diff --git a/client/src/components/Upload/DefaultBox.vue b/client/src/components/Upload/DefaultBox.vue
index 5182b087a306..4afaa63ad705 100644
--- a/client/src/components/Upload/DefaultBox.vue
+++ b/client/src/components/Upload/DefaultBox.vue
@@ -58,7 +58,7 @@ const props = defineProps({
     },
     lazyLoad: {
         type: Number,
-        default: 50,
+        default: 150,
     },
     listDbKeys: {
         type: Array,
@@ -84,6 +84,7 @@ const uploadCompleted = ref(0);
 const uploadFile = ref(null);
 const uploadItems = ref({});
 const uploadSize = ref(0);
+const queue = ref(createUploadQueue());
 
 const counterNonRunning = computed(() => counterAnnounce.value + counterSuccess.value + counterError.value);
 const enableBuild = computed(
@@ -99,8 +100,6 @@ const listExtensions = computed(() => props.effectiveExtensions.filter((ext) =>
 const showHelper = computed(() => Object.keys(uploadItems.value).length === 0);
 const uploadValues = computed(() => Object.values(uploadItems.value));
 
-const queue = computed(() => createUploadQueue());
-
 function createUploadQueue() {
     return new UploadQueue({
         announce: eventAnnounce,
@@ -108,7 +107,6 @@ function createUploadQueue() {
         complete: eventComplete,
         error: eventError,
         get: (index) => uploadItems.value[index],
-        historyId: historyId.value,
         multiple: props.multiple,
         progress: eventProgress,
         success: eventSuccess,
@@ -268,6 +266,11 @@ function eventStart() {
         uploadValues.value.forEach((model) => {
             if (model.status === "init") {
                 model.status = "queued";
+                if (!model.targetHistoryId) {
+                    // Associate with current history once upload starts
+                    // This will not change if the current history is changed during upload
+                    model.targetHistoryId = historyId.value;
+                }
                 uploadSize.value += model.fileSize;
             }
         });
diff --git a/client/src/components/Upload/UploadModal.vue b/client/src/components/Upload/UploadModal.vue
index 762abcc9afc0..a78b0ce0adea 100644
--- a/client/src/components/Upload/UploadModal.vue
+++ b/client/src/components/Upload/UploadModal.vue
@@ -1,17 +1,17 @@
 <script setup>
-import { setIframeEvents } from "components/Upload/utils";
-import { useConfig } from "composables/config";
-import { useUserHistories } from "composables/userHistories";
 import { storeToRefs } from "pinia";
 import { ref, watch } from "vue";
 
+import { setIframeEvents } from "@/components/Upload/utils";
+import { useConfig } from "@/composables/config";
+import { useUserHistories } from "@/composables/userHistories";
 import { useUserStore } from "@/stores/userStore";
 import { wait } from "@/utils/utils";
 
 import UploadContainer from "./UploadContainer.vue";
 
 const { currentUser } = storeToRefs(useUserStore());
-const { currentHistoryId } = useUserHistories(currentUser);
+const { currentHistoryId, currentHistory } = useUserHistories(currentUser);
 
 const { config, isConfigLoaded } = useConfig();
 
@@ -81,7 +81,12 @@ defineExpose({
         no-enforce-focus
         hide-footer>
         <template v-slot:modal-header>
-            <h2 class="title h-sm" tabindex="0">{{ options.title }}</h2>
+            <h2 class="title h-sm" tabindex="0">
+                {{ options.title }}
+                <span v-if="currentHistory">
+                    to <b>{{ currentHistory.name }}</b>
+                </span>
+            </h2>
         </template>
         <UploadContainer
             v-if="currentHistoryId"
diff --git a/client/src/composables/userHistories.js b/client/src/composables/userHistories.js
index ae8376527e83..823e66c45bef 100644
--- a/client/src/composables/userHistories.js
+++ b/client/src/composables/userHistories.js
@@ -15,6 +15,10 @@ export function useUserHistories(user) {
     );
 
     const currentHistoryId = computed(() => historyStore.currentHistoryId);
+    const currentHistory = computed(() => historyStore.currentHistory);
 
