diff --git a/static/js/emailLibrary.js b/static/js/emailLibrary.js
index 8d9758f5d..2c1f8d743 100644
--- a/static/js/emailLibrary.js
+++ b/static/js/emailLibrary.js
@@ -4911,17 +4911,15 @@ async function _openEmailWindow(em, folder) {
           <div class="email-reader-meta-row email-reader-meta-from">
             <strong>From:</strong>
             <span class="recipient-chips">${fromChip}${(data.to || data.cc) ? `<button class="email-reader-meta-toggle" type="button" aria-expanded="false" title="Show recipients"><svg width="11" height="11" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2.5" stroke-linecap="round" stroke-linejoin="round"><polyline points="6 9 12 15 18 9"/></svg></button>` : ''}</span>
-            <div class="email-reader-actions-row email-reader-actions-row-primary">
+            <div class="email-reader-actions-inline">
               <button class="memory-toolbar-btn reader-icon-btn" data-act="reply" title="Reply"><svg width="14" height="14" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round"><polyline points="9 17 4 12 9 7"/><path d="M20 18v-2a4 4 0 0 0-4-4H4"/></svg><span class="reader-btn-label">Reply</span></button>
               ${_hasMultipleRecipients(data) ? `<button class="memory-toolbar-btn reader-icon-btn" data-act="reply-all" title="Reply All"><svg width="14" height="14" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round"><polyline points="7 17 2 12 7 7"/><polyline points="12 17 7 12 12 7"/><path d="M22 18v-2a4 4 0 0 0-4-4H7"/></svg><span class="reader-btn-label">Reply all</span></button>` : ''}
               <button class="memory-toolbar-btn reader-icon-btn" data-act="forward" title="Forward"><svg width="14" height="14" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round"><polyline points="15 17 20 12 15 7"/><path d="M4 18v-2a4 4 0 0 1 4-4h12"/></svg><span class="reader-btn-label">Forward</span></button>
-            </div>
-          </div>
-          <div class="email-reader-actions-row email-reader-actions-row-secondary">
-            <button class="memory-toolbar-btn reader-icon-btn" data-act="summarize" title="Summarize">${_summaryIcon(data)}<span class="reader-btn-label">Summary</span></button>
-            <button class="memory-toolbar-btn reader-icon-btn" data-act="ai-reply" title="${data.cached_ai_reply ? 'AI Reply (cached draft ready)' : 'AI Reply (suggest a draft)'}">${_aiReplyIcon(data)}<span class="reader-btn-label">AI reply</span></button>
-            <div class="email-reader-more-wrap" style="position:relative">
-              <button class="memory-toolbar-btn reader-icon-btn" data-act="more" title="More actions"><svg width="14" height="14" viewBox="0 0 24 24" fill="currentColor"><circle cx="12" cy="5" r="2"/><circle cx="12" cy="12" r="2"/><circle cx="12" cy="19" r="2"/></svg><span class="reader-btn-label">More</span></button>
+              <button class="memory-toolbar-btn reader-icon-btn" data-act="ai-reply" title="${data.cached_ai_reply ? 'AI Reply (cached draft ready)' : 'AI Reply (suggest a draft)'}">${_aiReplyIcon(data)}<span class="reader-btn-label">AI reply</span></button>
+              <button class="memory-toolbar-btn reader-icon-btn" data-act="summarize" title="Summarize">${_summaryIcon(data)}<span class="reader-btn-label">Summary</span></button>
+              <div class="email-reader-more-wrap" style="position:relative">
+                <button class="memory-toolbar-btn reader-icon-btn" data-act="more" title="More actions"><svg width="14" height="14" viewBox="0 0 24 24" fill="currentColor"><circle cx="12" cy="5" r="2"/><circle cx="12" cy="12" r="2"/><circle cx="12" cy="19" r="2"/></svg><span class="reader-btn-label">More</span></button>
+              </div>
             </div>
           </div>
           ${(data.to || data.cc) ? `<div class="email-reader-meta-details" hidden>
diff --git a/static/style.css b/static/style.css
index cb2e6259b..b14c84ae6 100644
--- a/static/style.css
+++ b/static/style.css
@@ -15225,8 +15225,11 @@ body.right-dock-active:not(.email-doc-split-active) .doc-editor-pane {
   background: none;
   padding-left: 0;
 }
-.modal.modal-right-docked .email-reader-meta-row,
-.modal.modal-left-docked .email-reader-meta-row {
+/* Docked modal: From row stays a flex row so the action cluster
+   sits next to From (or wraps below it when truly cramped). Only
+   the To/Cc detail rows get the grid stack. */
+.modal.modal-right-docked .email-reader-meta-row:not(.email-reader-meta-from),
+.modal.modal-left-docked .email-reader-meta-row:not(.email-reader-meta-from) {
   display: grid;
   grid-template-columns: 1fr;
   gap: 2px;
@@ -28044,17 +28047,23 @@ button .spinner-whirlpool {
   gap: 6px;
   min-width: 0;
 }
-/* Primary action row (Reply / Reply-all / Forward) lives INSIDE
-   the From row and gets pushed to the right edge. */
-.email-reader-meta-row.email-reader-meta-from > .email-reader-actions-row-primary {
+/* All action buttons live INSIDE the From row, right-aligned. When
+   there's room (undocked) they sit on the same row as From; when
+   docked or narrow they wrap below it. */
+.email-reader-meta-row.email-reader-meta-from > .email-reader-actions-inline {
   margin-left: auto;
+  display: flex;
+  flex-direction: row;
+  flex-wrap: wrap;
+  align-items: center;
+  justify-content: flex-end;
+  gap: 4px;
   flex-shrink: 0;
 }
-/* Secondary action row (Summary / AI / More) sits below the From
-   row as a sibling, right-aligned. */
-.email-reader-meta > .email-reader-actions-row-secondary {
-  justify-content: flex-end;
-  margin-top: 2px;
+/* From row allows the action cluster to wrap below when narrow. */
+.email-reader-meta-row.email-reader-meta-from {
+  flex-wrap: wrap;
+  row-gap: 2px;
 }
 /* Gmail-style chevron — collapsed view shows only From; the chevron
    reveals the To/Cc details inline below. */
@@ -28165,7 +28174,7 @@ button .spinner-whirlpool {
     background: none;
     padding-left: 0;
   }
-  .email-reader-meta-row {
+  .email-reader-meta-row:not(.email-reader-meta-from) {
     display: grid;
     grid-template-columns: 1fr;
     gap: 2px;