diff --git a/client/src/components/Form/FormDisplay.vue b/client/src/components/Form/FormDisplay.vue
index bad270f506e..31d209317f4 100644
--- a/client/src/components/Form/FormDisplay.vue
+++ b/client/src/components/Form/FormDisplay.vue
@@ -127,8 +127,19 @@ export default {
     },
     created() {
         this.onCloneInputs();
+        // build flat formData that is ready to be submitted
+        this.formData = this.buildFormData();
+        // emit back to parent, so that parent has submittable data
+        this.$emit("onChange", this.formData);
     },
     methods: {
+        buildFormData() {
+            const params = {};
+            Object.entries(this.formIndex).forEach(([key, input]) => {
+                params[key] = input.value;
+            });
+            return params;
+        },
         onReplaceParams() {
             let refreshOnChange = false;
             Object.entries(this.replaceParams).forEach(([key, value]) => {
@@ -159,10 +170,7 @@ export default {
         },
         onChange(refreshOnChange) {
             this.onCreateIndex();
-            const params = {};
-            Object.entries(this.formIndex).forEach(([key, input]) => {
-                params[key] = input.value;
-            });
+            const params = this.buildFormData();
             if (JSON.stringify(params) != JSON.stringify(this.formData)) {
                 this.formData = params;
                 this.resetError();
diff --git a/client/src/components/Form/FormElement.test.js b/client/src/components/Form/FormElement.test.js
index 79a7770442f..1339639961c 100644
--- a/client/src/components/Form/FormElement.test.js
+++ b/client/src/components/Form/FormElement.test.js
@@ -49,11 +49,10 @@ describe("FormElement", () => {
         });
         expect(wrapper.find(".ui-form-title-text").text()).toEqual("title_text");
         expect(wrapper.findAll("button[title='Disable']").length).toEqual(1);
-        expect(wrapper.emitted().input[0][0]).toEqual("initial_value");
 
         await wrapper.find(".ui-form-collapsible-icon").trigger("click");
-        expect(wrapper.emitted().input[1][0]).toEqual("collapsible_value");
-        expect(wrapper.emitted().input[1][1]).toEqual("input");
+        expect(wrapper.emitted().input[0][0]).toEqual("collapsible_value");
+        expect(wrapper.emitted().input[0][1]).toEqual("input");
 
         await wrapper.setProps({
             collapsedEnableText: "Enable Collapsible",
@@ -63,7 +62,7 @@ describe("FormElement", () => {
         expect(wrapper.findAll("button[title='Disable Collapsible']").length).toEqual(0);
 
         await wrapper.find(".ui-form-collapsible-icon").trigger("click");
-        expect(wrapper.emitted().input[2][0]).toEqual("default_value");
+        expect(wrapper.emitted().input[1][0]).toEqual("default_value");
         expect(wrapper.findAll("button[title='Disable Collapsible']").length).toEqual(1);
         expect(wrapper.findAll("button[title='Enable Collapsible']").length).toEqual(0);
     });
diff --git a/client/src/components/Form/FormElement.vue b/client/src/components/Form/FormElement.vue
index ecc6fa340a7..4645ad6a5a8 100644
--- a/client/src/components/Form/FormElement.vue
+++ b/client/src/components/Form/FormElement.vue
@@ -82,9 +82,8 @@ const collapsed = ref(false);
 const collapsible = computed(() => !props.disabled && collapsibleValue.value !== undefined);
 const connectable = computed(() => collapsible.value && Boolean(attrs.value["connectable"]));
 
