diff --git a/temporalio/lib/temporalio/contrib/open_telemetry.rb b/temporalio/lib/temporalio/contrib/open_telemetry.rb
index 5838b5cf..a894e300 100644
--- a/temporalio/lib/temporalio/contrib/open_telemetry.rb
+++ b/temporalio/lib/temporalio/contrib/open_telemetry.rb
@@ -23,6 +23,11 @@ class TracingInterceptor
         # @param tracer [OpenTelemetry::Trace::Tracer] Tracer to use.
         # @param header_key [String] Temporal header name to serialize spans to/from. Most users should not change this.
         # @param propagator [Object] Propagator to use. Most users should not change this.
+        # @param always_create_workflow_spans [Boolean] When false, the default, spans are only created in workflows
+        #   when an overarching span from the client is present. In cases of starting a workflow elsewhere, e.g. CLI or
+        #   schedules, a client-created span is not present and workflow spans will not be created. Setting this to true
+        #   will create spans in workflows no matter what, but there is a risk of them being orphans since they may not
+        #   have a parent span after replaying.
         def initialize(
           tracer,
           header_key: '_tracer-data',
@@ -31,11 +36,13 @@ def initialize(
               ::OpenTelemetry::Trace::Propagation::TraceContext::TextMapPropagator.new,
               ::OpenTelemetry::Baggage::Propagation::TextMapPropagator.new
             ]
-          )
+          ),
+          always_create_workflow_spans: false
         )
           @tracer = tracer
           @header_key = header_key
           @propagator = propagator
+          @always_create_workflow_spans = always_create_workflow_spans
         end
 
         # @!visibility private
@@ -85,6 +92,11 @@ def _with_started_span(
           end
         end
 
+        # @!visibility private
+        def _always_create_workflow_spans
+          @always_create_workflow_spans
+        end
+
         # @!visibility private
         class ClientOutbound < Client::Interceptor::Outbound
           def initialize(root, next_interceptor)
@@ -423,30 +435,34 @@ def self.completed_span(
           even_during_replay: false
         )
           # Get root interceptor, which also checks if in workflow
-          root = Temporalio::Workflow.storage[:__temporal_opentelemetry_tracing_interceptor]
+          root = Temporalio::Workflow.storage[:__temporal_opentelemetry_tracing_interceptor] #: TracingInterceptor?
           raise 'Tracing interceptor not configured' unless root
 
           # Do nothing if replaying and not wanted during replay
           return nil if !even_during_replay && Temporalio::Workflow::Unsafe.replaying?
 
-          # Do nothing if there is no span on the context. We do not want orphan spans coming from workflows, so we
-          # require a parent (i.e. a current).
-          # TODO(cretz): This matches Python behavior but not .NET behavior (which will create no matter what), is that
-          # ok?
-          return nil if ::OpenTelemetry::Trace.current_span == ::OpenTelemetry::Trace::Span::INVALID
+          # If there is no span on the context and the user hasn't opted in to always creating, do not create. This
+          # prevents orphans if there was no span originally created from the client start-workflow call.
+          if ::OpenTelemetry::Trace.current_span == ::OpenTelemetry::Trace::Span::INVALID &&
+             !root._always_create_workflow_spans
+            return nil
+          end
 
           # Create attributes, adding user-defined ones
           attributes = { 'temporalWorkflowID' => Temporalio::Workflow.info.workflow_id,
                          'temporalRunID' => Temporalio::Workflow.info.run_id }.merge(attributes)
 
