diff --git a/apps/client/src/common/components/input/input/Input.module.scss b/apps/client/src/common/components/input/input/Input.module.scss
index c72eee9a9..bd1fa2563 100644
--- a/apps/client/src/common/components/input/input/Input.module.scss
+++ b/apps/client/src/common/components/input/input/Input.module.scss
@@ -2,7 +2,7 @@
   box-sizing: border-box;
 
   font-size: 1rem;
-  font-weight: 400;
+  font-weight: inherit;
   color: $gray-200;
   border-radius: $component-border-radius-md;
   border: 1px solid transparent;
diff --git a/apps/client/src/common/components/input/textarea/Textarea.module.scss b/apps/client/src/common/components/input/textarea/Textarea.module.scss
index d5b30ca09..cb4cb0454 100644
--- a/apps/client/src/common/components/input/textarea/Textarea.module.scss
+++ b/apps/client/src/common/components/input/textarea/Textarea.module.scss
@@ -4,7 +4,7 @@
 
   display: block;
   font-size: 1rem;
-  font-weight: 400;
+  font-weight: inherit;
   color: $gray-200;
   border-radius: $component-border-radius-md;
   border: 1px solid transparent;
@@ -34,11 +34,13 @@
 
 .subtle {
   background-color: $gray-1200;
+  padding-top: 0.5em;
 }
 
 .ghosted {
   background-color: transparent;
   padding: 0;
+  padding-top: 0.5em;
 }
 
 .fluid {
diff --git a/apps/client/src/common/components/link/external-link/ExternalLink.module.scss b/apps/client/src/common/components/link/external-link/ExternalLink.module.scss
index 9fb22c59a..8b71d6b90 100644
--- a/apps/client/src/common/components/link/external-link/ExternalLink.module.scss
+++ b/apps/client/src/common/components/link/external-link/ExternalLink.module.scss
@@ -7,6 +7,7 @@
   transition-property: color;
   transition-duration: $transition-time-action;
   width: fit-content;
+  text-decoration: none;
 
   &.inline {
     display: inline-flex;
@@ -20,4 +21,4 @@
     outline: none; 
     box-shadow: 0 1px 0 0 currentColor;
   }
-}
+} 
diff --git a/apps/client/src/common/components/modal/Modal.module.scss b/apps/client/src/common/components/modal/Modal.module.scss
index 3138d139e..8c1c43760 100644
--- a/apps/client/src/common/components/modal/Modal.module.scss
+++ b/apps/client/src/common/components/modal/Modal.module.scss
@@ -7,7 +7,7 @@
   padding-inline: 1rem;
   min-width: min(680px, 90vw);
   min-height: min(200px, 10vh);
-  max-width: min(680px, 90vw);
+  max-width: min(800px, 90vw);
 
   background-color: $gray-1250;
   color: $ui-white;
diff --git a/apps/client/src/common/hooks/useEntryAction.ts b/apps/client/src/common/hooks/useEntryAction.ts
index f155c3b20..8bd9c9350 100644
--- a/apps/client/src/common/hooks/useEntryAction.ts
+++ b/apps/client/src/common/hooks/useEntryAction.ts
@@ -15,7 +15,7 @@ import {
 } from 'ontime-types';
 import { dayInMs, generateId, MILLIS_PER_SECOND, parseUserTime, swapEventData } from 'ontime-utils';
 
-import { moveDown, moveUp } from '../../features/rundown/rundown.utils';
+import { moveDown, moveUp, orderEntries } from '../../features/rundown/rundown.utils';
 import { RUNDOWN } from '../api/constants';
 import {
   deleteEntries,
@@ -622,13 +622,22 @@ export const useEntryActions = () => {
    */
   const groupEntries = useCallback(
     async (entryIds: EntryId[]) => {
+      if (entryIds.length === 0) return;
+
       try {
-        await groupEntriesMutation(entryIds);
+        if (entryIds.length === 1) {
+          await groupEntriesMutation(entryIds);
+        } else {
+          const rundown = queryClient.getQueryData<Rundown>(RUNDOWN);
+          if (!rundown) return;
+          const orderedIds = orderEntries(entryIds, rundown.flatOrder);
+          await groupEntriesMutation(orderedIds);
+        }
       } catch (error) {
         logAxiosError('Error grouping entries', error);
       }
     },
-    [groupEntriesMutation],
+    [groupEntriesMutation, queryClient],
   );
 