-// Determines to wether expand or collapse the input
+// Determines whether to expand or collapse the input
 {
-    setValue(props.value);
     const valueJson = JSON.stringify(props.value);
     connected.value = valueJson === JSON.stringify(connectedValue);
     collapsed.value =
diff --git a/client/src/components/History/CurrentCollection/CollectionPanel.vue b/client/src/components/History/CurrentCollection/CollectionPanel.vue
index eb69d0ee598..fcc6942e9ce 100644
--- a/client/src/components/History/CurrentCollection/CollectionPanel.vue
+++ b/client/src/components/History/CurrentCollection/CollectionPanel.vue
@@ -4,6 +4,7 @@
     <CollectionElementsProvider
         v-if="dsc"
         :id="dsc.id"
+        ref="provider"
         :key="dsc.id"
         v-slot="{ loading, result: payload }"
         :contents-url="contentsUrl"
@@ -76,6 +77,9 @@ export default {
             const arr = this.selectedCollections;
             return arr[arr.length - 1];
         },
+        jobState() {
+            return this.dsc["job_state_summary"];
+        },
         isRoot() {
             return this.dsc == this.rootCollection;
         },
@@ -93,6 +97,12 @@ export default {
                 this.$emit("update:selected-collections", []);
             }
         },
+        jobState: {
+            handler() {
+                this.$refs.provider.load();
+            },
+            deep: true,
+        },
     },
     methods: {
         updateDsc(collection, fields) {
diff --git a/client/src/components/Masthead/_webhooks.js b/client/src/components/Masthead/_webhooks.js
index bc1dff9c6ae..e52294d5ffa 100644
--- a/client/src/components/Masthead/_webhooks.js
+++ b/client/src/components/Masthead/_webhooks.js
@@ -5,8 +5,7 @@ export function loadWebhookMenuItems(items) {
     Webhooks.load({
         type: "masthead",
         callback: function (webhooks) {
-            webhooks.each((model) => {
-                const webhook = model.toJSON();
+            webhooks.forEach((webhook) => {
                 if (webhook.activate) {
                     const obj = {
                         id: webhook.id,
diff --git a/client/src/components/Tool/Buttons/ToolOptionsButton.vue b/client/src/components/Tool/Buttons/ToolOptionsButton.vue
index 4e53cb317e7..ec467c63c9b 100644
--- a/client/src/components/Tool/Buttons/ToolOptionsButton.vue
+++ b/client/src/components/Tool/Buttons/ToolOptionsButton.vue
@@ -6,7 +6,7 @@ import Webhooks from "utils/webhooks";
 import ToolSourceMenuItem from "components/Tool/ToolSourceMenuItem";
 import { FontAwesomeIcon } from "@fortawesome/vue-fontawesome";
 
-const { currentUser: user } = useCurrentUser();
+const { currentUser: user } = useCurrentUser(false, true);
 
 const props = defineProps({
     id: {
@@ -28,9 +28,7 @@ const webhookDetails = ref([]);
 Webhooks.load({
     type: "tool-menu",
     callback: (webhooks) => {
-        webhooks.each((model) => {
-            const webhook = model.toJSON();
-
+        webhooks.forEach((webhook) => {
             if (webhook.activate && webhook.config.function) {
                 webhookDetails.value.push({
                     icon: `fa ${webhook.config.icon}`,
diff --git a/client/src/components/Tool/ToolCard.test.js b/client/src/components/Tool/ToolCard.test.js
index 0ec1a66f60f..0bf54ff9bb2 100644
--- a/client/src/components/Tool/ToolCard.test.js
+++ b/client/src/components/Tool/ToolCard.test.js
@@ -1,5 +1,7 @@
 import { mount } from "@vue/test-utils";
 import { getLocalVue, mockModule } from "tests/jest/helpers";
+import MockAdapter from "axios-mock-adapter";
+import axios from "axios";
 import ToolCard from "./ToolCard";
 import Vuex from "vuex";
 import { userStore } from "store/userStore";
@@ -18,8 +20,12 @@ const createStore = (currentUser) => {
 
 describe("ToolCard", () => {
     let wrapper;
+    let axiosMock;
 
     beforeEach(() => {
+        axiosMock = new MockAdapter(axios);
+        axiosMock.onGet(`/api/webhooks`).reply(200, []);
+
         const store = createStore({
             id: "user.id",
             email: "user.email",
diff --git a/client/src/components/Tool/ToolCard.vue b/client/src/components/Tool/ToolCard.vue
index 9e584cd06d6..dde944c1202 100644
--- a/client/src/components/Tool/ToolCard.vue
+++ b/client/src/components/Tool/ToolCard.vue
@@ -66,7 +66,7 @@ function onSetError(e) {
     errorText.value = e;
 }
 