-          # Create span
-          time = Temporalio::Workflow.now
-          timestamp = (time.to_i * 1_000_000_000) + time.nsec
-          span = root.tracer.start_span(name, attributes:, links:, start_timestamp: timestamp, kind:) # steep:ignore
-          # Record exception if present
-          span.record_exception(exception) if exception
-          # Finish the span (returns self)
-          span.finish(end_timestamp: timestamp)
+          # Create span, which has to be done with illegal call disabling because OTel asks for full exception message
+          # which uses error highlighting and such which accesses File#path
+          Temporalio::Workflow::Unsafe.illegal_call_tracing_disabled do
+            time = Temporalio::Workflow.now
+            timestamp = (time.to_i * 1_000_000_000) + time.nsec
+            span = root.tracer.start_span(name, attributes:, links:, start_timestamp: timestamp, kind:) # steep:ignore
+            # Record exception if present
+            span.record_exception(exception) if exception
+            # Finish the span (returns self)
+            span.finish(end_timestamp: timestamp)
+          end
         end
       end
     end
diff --git a/temporalio/sig/temporalio/contrib/open_telemetry.rbs b/temporalio/sig/temporalio/contrib/open_telemetry.rbs
index a0c60416..de2158cf 100644
--- a/temporalio/sig/temporalio/contrib/open_telemetry.rbs
+++ b/temporalio/sig/temporalio/contrib/open_telemetry.rbs
@@ -11,7 +11,8 @@ module Temporalio
         def initialize: (
           untyped tracer,
           ?header_key: String,
-          ?propagator: untyped
+          ?propagator: untyped,
+          ?always_create_workflow_spans: bool
         ) -> void
 
         def _apply_context_to_headers: (Hash[String, untyped] headers, ?context: untyped) -> void
@@ -23,6 +24,7 @@ module Temporalio
           ?attributes: Hash[untyped, untyped]?,
           ?outbound_input: untyped
         ) { () -> T } -> T
+        def _always_create_workflow_spans: -> bool
 
         class WorkflowInbound < Worker::Interceptor::Workflow::Inbound
           def initialize: (TracingInterceptor root, Worker::Interceptor::Workflow::Inbound next_interceptor) -> void
diff --git a/temporalio/test/contrib/open_telemetry_test.rb b/temporalio/test/contrib/open_telemetry_test.rb
index 0c64e83c..e8dd7a57 100644
--- a/temporalio/test/contrib/open_telemetry_test.rb
+++ b/temporalio/test/contrib/open_telemetry_test.rb
@@ -96,10 +96,12 @@ def update(scenario)
           ) do
             Temporalio::Workflow.execute_local_activity(TestActivity, :fail_first_attempt, start_to_close_timeout: 30)
           end
-        when :child_workflow
-          # Start a child, send child signal and external signal, finish
+        when :child_workflow_child_signal
+          handle = Temporalio::Workflow.start_child_workflow(TestWorkflow, :wait_on_signal)
+          handle.signal(TestWorkflow.signal, :mark_finished)
+          [handle.id, handle.first_execution_run_id, handle.result]
+        when :child_workflow_external_signal
           handle = Temporalio::Workflow.start_child_workflow(TestWorkflow, :wait_on_signal)
-          handle.signal(TestWorkflow.signal, :complete)
           Temporalio::Workflow.external_workflow_handle(handle.id).signal(TestWorkflow.signal, :mark_finished)
           [handle.id, handle.first_execution_run_id, handle.result]
         else
@@ -138,11 +140,18 @@ def init_tracer_and_exporter
       [tracer, exporter]
     end
 
-    def trace(tracer_and_exporter: init_tracer_and_exporter, &)
+    def trace(
+      tracer_and_exporter: init_tracer_and_exporter,
+      always_create_workflow_spans: false,
+      check_root: true,
+      &
+    )
       tracer, exporter = tracer_and_exporter
 
       # Make client with interceptors
-      interceptor = Temporalio::Contrib::OpenTelemetry::TracingInterceptor.new(tracer)
+      interceptor = Temporalio::Contrib::OpenTelemetry::TracingInterceptor.new(
+        tracer, always_create_workflow_spans:
+      )
       new_options = env.client.options.with(interceptors: [interceptor])
       client = Temporalio::Client.new(**new_options.to_h) # steep:ignore
 
@@ -153,13 +162,22 @@ def trace(tracer_and_exporter: init_tracer_and_exporter, &)
 
       # Convert spans, confirm there is only the outer, and return children
       spans = ExpectedSpan.from_span_data(exporter.finished_spans)
-      assert_equal 1, spans.size
-      assert_equal 'root', spans.first&.name
+      if check_root
+        assert_equal 1, spans.size
+        assert_equal 'root', spans.first&.name
+      end
       spans.first
     end
 
