_id)
+            print("| Dataset State:")
+            print(_format_for_summary(dataset_info.get("state"), "Dataset state is unknown."))
+            print("| Dataset Blurb:")
+            print(_format_for_summary(dataset_info.get("misc_blurb", ""), "Dataset blurb was empty."))
+            print("| Dataset Info:")
+            print(_format_for_summary(dataset_info.get("misc_info", ""), "Dataset info is empty."))
+            print("| Peek:")
+            print(_format_for_summary(dataset_info.get("peek", ""), "Peek unavilable."))
+        except Exception:
+            print("| *PLANEMO ERROR FETCHING DATASET DETAILS*")
+        try:
+            provenance_info = _dataset_provenance(gi, history_id, history_content_id)
+            print("| Dataset Job Standard Output:")
+            print(_format_for_summary(provenance_info.get("stdout", ""), "Standard output was empty."))
+            print("| Dataset Job Standard Error:")
+            print(_format_for_summary(provenance_info.get("stderr", ""), "Standard error was empty."))
+        except Exception:
+            print("| *PLANEMO ERROR FETCHING JOB DETAILS*")
+        print("|")
+
+
+def _format_for_summary(blob, empty_message, prefix="|  "):
+    contents = "\n".join(["%s%s" % (prefix, line.strip()) for line in StringIO(blob).readlines() if line.rstrip("\n\r")])
+    return contents or "%s*%s*" % (prefix, empty_message)
+
+
+def _dataset_provenance(gi, history_id, id):
+    provenance = gi.histories.show_dataset_provenance(history_id, id)
+    return provenance
+
+
 __all__ = (
     "DEFAULT_MASTER_API_KEY",
     "gi",
diff --git a/planemo/galaxy/config.py b/planemo/galaxy/config.py
index 736491ad7..82f90d3a8 100644
--- a/planemo/galaxy/config.py
+++ b/planemo/galaxy/config.py
@@ -442,6 +442,7 @@ def config_join(*args):
             ftp_upload_purge="False",
             ftp_upload_dir=test_data_dir or os.path.abspath('.'),
             ftp_upload_site="Test Data",
+            check_upload_content="False",
             allow_path_paste="True",
             tool_dependency_dir=dependency_dir,
             file_path=file_path,
diff --git a/requirements.txt b/requirements.txt
index 2485b09fb..2ae7890b6 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -13,6 +13,6 @@ virtualenv
 lxml
 gxformat2>=0.1.1
 ephemeris>=0.2.0
-galaxy-lib>=17.9.6
+galaxy-lib>=17.9.7
 html5lib>=0.9999999,!=0.99999999,!=0.999999999,!=1.0b10,!=1.0b09
 cwltool==1.0.20170828135420