-const { currentUser: user } = useCurrentUser();
+const { currentUser: user } = useCurrentUser(false, true);
 const hasUser = computed(() => !user.value.isAnonymous);
 
 const versions = computed(() => props.options.versions);
diff --git a/client/src/components/Tool/ToolForm.test.js b/client/src/components/Tool/ToolForm.test.js
index 5f00316645d..df12b6ab34a 100644
--- a/client/src/components/Tool/ToolForm.test.js
+++ b/client/src/components/Tool/ToolForm.test.js
@@ -30,6 +30,7 @@ describe("ToolForm", () => {
             help: "help_text",
         };
         axiosMock.onGet(`/api/tools/tool_id/build?tool_version=version`).reply(200, toolData);
+        axiosMock.onGet(`/api/webhooks`).reply(200, []);
 
         const citations = [];
         axiosMock.onGet(`/api/tools/tool_id/citations`).reply(200, citations);
diff --git a/client/src/components/Tool/ToolSourceMenuItem.vue b/client/src/components/Tool/ToolSourceMenuItem.vue
index d774c2c58eb..d53c332403b 100644
--- a/client/src/components/Tool/ToolSourceMenuItem.vue
+++ b/client/src/components/Tool/ToolSourceMenuItem.vue
@@ -4,8 +4,8 @@ import { useConfig } from "composables/config";
 import { useCurrentUser } from "composables/user";
 import { FontAwesomeIcon } from "@fortawesome/vue-fontawesome";
 
-const { config } = useConfig();
-const { currentUser } = useCurrentUser();
+const { config } = useConfig(true);
+const { currentUser } = useCurrentUser(false, true);
 
 const props = defineProps({
     toolId: {
diff --git a/client/src/components/Workflow/Editor/Forms/FormTool.test.js b/client/src/components/Workflow/Editor/Forms/FormTool.test.js
index 01bdcfb973c..3be5542acac 100644
--- a/client/src/components/Workflow/Editor/Forms/FormTool.test.js
+++ b/client/src/components/Workflow/Editor/Forms/FormTool.test.js
@@ -1,5 +1,7 @@
 import { mount } from "@vue/test-utils";
 import { getLocalVue, mockModule } from "tests/jest/helpers";
+import axios from "axios";
+import MockAdapter from "axios-mock-adapter";
 import FormTool from "./FormTool";
 import MockCurrentUser from "components/providers/MockCurrentUser";
 import MockConfigProvider from "components/providers/MockConfigProvider";
@@ -11,6 +13,9 @@ import { createTestingPinia } from "@pinia/testing";
 const localVue = getLocalVue();
 