-    def trace_workflow(scenario, tracer_and_exporter: init_tracer_and_exporter, &)
-      trace(tracer_and_exporter:) do |client|
+    def trace_workflow(
+      scenario,
+      tracer_and_exporter: init_tracer_and_exporter,
+      start_with_untraced_client: false,
+      always_create_workflow_spans: false,
+      check_root: true,
+      &
+    )
+      trace(tracer_and_exporter:, always_create_workflow_spans:, check_root:) do |client|
         # Must capture and attach outer context
         outer_context = OpenTelemetry::Context.current
         attach_token = nil
@@ -169,7 +187,8 @@ def trace_workflow(scenario, tracer_and_exporter: init_tracer_and_exporter, &)
           client:,
           activities: [TestActivity.new(tracer_and_exporter.first)],
           # Have to reattach outer context inside worker run to check outer span
-          on_worker_run: proc { attach_token = OpenTelemetry::Context.attach(outer_context) }
+          on_worker_run: proc { attach_token = OpenTelemetry::Context.attach(outer_context) },
+          start_workflow_client: start_with_untraced_client ? env.client : client
         ) do |handle|
           yield handle
         ensure
@@ -398,42 +417,61 @@ def test_client_fail
     end
 
     def test_child_and_external
-      exp_root = ExpectedSpan.new(name: 'root')
-      act_root = trace_workflow(:wait_on_signal) do |handle|
-        exp_cl_attrs = { 'temporalWorkflowID' => handle.id }
-        exp_run_attrs = exp_cl_attrs.merge({ 'temporalRunID' => handle.result_run_id })
-        exp_start_wf = exp_root.add_child(name: 'StartWorkflow:TestWorkflow', attributes: exp_cl_attrs)
-        exp_start_wf.add_child(name: 'RunWorkflow:TestWorkflow', attributes: exp_run_attrs)
-
-        # Wait for task completion so update isn't accidentally first before run
-        assert_eventually { assert handle.fetch_history_events.any?(&:workflow_task_completed_event_attributes) }
-
-        # Update calls child and sends signals to it in two ways
-        child_id, child_run_id, child_result = handle.execute_update(TestWorkflow.update,
-                                                                     :child_workflow, id: 'my-update-id')
-        exp_update = exp_root.add_child(name: 'StartWorkflowUpdate:update',
-                                        attributes: exp_cl_attrs.merge({ 'temporalUpdateID' => 'my-update-id' }))
-        # Expected span for update
-        exp_hnd_update = exp_start_wf.add_child(
-          name: 'HandleUpdate:update',
-          attributes: exp_run_attrs.merge({ 'temporalUpdateID' => 'my-update-id' }),
-          links: [exp_update]
-        )
-        # Expected for children
-        exp_child_run_attrs = { 'temporalWorkflowID' => child_id, 'temporalRunID' => child_run_id }
-        exp_child_start = exp_hnd_update.add_child(name: 'StartChildWorkflow:TestWorkflow', attributes: exp_run_attrs)
-        exp_child_start
-          .add_child(name: 'RunWorkflow:TestWorkflow', attributes: exp_child_run_attrs)
-          .add_child(name: 'CompleteWorkflow:TestWorkflow', attributes: exp_child_run_attrs)
-        # Two signals we send to the child
-        exp_sig_child = exp_hnd_update.add_child(name: 'SignalChildWorkflow:signal', attributes: exp_run_attrs)
-        exp_sig_ext = exp_hnd_update.add_child(name: 'SignalExternalWorkflow:signal', attributes: exp_run_attrs)
-        exp_child_start.add_child(name: 'HandleSignal:signal', attributes: exp_child_run_attrs, links: [exp_sig_child])
-        exp_child_start.add_child(name: 'HandleSignal:signal', attributes: exp_child_run_attrs, links: [exp_sig_ext])
-
-        assert_equal 'workflow-done', child_result
+      # We have to test child signal and external signal separately because sending both back-to-back can result in
+      # rare cases where one is delivered before the other (yes, even if you wait on the first to get an initiated
+      # event)
+      %i[child_workflow_child_signal child_workflow_external_signal].each do |scenario|
+        exp_root = ExpectedSpan.new(name: 'root')
+        act_root = trace_workflow(:wait_on_signal) do |handle|
+          exp_cl_attrs = { 'temporalWorkflowID' => handle.id }
+          exp_run_attrs = exp_cl_attrs.merge({ 'temporalRunID' => handle.result_run_id })
+          exp_start_wf = exp_root.add_child(name: 'StartWorkflow:TestWorkflow', attributes: exp_cl_attrs)
+          exp_start_wf.add_child(name: 'RunWorkflow:TestWorkflow', attributes: exp_run_attrs)
+
+          # Wait for task completion so update isn't accidentally first before run
+          assert_eventually { assert handle.fetch_history_events.any?(&:workflow_task_completed_event_attributes) }
+
+          # Update calls child and sends signals to it in two ways
+          child_id, child_run_id, child_result = handle.execute_update(TestWorkflow.update,
+                                                                       scenario, id: 'my-update-id')
+          exp_update = exp_root.add_child(name: 'StartWorkflowUpdate:update',
+                                          attributes: exp_cl_attrs.merge({ 'temporalUpdateID' => 'my-update-id' }))
+          # Expected span for update
+          exp_hnd_update = exp_start_wf.add_child(
+            name: 'HandleUpdate:update',
+            attributes: exp_run_attrs.merge({ 'temporalUpdateID' => 'my-update-id' }),
+            links: [exp_update]
+          )
+          # Expected for children
+          exp_child_run_attrs = { 'temporalWorkflowID' => child_id, 'temporalRunID' => child_run_id }
+          exp_child_start = exp_hnd_update.add_child(name: 'StartChildWorkflow:TestWorkflow', attributes: exp_run_attrs)
+          exp_child_start
+            .add_child(name: 'RunWorkflow:TestWorkflow', attributes: exp_child_run_attrs)
+            .add_child(name: 'CompleteWorkflow:TestWorkflow', attributes: exp_child_run_attrs)
+
+          # There are cases where signal comes _before_ start and cases where signal _comes_ after and server gives us
+          # no way of knowing that a child _actually_ began running, so we check whether task completed comes before
+          # signal
+          assert_equal 'workflow-done', child_result
+          child_events = env.client.workflow_handle(child_id.to_s).fetch_history_events.to_a
+          signal_comes_first = child_events.index(&:workflow_execution_signaled_event_attributes).to_i <
+                               child_events.index(&:workflow_task_completed_event_attributes).to_i
+          # Signal we send to the child
+          exp_sig = if scenario == :child_workflow_child_signal
+                      exp_hnd_update.add_child(name: 'SignalChildWorkflow:signal', attributes: exp_run_attrs)
+                    else
+                      exp_hnd_update.add_child(name: 'SignalExternalWorkflow:signal', attributes: exp_run_attrs)
+                    end
+          exp_child_start.add_child(
+            name: 'HandleSignal:signal',
+            attributes: exp_child_run_attrs,
+            links: [exp_sig],
+            insert_at: signal_comes_first ? 0 : 1
+          )
+        end
+        assert_equal exp_root.to_s_indented, act_root.to_s_indented,
+                     "Expected:\n#{exp_root.to_s_indented}\nActual:#{act_root.to_s_indented}"
       end
-      assert_equal exp_root.to_s_indented, act_root.to_s_indented
     end
 