   /**
diff --git a/apps/client/src/features/app-settings/panel/automations-panel/AutomationSettingsForm.tsx b/apps/client/src/features/app-settings/panel/automations-panel/AutomationSettingsForm.tsx
index 77fdffade..f381e8fe1 100644
--- a/apps/client/src/features/app-settings/panel/automations-panel/AutomationSettingsForm.tsx
+++ b/apps/client/src/features/app-settings/panel/automations-panel/AutomationSettingsForm.tsx
@@ -107,7 +107,9 @@ export default function AutomationSettingsForm(props: AutomationSettingsProps) {
             <Switch
               size='large'
               checked={watch('enabledAutomations')}
-              onCheckedChange={(value: boolean) => setValue('enabledAutomations', value, { shouldDirty: true })}
+              onCheckedChange={(value: boolean) =>
+                setValue('enabledAutomations', value, { shouldDirty: true, shouldValidate: true })
+              }
             />
           </Panel.ListItem>
         </Panel.ListGroup>
@@ -125,7 +127,9 @@ export default function AutomationSettingsForm(props: AutomationSettingsProps) {
             <Switch
               size='large'
               checked={watch('enabledOscIn')}
-              onCheckedChange={(value: boolean) => setValue('enabledOscIn', value, { shouldDirty: true })}
+              onCheckedChange={(value: boolean) =>
+                setValue('enabledOscIn', value, { shouldDirty: true, shouldValidate: true })
+              }
             />
           </Panel.ListItem>
           <Panel.ListItem>
diff --git a/apps/client/src/features/app-settings/panel/automations-panel/TriggerForm.tsx b/apps/client/src/features/app-settings/panel/automations-panel/TriggerForm.tsx
index 02868160a..2a19d94c8 100644
--- a/apps/client/src/features/app-settings/panel/automations-panel/TriggerForm.tsx
+++ b/apps/client/src/features/app-settings/panel/automations-panel/TriggerForm.tsx
@@ -22,8 +22,15 @@ interface TriggerFormProps {
   postSubmit: () => void;
 }
 
-export default function TriggerForm(props: TriggerFormProps) {
-  const { automations, initialId, initialTitle, initialAutomationId, initialTrigger, onCancel, postSubmit } = props;
+export default function TriggerForm({
+  automations,
+  initialId,
+  initialTitle,
+  initialAutomationId,
+  initialTrigger,
+  onCancel,
+  postSubmit,
+}: TriggerFormProps) {
   const {
     handleSubmit,
     register,
@@ -35,8 +42,8 @@ export default function TriggerForm(props: TriggerFormProps) {
   } = useForm<TriggerDTO>({
     defaultValues: {
       title: initialTitle,
-      trigger: initialTrigger,
-      automationId: initialAutomationId,
+      trigger: initialTrigger ?? (cycles[0].value as TimerLifeCycle | undefined),
+      automationId: initialAutomationId ?? automations?.[Object.keys(automations)[0]]?.id,
     },
     resetOptions: {
       keepDirtyValues: true,
diff --git a/apps/client/src/features/app-settings/panel/automations-panel/automationUtils.ts b/apps/client/src/features/app-settings/panel/automations-panel/automationUtils.ts
index 892946389..7184a3d83 100644
--- a/apps/client/src/features/app-settings/panel/automations-panel/automationUtils.ts
+++ b/apps/client/src/features/app-settings/panel/automations-panel/automationUtils.ts
@@ -36,9 +36,9 @@ const staticSelectProperties = [
 ];
 