 describe("FormTool", () => {
+    const axiosMock = new MockAdapter(axios);
+    axiosMock.onGet(`/api/webhooks`).reply(200, []);
+
     function mountTarget() {
         const store = new Vuex.Store({
             modules: {
diff --git a/client/src/components/Workflow/Editor/Forms/FormTool.vue b/client/src/components/Workflow/Editor/Forms/FormTool.vue
index d56446087be..71f44b9e07e 100644
--- a/client/src/components/Workflow/Editor/Forms/FormTool.vue
+++ b/client/src/components/Workflow/Editor/Forms/FormTool.vue
@@ -1,62 +1,58 @@
 <template>
-    <CurrentUser v-slot="{ user }">
-        <ToolCard
-            v-if="hasData"
-            :id="configForm.id"
-            :user="user"
-            :version="configForm.version"
-            :title="configForm.name"
-            :description="configForm.description"
-            :options="configForm"
-            :message-text="messageText"
-            :message-variant="messageVariant"
-            @onChangeVersion="onChangeVersion"
-            @onUpdateFavorites="onUpdateFavorites">
-            <template v-slot:body>
-                <FormElement
-                    id="__label"
-                    :value="label"
-                    title="Label"
-                    help="Add a step label."
-                    :error="uniqueErrorLabel"
-                    @input="onLabel" />
-                <FormElement
-                    id="__annotation"
-                    :value="annotation"
-                    title="Step Annotation"
-                    :area="true"
-                    help="Add an annotation or notes to this step. Annotations are available when a workflow is viewed."
-                    @input="onAnnotation" />
-                <FormConditional :step="step" v-on="$listeners" />
-                <div class="mt-2 mb-4">
-                    <Heading h2 separator bold size="sm"> Tool Parameters </Heading>
-                    <FormDisplay
-                        :id="id"
-                        :inputs="inputs"
-                        :errors="errors"
-                        text-enable="Set in Advance"
-                        text-disable="Set at Runtime"
-                        :workflow-building-mode="true"
-                        @onChange="onChange" />
-                </div>
-                <div class="mt-2 mb-4">
-                    <Heading h2 separator bold size="sm"> Additional Options </Heading>
-                    <FormSection
-                        :id="stepId"
-                        :node-inputs="stepInputs"
-                        :node-outputs="stepOutputs"
-                        :step="step"
-                        :datatypes="datatypes"
-                        :post-job-actions="postJobActions"
-                        @onChange="onChangePostJobActions" />
-                </div>
-            </template>
-        </ToolCard>
-    </CurrentUser>
+    <ToolCard
+        v-if="hasData"
+        :id="configForm.id"
+        :version="configForm.version"
+        :title="configForm.name"
+        :description="configForm.description"
+        :options="configForm"
+        :message-text="messageText"
+        :message-variant="messageVariant"
+        @onChangeVersion="onChangeVersion"
+        @onUpdateFavorites="onUpdateFavorites">
+        <template v-slot:body>
+            <FormElement
+                id="__label"
+                :value="label"
+                title="Label"
+                help="Add a step label."
+                :error="uniqueErrorLabel"
+                @input="onLabel" />
+            <FormElement
+                id="__annotation"
+                :value="annotation"
+                title="Step Annotation"
+                :area="true"
+                help="Add an annotation or notes to this step. Annotations are available when a workflow is viewed."
+                @input="onAnnotation" />
+            <FormConditional :step="step" v-on="$listeners" />
+            <div class="mt-2 mb-4">
+                <Heading h2 separator bold size="sm"> Tool Parameters </Heading>
+                <FormDisplay
+                    :id="id"
+                    :inputs="inputs"
+                    :errors="errors"
+                    text-enable="Set in Advance"
+                    text-disable="Set at Runtime"
+                    :workflow-building-mode="true"
+                    @onChange="onChange" />
+            </div>
+            <div class="mt-2 mb-4">
+                <Heading h2 separator bold size="sm"> Additional Options </Heading>
+                <FormSection
+                    :id="stepId"
+                    :node-inputs="stepInputs"
+                    :node-outputs="stepOutputs"
+                    :step="step"
+                    :datatypes="datatypes"
+                    :post-job-actions="postJobActions"
+                    @onChange="onChangePostJobActions" />
+            </div>
+        </template>
+    </ToolCard>
 </template>
 
 <script>
-import CurrentUser from "@/components/providers/CurrentUser";
 import FormDisplay from "@/components/Form/FormDisplay.vue";
 import ToolCard from "@/components/Tool/ToolCard.vue";
 import FormSection from "./FormSection.vue";
@@ -71,7 +67,6 @@ import { toRef } from "vue";
 
 export default {
     components: {
-        CurrentUser,
         FormDisplay,
         ToolCard,
         FormElement,
@@ -111,7 +106,7 @@ export default {
     },
     data() {
         return {
-            mainValues: {},
+            mainValues: null,
             messageText: "",
             messageVariant: "success",
         };
@@ -169,7 +164,7 @@ export default {
          * @param { Object } values contains flat key-value pairs `prefixed-name=value`
          */
         onChange(values) {
-            const initialRequest = Object.keys(this.mainValues).length === 0;
+            const initialRequest = this.mainValues === null;
             this.mainValues = values;
             if (!initialRequest) {
                 this.postChanges();
diff --git a/client/src/composables/config.js b/client/src/composables/config.js
index 2e30dc438f1..6cd69fb71be 100644
--- a/client/src/composables/config.js
+++ b/client/src/composables/config.js
@@ -1,7 +1,7 @@
 import { computed, onMounted, inject } from "vue";
 