     def test_continue_as_new
@@ -458,6 +496,29 @@ def test_continue_as_new
       assert_equal exp_root.to_s_indented, act_root.to_s_indented
     end
 
+    def test_always_create_workflow_spans
+      # Untraced client has no spans by default
+      act = trace_workflow(:complete, start_with_untraced_client: true, check_root: false) do |handle|
+        assert_equal 'workflow-done', handle.result
+      end
+      assert_empty act.children
+
+      # Untraced client has no spans by default
+      exp_root = ExpectedSpan.new(name: 'root')
+      act = trace_workflow(
+        :complete,
+        start_with_untraced_client: true,
+        always_create_workflow_spans: true,
+        check_root: false
+      ) do |handle|
+        exp_attrs = { 'temporalWorkflowID' => handle.id, 'temporalRunID' => handle.result_run_id }
+        exp_run_wf = exp_root.add_child(name: 'RunWorkflow:TestWorkflow', attributes: exp_attrs)
+        exp_run_wf.add_child(name: 'CompleteWorkflow:TestWorkflow', attributes: exp_attrs)
+        assert_equal 'workflow-done', handle.result
+      end
+      assert_equal exp_root.children.first&.to_s_indented, act.to_s_indented
+    end
+
     ExpectedSpan = Data.define(:name, :children, :attributes, :links, :exception_message) # rubocop:disable Layout/ClassStructure
 
     class ExpectedSpan
@@ -493,13 +554,16 @@ def self.from_span_data(all_spans)
       end
 
       def initialize(name:, children: [], attributes: {}, links: [], exception_message: nil)
-        children = children.to_set
         super
       end
 