 const staticNextSelectProperties = [
-  { value: 'eventNow.id', label: 'Next ID' },
-  { value: 'eventNow.title', label: 'Next Title' },
-  { value: 'eventNow.cue', label: 'Next Cue' },
+  { value: 'eventNext.id', label: 'Next ID' },
+  { value: 'eventNext.title', label: 'Next Title' },
+  { value: 'eventNext.cue', label: 'Next Cue' },
 ];
 
 type SelectableField = {
diff --git a/apps/client/src/features/app-settings/panel/manage-panel/sources-panel/preview/PreviewRundown.tsx b/apps/client/src/features/app-settings/panel/manage-panel/sources-panel/preview/PreviewRundown.tsx
index c8456aafc..6efdd4d8d 100644
--- a/apps/client/src/features/app-settings/panel/manage-panel/sources-panel/preview/PreviewRundown.tsx
+++ b/apps/client/src/features/app-settings/panel/manage-panel/sources-panel/preview/PreviewRundown.tsx
@@ -28,7 +28,7 @@ export default function PreviewRundown(props: PreviewRundownProps) {
   const fieldLabels = fieldKeys.map((key) => customFields[key].label);
 
   return (
-    <Panel.Table>
+    <Panel.Table className={style.nowrap}>
       <thead>
         <tr>
           <th>#</th>
diff --git a/apps/client/src/features/control/playback/playback-buttons/PlaybackButtons.tsx b/apps/client/src/features/control/playback/playback-buttons/PlaybackButtons.tsx
index 23efcdc65..059902467 100644
--- a/apps/client/src/features/control/playback/playback-buttons/PlaybackButtons.tsx
+++ b/apps/client/src/features/control/playback/playback-buttons/PlaybackButtons.tsx
@@ -1,5 +1,5 @@
 import { useMemo } from 'react';
-import { IoPause, IoPlay, IoPlaySkipBack, IoPlaySkipForward, IoReload, IoStop, IoTime } from 'react-icons/io5';
+import { IoPause, IoPlay, IoPlaySkipBack, IoPlaySkipForward, IoReload, IoStop } from 'react-icons/io5';
 import { Playback, TimerPhase } from 'ontime-types';
 import { validatePlayback } from 'ontime-utils';
 
@@ -73,7 +73,7 @@ export default function PlaybackButtons(props: PlaybackButtonsProps) {
       </div>
       <div className={style.extra}>
         <TapButton onClick={setPlayback.roll} disabled={disableRoll} theme={Playback.Roll} active={isRolling}>
-          <IoTime />
+          Roll
         </TapButton>
         <TapButton onClick={setPlayback.reload} disabled={disableReload}>
           <IoReload className={style.invertX} />
diff --git a/apps/client/src/features/rundown/Rundown.tsx b/apps/client/src/features/rundown/Rundown.tsx
index 333875144..3ccada4bc 100644
--- a/apps/client/src/features/rundown/Rundown.tsx
+++ b/apps/client/src/features/rundown/Rundown.tsx
@@ -298,8 +298,15 @@ export default function Rundown({ data }: RundownProps) {
       return;
     }
     const index = order.findIndex((id) => id === featureData.selectedEventId);
+    // @ts-expect-error -- but we safely check if the parent property exists
+    const maybeParent = entries[featureData.selectedEventId]?.parent;
+    if (maybeParent) {
+      // open the group
+      setCollapsedGroups((prev) => [...prev].filter((id) => id !== maybeParent));
+    }
+
     setSelectedEvents({ id: featureData.selectedEventId, selectMode: 'click', index });
-  }, [editorMode, featureData.selectedEventId, order, setSelectedEvents]);
+  }, [editorMode, entries, featureData.selectedEventId, order, setCollapsedGroups, setSelectedEvents]);
 