 /* composable config wrapper */
-export function useConfig() {
+export function useConfig(fetchOnce = false) {
     const store = inject("store");
 
     const config = computed(() => store.getters["config/config"]);
@@ -9,7 +9,9 @@ export function useConfig() {
 
     // Anytime we mount this (for now), make sure to load.
     onMounted(() => {
-        store.dispatch("config/loadConfigs");
+        if (!(fetchOnce && isLoaded)) {
+            store.dispatch("config/loadConfigs");
+        }
     });
 
     return { config, isLoaded };
diff --git a/client/src/composables/user.ts b/client/src/composables/user.ts
index 557b576a3e3..92d864d451c 100644
--- a/client/src/composables/user.ts
+++ b/client/src/composables/user.ts
@@ -6,15 +6,16 @@ import type { Store } from "vuex";
 /**
  * composable user store wrapper
  * @param noFetch when true, the user will not be fetched from the server
+ * @param fetchOnce when true, the user will only be fetched from the server if it is not already in the store
  * @returns currentUser computed
  */
-export function useCurrentUser(noFetch: boolean | Ref<boolean> = false) {
+export function useCurrentUser(noFetch: boolean | Ref<boolean> = false, fetchOnce: boolean | Ref<boolean> = false) {
     // TODO: add store typing
     const store = inject("store") as Store<unknown>;
     const currentUser = computed(() => store.getters["user/currentUser"]);
     const currentFavorites = computed(() => store.getters["user/currentFavorites"]);
     onMounted(() => {
-        if (!unref(noFetch)) {
+        if (!unref(noFetch) && !(Object.keys(currentUser).length > 0) && unref(fetchOnce)) {
             store.dispatch("user/loadUser");
         }
     });
diff --git a/client/src/onload/globalInits/onloadWebhooks.js b/client/src/onload/globalInits/onloadWebhooks.js
index ce74aa64a48..f4dfa6c21b8 100644
--- a/client/src/onload/globalInits/onloadWebhooks.js
+++ b/client/src/onload/globalInits/onloadWebhooks.js
@@ -2,14 +2,11 @@ import Webhooks from "utils/webhooks";
 import Utils from "utils/utils";
 
 export function onloadWebhooks(Galaxy) {
-    console.log("onloadWebhooks");
-
     if (Galaxy.config.enable_webhooks) {
         Webhooks.load({
             type: "onload",
             callback: function (webhooks) {
-                webhooks.each((model) => {
-                    var webhook = model.toJSON();
+                webhooks.forEach((webhook) => {
                     if (webhook.activate && webhook.script) {
                         Utils.appendScriptStyle(webhook);
                     }
diff --git a/client/src/utils/navigation/navigation.yml b/client/src/utils/navigation/navigation.yml
index 7720e0eed86..4157da48d60 100644
--- a/client/src/utils/navigation/navigation.yml
+++ b/client/src/utils/navigation/navigation.yml
@@ -490,6 +490,7 @@ tool_form:
     parameter_checkbox: 'div.ui-form-element[id="form-element-${parameter}"] .ui-switch'
     parameter_input: 'div.ui-form-element[id="form-element-${parameter}"] .ui-input'
     parameter_textarea: 'div.ui-form-element[id="form-element-${parameter}"] textarea'
+    repeat_insert: '[data-description="repeat insert"]'
     reference: '.formatted-reference'
     about: '.tool-footer'
 
diff --git a/client/src/utils/webhooks.js b/client/src/utils/webhooks.js
index 30e0ee69822..1fb9452853a 100644
--- a/client/src/utils/webhooks.js
+++ b/client/src/utils/webhooks.js
@@ -1,12 +1,22 @@
+import axios from "axios";
 import Backbone from "backbone";
 import { getAppRoot } from "onload/loadConfig";
+import { rethrowSimple } from "@/utils/simple-error";
 import Utils from "utils/utils";
 
-const Webhooks = Backbone.Collection.extend({
-    url: function () {
-        return `${getAppRoot()}api/webhooks`;
-    },
-});
+let webhookData = undefined;
+
+async function getWebHookData() {
+    if (webhookData === undefined) {
+        try {
+            const { data } = await axios.get(`${getAppRoot()}api/webhooks`);
+            webhookData = data;
+        } catch (e) {
+            rethrowSimple(e);
+        }
+    }
+    return webhookData;
+}
 
 const WebhookView = Backbone.View.extend({
     el: "#webhook-view",
@@ -18,16 +28,13 @@ const WebhookView = Backbone.View.extend({
         this.$el.attr("tool_id", toolId);
         this.$el.attr("tool_version", toolVersion);
 
-        const webhooks = new Webhooks();
-        webhooks.fetch({
-            success: (data) => {
-                if (options.type) {
-                    data.reset(filterType(data, options.type));
-                }
-                if (data.length > 0) {
-                    this.render(weightedRandomPick(data));
-                }
-            },
+        getWebHookData().then((data) => {
+            if (options.type) {
+                data.reset(filterType(data, options.type));
+            }
+            if (data.length > 0) {
+                this.render(weightedRandomPick(data));
+            }
         });
     },
 
@@ -40,21 +47,18 @@ const WebhookView = Backbone.View.extend({
 });
 
 const load = (options) => {
-    const webhooks = new Webhooks();
-    webhooks.fetch({
-        async: options.async !== undefined ? options.async : true,
-        success: (data) => {
-            if (options.type) {
-                data.reset(filterType(data, options.type));
-            }
-            options.callback(data);
-        },
+    getWebHookData().then((data) => {
+        let filteredData = data;
+        if (options.type) {
+            filteredData = filterType(data, options.type);
+        }
+        options.callback(filteredData);
     });
 };
 
 function filterType(data, type) {
-    return data.models.filter((item) => {
-        const itype = item.get("type");
+    return data.filter((item) => {
+        const itype = item.type;
         if (itype) {
             return itype.indexOf(type) !== -1;
         } else {
diff --git a/lib/galaxy/datatypes/data.py b/lib/galaxy/datatypes/data.py
index c5b75db1d6e..c98e2a73817 100644
--- a/lib/galaxy/datatypes/data.py
+++ b/lib/galaxy/datatypes/data.py
@@ -539,7 +539,7 @@ class Data(metaclass=DataMeta):
                 trans.fill_template_mako(
                     "/dataset/large_file.mako",
                     truncated_data=open(dataset.file_name, "rb").read(max_peek_size),
-                    dataset=dataset,
+                    data=dataset,
                 ),
                 headers,
             )
diff --git a/lib/galaxy/tool_util/xsd/galaxy.xsd b/lib/galaxy/tool_util/xsd/galaxy.xsd
index 4b9e1bad82b..9ba5cfbd890 100644
--- a/lib/galaxy/tool_util/xsd/galaxy.xsd
+++ b/lib/galaxy/tool_util/xsd/galaxy.xsd
@@ -59,6 +59,11 @@ List of behavior changes associated with profile versions:
 
 - Do not strip leading and trailing whitespaces in `from_work_dir` attribute.
 
+### 23.0
+
+- Text parameters that are inferred to be optional (i.e the `optional` tag is not set, but the tool parameter accepts an empty string)
+  are set to `None` for templating in Cheetah. Older tools receive the empty string `""` as the templated value.
+
 ### Examples
 
 A normal tool:
diff --git a/lib/galaxy/tools/evaluation.py b/lib/galaxy/tools/evaluation.py
index 2ae9cd70ca2..e2c400b7e6d 100644
--- a/lib/galaxy/tools/evaluation.py
+++ b/lib/galaxy/tools/evaluation.py
@@ -356,7 +356,9 @@ class ToolEvaluator:
                     input, value, other_values=param_dict, compute_environment=self.compute_environment
                 )
             else:
-                input_values[input.name] = InputValueWrapper(input, value, param_dict)
+                input_values[input.name] = InputValueWrapper(
+                    input, value, param_dict, profile=self.tool and self.tool.profile
+                )
 