-      def add_child(name:, attributes: {}, links: [], exception_message: nil)
+      def add_child(name:, attributes: {}, links: [], exception_message: nil, insert_at: nil)
         span = ExpectedSpan.new(name:, attributes:, links:, exception_message:)
-        children << span
+        if insert_at.nil?
+          children << span
+        else
+          children.insert(insert_at, span)
+        end
         span
       end
 
diff --git a/temporalio/test/sig/contrib/open_telemetry_test.rbs b/temporalio/test/sig/contrib/open_telemetry_test.rbs
index d7d32bd5..9043264d 100644
--- a/temporalio/test/sig/contrib/open_telemetry_test.rbs
+++ b/temporalio/test/sig/contrib/open_telemetry_test.rbs
@@ -2,11 +2,16 @@ module Contrib
   class OpenTelemetryTest < Test
     def init_tracer_and_exporter: -> [untyped, untyped]
     def trace: (
-      ?tracer_and_exporter: [untyped, untyped]
+      ?tracer_and_exporter: [untyped, untyped],
+      ?always_create_workflow_spans: bool,
+      ?check_root: bool
     ) { (Temporalio::Client) -> void } -> untyped
     def trace_workflow: (
       Symbol scenario,
-      ?tracer_and_exporter: [untyped, untyped]
+      ?tracer_and_exporter: [untyped, untyped],
+      ?start_with_untraced_client: bool,
+      ?always_create_workflow_spans: bool,
+      ?check_root: bool
     ) { (Temporalio::Client::WorkflowHandle) -> void } -> untyped
 
     class ExpectedSpan
@@ -30,7 +35,8 @@ module Contrib
         name: String,
         ?attributes: Hash[untyped, untyped],
         ?links: Array[ExpectedSpan],
-        ?exception_message: String?
+        ?exception_message: String?,
+        ?insert_at: Integer?
       ) -> ExpectedSpan
 
       def to_s_indented: (?indent: String) -> String
diff --git a/temporalio/test/sig/workflow_utils.rbs b/temporalio/test/sig/workflow_utils.rbs
index 3b7144fa..42e2853d 100644
--- a/temporalio/test/sig/workflow_utils.rbs
+++ b/temporalio/test/sig/workflow_utils.rbs
@@ -17,7 +17,8 @@ module WorkflowUtils
     ?id_conflict_policy: Temporalio::WorkflowIDConflictPolicy::enum,
     ?max_heartbeat_throttle_interval: Float,
     ?task_timeout: duration?,
-    ?on_worker_run: Proc?
+    ?on_worker_run: Proc?,
+    ?start_workflow_client: Temporalio::Client
   ) -> Object? |
   [T] (
     singleton(Temporalio::Workflow::Definition) workflow,
@@ -37,7 +38,8 @@ module WorkflowUtils
     ?id_conflict_policy: Temporalio::WorkflowIDConflictPolicy::enum,
     ?max_heartbeat_throttle_interval: Float,
     ?task_timeout: duration?,
-    ?on_worker_run: Proc?
+    ?on_worker_run: Proc?,
+    ?start_workflow_client: Temporalio::Client
   ) { (Temporalio::Client::WorkflowHandle, Temporalio::Worker) -> T } -> T
 
   def assert_eventually_task_fail: (
diff --git a/temporalio/test/workflow_utils.rb b/temporalio/test/workflow_utils.rb
index ea0c914b..973e1ecf 100644
--- a/temporalio/test/workflow_utils.rb
+++ b/temporalio/test/workflow_utils.rb
@@ -29,7 +29,8 @@ def execute_workflow(
     max_heartbeat_throttle_interval: 60.0,
     task_timeout: nil,
     interceptors: [],
-    on_worker_run: nil
+    on_worker_run: nil,
+    start_workflow_client: client
   )
     worker = Temporalio::Worker.new(
       client:,
@@ -45,7 +46,7 @@ def execute_workflow(
     )
     worker.run do
       on_worker_run&.call
-      handle = client.start_workflow(
+      handle = start_workflow_client.start_workflow(
         workflow,
         *args,
         id:,