-    return { currentHistoryId };
+    return {
+        currentHistoryId,
+        currentHistory,
+    };
 }
diff --git a/client/src/utils/upload-queue.js b/client/src/utils/upload-queue.js
index 854ae90de567..d4d10b46e9da 100644
--- a/client/src/utils/upload-queue.js
+++ b/client/src/utils/upload-queue.js
@@ -96,7 +96,11 @@ export class UploadQueue {
             // Remove item from queue
             this.remove(index);
             // Collect upload request data
-            const data = uploadPayload([this.opts.get(index)], this.opts.historyId);
+            const item = this.opts.get(index);
+            if (!item.targetHistoryId) {
+                throw new Error(`Missing target history for upload item [${index}] ${item.fileName}`);
+            }
+            const data = uploadPayload([item], item.targetHistoryId);
             // Initiate upload request
             this._processSubmit(index, data);
         } catch (e) {
@@ -107,19 +111,27 @@ export class UploadQueue {
         }
     }
 
-    // Submit remote files as single batch request
+    // Submit remote files as single batch request per target history
     _processUrls() {
-        const list = [];
+        const batchByHistory = {};
         for (const index of this.queue.keys()) {
             const model = this.opts.get(index);
             if (model.status === "queued" && model.fileMode === "url") {
-                list.push({ index, ...model });
+                if (!model.targetHistoryId) {
+                    throw new Error(`Missing target history for upload item [${index}] ${model.fileName}`);
+                }
+                if (!batchByHistory[model.targetHistoryId]) {
+                    batchByHistory[model.targetHistoryId] = [];
+                }
+                batchByHistory[model.targetHistoryId].push({ index, ...model });
                 this.remove(index);
             }
         }
-        if (list.length > 0) {
+
+        for (const historyId in batchByHistory) {
+            const list = batchByHistory[historyId];
             try {
-                const data = uploadPayload(list, this.opts.historyId);
+                const data = uploadPayload(list, historyId);
                 sendPayload(data, {
                     success: (message) => {
                         list.forEach((model) => {
diff --git a/client/src/utils/upload-queue.test.js b/client/src/utils/upload-queue.test.js
index 473d578dd1da..3e5a72588132 100644
--- a/client/src/utils/upload-queue.test.js
+++ b/client/src/utils/upload-queue.test.js
@@ -177,6 +177,7 @@ describe("UploadQueue", () => {
                     spaceToTab: true,
                     status: "queued",
                     toPosixLines: false,
+                    targetHistoryId: "historyId",
                 };
             },
             get: (index) => fileEntries[index],
diff --git a/lib/galaxy/celery/tasks.py b/lib/galaxy/celery/tasks.py
index e1ac7456ad41..3b2e4c6272a7 100644
--- a/lib/galaxy/celery/tasks.py
+++ b/lib/galaxy/celery/tasks.py
@@ -185,14 +185,19 @@ def set_metadata(
     dataset_id: int,
     model_class: str = "HistoryDatasetAssociation",
     overwrite: bool = True,
+    ensure_can_set_metadata: bool = True,
     task_user_id: Optional[int] = None,
 ):
+    """
+    ensure_can_set_metadata can be bypassed for new outputs.
+    """
     manager = _get_dataset_manager(hda_manager, ldda_manager, model_class)
     dataset_instance = manager.by_id(dataset_id)
-    can_set_metadata = manager.ensure_can_set_metadata(dataset_instance, raiseException=False)
-    if not can_set_metadata:
-        log.info(f"Setting metadata is not allowed for {model_class} {dataset_instance.id}")
-        return
+    if ensure_can_set_metadata:
+        can_set_metadata = manager.ensure_can_set_metadata(dataset_instance, raiseException=False)
+        if not can_set_metadata:
+            log.info(f"Setting metadata is not allowed for {model_class} {dataset_instance.id}")
+            return
     try:
         if overwrite:
             hda_manager.overwrite_metadata(dataset_instance)
diff --git a/lib/galaxy/jobs/__init__.py b/lib/galaxy/jobs/__init__.py
index 64ffcd29b022..f58fa84b95ad 100644
--- a/lib/galaxy/jobs/__init__.py
+++ b/lib/galaxy/jobs/__init__.py
@@ -2020,8 +2020,9 @@ def fail(message=job.info, exception=None):
         # Certain tools require tasks to be completed after job execution
         # ( this used to be performed in the "exec_after_process" hook, but hooks are deprecated ).
         param_dict = self.get_param_dict(job)
+        task_wrapper = None
         try:
-            self.tool.exec_after_process(
+            task_wrapper = self.tool.exec_after_process(
                 self.app, inp_data, out_data, param_dict, job=job, final_job_state=final_job_state
             )
         except Exception as e:
@@ -2063,6 +2064,10 @@ def fail(message=job.info, exception=None):
             self.sa_session.commit()
         if job.state == job.states.ERROR:
             self._report_error()
+        elif task_wrapper:
+            # Only task is setting metadata (if necessary) on expression tool output.
+            # The dataset state is SETTING_METADATA, which delays dependent jobs until the task completes.
+            task_wrapper.delay()
         cleanup_job = self.cleanup_job
         delete_files = cleanup_job == "always" or (job.state == job.states.OK and cleanup_job == "onsuccess")
         self.cleanup(delete_files=delete_files)
diff --git a/lib/galaxy/tools/__init__.py b/lib/galaxy/tools/__init__.py
index 21b6f6cc71f8..7193fd6ea618 100644
--- a/lib/galaxy/tools/__init__.py
+++ b/lib/galaxy/tools/__init__.py
@@ -2929,7 +2929,27 @@ def exec_after_process(self, app, inp_data, out_data, param_dict, job=None, **kw
                         break
                 if copy_object is None:
                     raise exceptions.MessageException("Failed to find dataset output.")
-                out_data[key].copy_from(copy_object, include_metadata=True)
+                output = out_data[key]
+                # if change_datatype PJA is associated with expression tool output the new output already has
+                # the desired datatype, so we use it. If the extension is "data" there's no change_dataset PJA and
+                # we want to use the existing extension.
+                new_ext = output.extension if output.extension != "data" else copy_object.extension
+                require_metadata_regeneration = copy_object.extension != new_ext
+                output.copy_from(copy_object, include_metadata=not require_metadata_regeneration)
+                output.extension = new_ext
+                if require_metadata_regeneration:
+                    if app.config.enable_celery_tasks:
+                        from galaxy.celery.tasks import set_metadata
+
+                        output._state = model.Dataset.states.SETTING_METADATA
+                        return set_metadata.si(
+                            dataset_id=output.id, task_user_id=output.history.user_id, ensure_can_set_metadata=False
+                        )
+                    else:
+                        # TODO: move exec_after_process into metadata script so this doesn't run on the headnode ?
+                        output.init_meta()
+                        output.set_meta()
+                        output.set_metadata_success_state()
 