         # HACK: only wrap if check_values is not false, this deals with external
         #       tools where the inputs don't even get passed through. These
diff --git a/lib/galaxy/tools/parameters/basic.py b/lib/galaxy/tools/parameters/basic.py
index 235ca27a07f..15d5df5a6e1 100644
--- a/lib/galaxy/tools/parameters/basic.py
+++ b/lib/galaxy/tools/parameters/basic.py
@@ -164,6 +164,7 @@ class ToolParameter(Dictifiable):
         self.hidden = input_source.get_bool("hidden", False)
         self.refresh_on_change = input_source.get_bool("refresh_on_change", False)
         self.optional = input_source.parse_optional()
+        self.optionality_inferred = False
         self.is_dynamic = False
         self.label = input_source.parse_label()
         self.help = input_source.parse_help()
@@ -326,7 +327,24 @@ class SimpleTextToolParameter(ToolParameter):
     def __init__(self, tool, input_source):
         input_source = ensure_input_source(input_source)
         super().__init__(tool, input_source)
-        self.optional = input_source.get_bool("optional", False)
+        optional = input_source.get("optional", None)
+        if optional is not None:
+            optional = string_as_bool(optional)
+        else:
+            # Optionality not explicitly defined, default to False
+            optional = False
+            if self.type == "text":
+                # A text parameter that doesn't raise a validation error on empty string
+                # is considered to be optional
+                try:
+                    for validator in self.validators:
+                        validator.validate("")
+                    optional = True
+                    self.optionality_inferred = True
+                except ValueError:
+                    pass
+        self.optional = optional
+
         if self.optional:
             self.value = None
         else:
@@ -353,7 +371,8 @@ class TextToolParameter(SimpleTextToolParameter):
     >>> p = TextToolParameter(None, XML('<param name="_name" type="text" value="default" />'))
     >>> print(p.name)
     _name
-    >>> assert sorted(p.to_dict(trans).items()) == [('area', False), ('argument', None), ('datalist', []), ('help', ''), ('hidden', False), ('is_dynamic', False), ('label', ''), ('model_class', 'TextToolParameter'), ('name', '_name'), ('optional', False), ('refresh_on_change', False), ('type', 'text'), ('value', u'default')]
+    >>> sorted(p.to_dict(trans).items())
+    [('area', False), ('argument', None), ('datalist', []), ('help', ''), ('hidden', False), ('is_dynamic', False), ('label', ''), ('model_class', 'TextToolParameter'), ('name', '_name'), ('optional', True), ('refresh_on_change', False), ('type', 'text'), ('value', 'default')]
     """
 
     def __init__(self, tool, input_source):
diff --git a/lib/galaxy/tools/parameters/wrapped.py b/lib/galaxy/tools/parameters/wrapped.py
index 71a81c8f245..819b9ac08f6 100644
--- a/lib/galaxy/tools/parameters/wrapped.py
+++ b/lib/galaxy/tools/parameters/wrapped.py
@@ -98,7 +98,7 @@ class WrappedParameters:
                     name=input.name,
                 )
             else:
-                input_values[input.name] = InputValueWrapper(input, value, incoming)
+                input_values[input.name] = InputValueWrapper(input, value, incoming, tool.profile)
 
 
 def make_dict_copy(from_dict):
diff --git a/lib/galaxy/tools/wrappers.py b/lib/galaxy/tools/wrappers.py
index e19a8cb9252..9b9dd56fcb6 100644
--- a/lib/galaxy/tools/wrappers.py
+++ b/lib/galaxy/tools/wrappers.py
@@ -66,7 +66,7 @@ class ToolParameterValueWrapper:
     Base class for object that Wraps a Tool Parameter and Value.
     """
 
-    value: Union[str, List[str]]
+    value: Optional[Union[str, List[str]]]
     input: "ToolParameter"
 
     def __bool__(self) -> bool:
@@ -120,10 +120,20 @@ class InputValueWrapper(ToolParameterValueWrapper):
     def __init__(
         self,
         input: "ToolParameter",
-        value: str,
+        value: Optional[str],
         other_values: Optional[Dict[str, str]] = None,
+        profile: Optional[float] = None,
     ) -> None:
         self.input = input
+        if (
+            value is None
+            and input.type == "text"
+            and input.optional
+            and input.optionality_inferred
+            and (profile is None or profile < 23.0)
+        ):
+            # Tools with old profile versions may treat an optional text parameter as `""`
+            value = ""
         self.value = value
         self._other_values: Dict[str, str] = other_values or {}
 
@@ -236,7 +246,7 @@ class SelectToolParameterWrapper(ToolParameterValueWrapper):
         compute_environment: Optional["ComputeEnvironment"] = None,
     ):
         self.input = input
-        self.value = value
+        self.value: Union[str, List[str]] = value
         self.input.value_label = input.value_to_display_text(value)
         self._other_values = other_values or {}
         self.compute_environment = compute_environment
diff --git a/lib/galaxy_test/selenium/test_workflow_editor.py b/lib/galaxy_test/selenium/test_workflow_editor.py
index b4b3212f6e6..f50d75e87a7 100644
--- a/lib/galaxy_test/selenium/test_workflow_editor.py
+++ b/lib/galaxy_test/selenium/test_workflow_editor.py
@@ -918,6 +918,26 @@ steps:
         output_connector.send_keys(Keys.SPACE)
         assert self.driver.switch_to.active_element.text == "No compatible input found in workflow"
 
+    @selenium_test
+    def test_insert_input_handling(self):
+        self.open_in_workflow_editor(
+            """class: GalaxyWorkflow
+inputs: []
+steps:
+  build_list:
+    tool_id: __BUILD_LIST__
+        """
+        )
+        editor = self.components.workflow_editor
+        node = editor.node._(label="build_list")
+        node.wait_for_and_click()
+        assert not node.has_class("input-terminal")
+        self.components.tool_form.repeat_insert.wait_for_and_click()
+        node.input_terminal(name="datasets_0|input").wait_for_present()
+        self.components.tool_form.repeat_insert.wait_for_and_click()
+        node.input_terminal(name="datasets_1|input").wait_for_present()
+        self.assert_workflow_has_changes_and_save()
+
     @selenium_test
     def test_workflow_output_handling(self):
         self.open_in_workflow_editor(
diff --git a/test/functional/tools/cheetah_casting.xml b/test/functional/tools/cheetah_casting.xml
index ab9c7606158..26cdfc62ea3 100644
--- a/test/functional/tools/cheetah_casting.xml
+++ b/test/functional/tools/cheetah_casting.xml
@@ -3,13 +3,16 @@
         #set $int_val_inc = int($inttest) + 1
         #set $int_flot_val_inc = int($floattest) + 1
         #set $float_val_inc = float($floattest) + 1
-        echo $int_val_inc   >> '$out_file1';
+        #set $text_val = $texttest.strip()
+        echo $int_val_inc >> '$out_file1';
         echo $int_flot_val_inc >> '$out_file1';
         echo $float_val_inc >> '$out_file1';
+        echo $text_val >> '#out_file1'
     </command>
     <inputs>
         <param name="inttest" value="1" type="integer" />
         <param name="floattest" value="1.0" type="float" />
+        <param name="texttest" type="text" />
     </inputs>
     <outputs>
         <data name="out_file1" format="txt" />
@@ -27,4 +30,4 @@
             </output>
         </test>
     </tests>
-</tool>
+</tool>
\ No newline at end of file
diff --git a/test/unit/app/tools/test_parameter_parsing.py b/test/unit/app/tools/test_parameter_parsing.py
index 6c0c01ca28c..abfe41c5c0f 100644
--- a/test/unit/app/tools/test_parameter_parsing.py
+++ b/test/unit/app/tools/test_parameter_parsing.py
@@ -91,7 +91,9 @@ class TestParameterParsing(BaseParameterTestCase):
     def test_parse_optional(self):
         param = self._parameter_for(
             xml="""
-            <param type="text" name="texti" value="mydefault" />
+            <param type="text" name="texti" value="mydefault">
+                <validator type="empty_field" />
+            </param>
         """
         )
         assert param.optional is False