   /**
    * On drag end, we reorder the events
diff --git a/apps/client/src/features/rundown/__tests__/rundown.utils.test.ts b/apps/client/src/features/rundown/__tests__/rundown.utils.test.ts
index 7a61b9e25..047a05d51 100644
--- a/apps/client/src/features/rundown/__tests__/rundown.utils.test.ts
+++ b/apps/client/src/features/rundown/__tests__/rundown.utils.test.ts
@@ -1,6 +1,6 @@
 import { EntryId, OntimeBlock, OntimeDelay, OntimeEvent, RundownEntries, SupportedEntry } from 'ontime-types';
 
-import { makeRundownMetadata, makeSortableList, moveDown, moveUp } from '../rundown.utils';
+import { makeRundownMetadata, makeSortableList, moveDown, moveUp, orderEntries } from '../rundown.utils';
 
 describe('makeRundownMetadata()', () => {
   it('processes nested rundown data', () => {
@@ -339,7 +339,6 @@ describe('makeSortableList()', () => {
   });
 });
 
-
 describe('moveUp()', () => {
   const rundown = {
     entries: {
@@ -535,3 +534,40 @@ describe('moveDown()', () => {
     });
   });
 });
+
+describe('orderEntries()', () => {
+  it('should return an empty array when both inputs are empty', () => {
+    const unorderedArray: string[] = [];
+    const flatOrder: string[] = [];
+    const result = orderEntries(unorderedArray, flatOrder);
+    expect(result).toEqual([]);
+  });
+
+  it('should return an ordered array based on flatOrder', () => {
+    const unorderedArray = ['b', 'a', 'c'];
+    const flatOrder = ['a', 'b', 'c'];
+    const result = orderEntries(unorderedArray, flatOrder);
+    expect(result).toEqual(['a', 'b', 'c']);
+  });
+
+  it('should ignore elements in unorderedArray not present in flatOrder', () => {
+    const unorderedArray = ['b', 'a', 'c', 'd'];
+    const flatOrder = ['a', 'b', 'c'];
+    const result = orderEntries(unorderedArray, flatOrder);
+    expect(result).toEqual(['a', 'b', 'c']);
+  });
+
+  it('should handle cases where flatOrder has elements not in unorderedArray', () => {
+    const unorderedArray = ['b', 'a'];
+    const flatOrder = ['a', 'b', 'c'];
+    const result = orderEntries(unorderedArray, flatOrder);
+    expect(result).toEqual(['a', 'b']);
+  });
+
+  it('should return an empty array if unorderedArray has no matching elements in flatOrder', () => {
+    const unorderedArray = ['x', 'y', 'z'];
+    const flatOrder = ['a', 'b', 'c'];
+    const result = orderEntries(unorderedArray, flatOrder);
+    expect(result).toEqual([]);
+  });
+});
diff --git a/apps/client/src/features/rundown/rundown-block/RundownBlock.tsx b/apps/client/src/features/rundown/rundown-block/RundownBlock.tsx
index 08a064f2d..21d6bdb41 100644
--- a/apps/client/src/features/rundown/rundown-block/RundownBlock.tsx
+++ b/apps/client/src/features/rundown/rundown-block/RundownBlock.tsx
@@ -43,7 +43,6 @@ export default function RundownBlock({ data, hasCursor, collapsed, onCollapse }:
     },
     {
       type: 'item',
-
       label: 'Ungroup',
       icon: IoFolderOpenOutline,
       onClick: () => ungroup(data.id),
@@ -55,7 +54,6 @@ export default function RundownBlock({ data, hasCursor, collapsed, onCollapse }:
       label: 'Delete Group',
       icon: IoTrash,
       onClick: () => deleteEntry([data.id]),
-      disabled: true,
     },
   ]);
 
diff --git a/apps/client/src/features/rundown/rundown-event/RundownEvent.module.scss b/apps/client/src/features/rundown/rundown-event/RundownEvent.module.scss
index dac3c67d8..0b96b901f 100644
--- a/apps/client/src/features/rundown/rundown-event/RundownEvent.module.scss
+++ b/apps/client/src/features/rundown/rundown-event/RundownEvent.module.scss
@@ -94,7 +94,7 @@ $skip-opacity: 0.2;
   cursor: pointer;
 
   background-color: $gray-1050; // to override inline
-  color: $section-white;
+  color: $section-white; // to override inline
   font-size: 1rem;
   border-radius: 3px 0 0 3px;
 
diff --git a/apps/client/src/features/rundown/rundown-milestone/RundownMilestone.module.scss b/apps/client/src/features/rundown/rundown-milestone/RundownMilestone.module.scss
index c923da758..048c921fd 100644
--- a/apps/client/src/features/rundown/rundown-milestone/RundownMilestone.module.scss
+++ b/apps/client/src/features/rundown/rundown-milestone/RundownMilestone.module.scss
@@ -6,7 +6,8 @@
   margin-left: calc(2rem + 1px); // binder + border
   margin-block: 0.125rem;
   padding-right: 0.25rem;
-  background-color: color-mix(in srgb, var(--user-bg, $block-bg) 15%, transparent 85%);
+  background-color: $gray-1050; // to override inline
+  color: $section-white; // to override inline
 
   display: grid;
   grid-template-columns: 2rem 8rem 1fr auto;
@@ -23,7 +24,8 @@
   height: 100%;
   display: grid;
   place-content: center;
-  background-color: var(--user-bg, $block-bg);
+  background-color: $gray-1050; // to override inline
+  color: $section-white; // to override inline
 }
 
 .drag {
diff --git a/apps/client/src/features/rundown/rundown-milestone/RundownMilestone.tsx b/apps/client/src/features/rundown/rundown-milestone/RundownMilestone.tsx
index 3c02d6e27..6caeae62c 100644
--- a/apps/client/src/features/rundown/rundown-milestone/RundownMilestone.tsx
+++ b/apps/client/src/features/rundown/rundown-milestone/RundownMilestone.tsx
@@ -76,17 +76,11 @@ export default function RundownMilestone({ colour, cue, entryId, hasCursor, titl
       className={cx([style.milestone, hasCursor ? style.hasCursor : null])}
       ref={setNodeRef}
       onClick={handleFocusClick}
-      style={{ ...dragStyle, '--user-bg': colour }}
+      style={dragStyle}
       data-testid='rundown-milestone'
     >
-      <div className={style.binder}>
-        <span
-          className={style.drag}
-          style={{ ...binderColours }}
-          ref={handleRef}
-          {...dragAttributes}
-          {...dragListeners}
-        >
+      <div className={style.binder} style={{ ...binderColours }}>
+        <span className={style.drag} ref={handleRef} {...dragAttributes} {...dragListeners}>
           <IoReorderTwo />
         </span>
       </div>
diff --git a/apps/client/src/features/rundown/rundown.utils.ts b/apps/client/src/features/rundown/rundown.utils.ts
index 4066b85ed..368f400fb 100644
--- a/apps/client/src/features/rundown/rundown.utils.ts
+++ b/apps/client/src/features/rundown/rundown.utils.ts
@@ -306,3 +306,17 @@ export function moveDown(
   // default - swap positions with next entry
   return { destinationId: nextEntryId, order: 'after' };
 }
+
+/**
+ * Reorders unorderedArray to match the flatOrder entries
+ * Useful for operations that convert selections (out of order) to rundown
+ */
+export function orderEntries(unorderedArray: EntryId[], flatOrder: EntryId[]): EntryId[] {
+  const orderedArray: EntryId[] = [];
+  for (const id of flatOrder) {
+    if (unorderedArray.includes(id)) {
+      orderedArray.push(id);
+    }
+  }
+  return orderedArray;
+}
diff --git a/apps/client/src/views/cuesheet/cuesheet-table/cuesheet-table-elements/BlockRow.module.scss b/apps/client/src/views/cuesheet/cuesheet-table/cuesheet-table-elements/BlockRow.module.scss
index b707b8142..a75b8937c 100644
--- a/apps/client/src/views/cuesheet/cuesheet-table/cuesheet-table-elements/BlockRow.module.scss
+++ b/apps/client/src/views/cuesheet/cuesheet-table/cuesheet-table-elements/BlockRow.module.scss
@@ -14,6 +14,8 @@
   position: relative;
   line-height: 1em;
 
+  font-weight: bold;
+
   td {
     min-height: 3.5rem;
     padding-top: 0.75rem !important; // fighting styles from cuesheet-table
diff --git a/apps/client/src/views/cuesheet/cuesheet-table/cuesheet-table-elements/MilestoneRow.module.scss b/apps/client/src/views/cuesheet/cuesheet-table/cuesheet-table-elements/MilestoneRow.module.scss
index 6298c5edf..c9867f8e3 100644
--- a/apps/client/src/views/cuesheet/cuesheet-table/cuesheet-table-elements/MilestoneRow.module.scss
+++ b/apps/client/src/views/cuesheet/cuesheet-table/cuesheet-table-elements/MilestoneRow.module.scss
@@ -4,6 +4,8 @@
   background: color-mix(in srgb, transparent 92%, var(--user-bg, $gray-500) 8%);
   border-left: 4px solid var(--user-bg, $gray-500);
 
+  font-style: italic;
+
   &:hover {
     outline: 1px solid $blue-500;
     outline-offset: -1px;
diff --git a/apps/client/src/views/cuesheet/cuesheet-table/cuesheet-table-elements/TextLikeInput.module.scss b/apps/client/src/views/cuesheet/cuesheet-table/cuesheet-table-elements/TextLikeInput.module.scss
index ae189f55a..cdba636fc 100644
--- a/apps/client/src/views/cuesheet/cuesheet-table/cuesheet-table-elements/TextLikeInput.module.scss
+++ b/apps/client/src/views/cuesheet/cuesheet-table/cuesheet-table-elements/TextLikeInput.module.scss
@@ -3,6 +3,7 @@
   height: 2rem;
   background-color: transparent;
   border-radius: $component-border-radius-md;
+  text-wrap: nowrap;
 
   display: flex;
   align-items: center;
diff --git a/apps/server/src/api-data/rundown/__tests__/rundown.dao.test.ts b/apps/server/src/api-data/rundown/__tests__/rundown.dao.test.ts
index 3c0b17e92..99a9c737b 100644
--- a/apps/server/src/api-data/rundown/__tests__/rundown.dao.test.ts
+++ b/apps/server/src/api-data/rundown/__tests__/rundown.dao.test.ts
@@ -1620,7 +1620,7 @@ describe('rundownMutation.clone()', () => {
 });
 
 describe('rundownMutation.group()', () => {
-  it('groups a list of existing events into a new block', () => {
+  it('groups a list of existing events into a new group entry', () => {
     const rundown = makeRundown({
       order: ['1', '2', '3'],
       entries: {
diff --git a/apps/server/src/api-data/rundown/rundown.dao.ts b/apps/server/src/api-data/rundown/rundown.dao.ts
index 96e10aa02..1f691fc96 100644
--- a/apps/server/src/api-data/rundown/rundown.dao.ts
+++ b/apps/server/src/api-data/rundown/rundown.dao.ts
@@ -490,9 +490,9 @@ function clone(rundown: Rundown, entry: OntimeEntry): OntimeEntry {
 }
 
 /**
- * Groups a list of entries into a block
+ * Groups a list of entries
  * It ensures that the entries get reassigned parent and the block gets a list of events
- * The block will be created at the index of the first event in the order, not at the lowest index
+ * The group will be created at the index of the first event in the order, not at the lowest index
  * Mutates the given rundown
  */
 function group(rundown: Rundown, entryIds: EntryId[]): OntimeBlock {