     def parse_environment_variables(self, tool_source):
         """Setup environment variable for inputs file."""
diff --git a/lib/galaxy/webapps/galaxy/controllers/admin.py b/lib/galaxy/webapps/galaxy/controllers/admin.py
index 7e788bb1cc0f..bd0ea3a06158 100644
--- a/lib/galaxy/webapps/galaxy/controllers/admin.py
+++ b/lib/galaxy/webapps/galaxy/controllers/admin.py
@@ -73,7 +73,7 @@ def sort(self, trans, query, ascending, column_name=None):
                 .group_by(model.GalaxySession.table.c.user_id)
                 .subquery()
             )
-            query = query.outerjoin((last_login_subquery, model.User.table.c.id == last_login_subquery.c.user_id))
+            query = query.outerjoin(last_login_subquery, model.User.table.c.id == last_login_subquery.c.user_id)
 
             if not ascending:
                 query = query.order_by((last_login_subquery.c.last_login).desc().nullslast())
diff --git a/lib/galaxy_test/api/test_workflows.py b/lib/galaxy_test/api/test_workflows.py
index 88d4112966fd..b09723b71fd1 100644
--- a/lib/galaxy_test/api/test_workflows.py
+++ b/lib/galaxy_test/api/test_workflows.py
@@ -2056,14 +2056,25 @@ def test_run_workflow_pick_value_bam_pja(self):
           pick_from:
           - value:
             __class__: RuntimeValue
+  consume_index:
+    tool_id: metadata_bam
+    in:
+      input_bam: pick_value/data_param
+    tool_state:
+      ref_names:
+        - chr10_random
+        - chr11
+        - chrM
+        - chrX
+        - chr16
 outputs:
   pick_out:
     outputSource: pick_value/data_param
 """,
                 test_data="""
 some_file:
-  value: 1.bam
-  file_type: bam
+  value: 3.bam
+  file_type: unsorted.bam
   type: File
 """,
                 history_id=history_id,
@@ -2076,6 +2087,7 @@ def test_run_workflow_pick_value_bam_pja(self):
         )
         assert dataset_details["metadata_reference_names"]
         assert dataset_details["metadata_bam_index"]
+        assert dataset_details["file_ext"] == "bam"
 
     def test_run_workflow_simple_conditional_step(self):
         with self.dataset_populator.test_history() as history_id: