From 789329c9c296ec302d4e48a6e6afea32fd0a10b5 Mon Sep 17 00:00:00 2001
From: kenny lopez <klopez4212@gmail.com>
Date: Tue, 18 Aug 2026 16:47:12 +0100
Subject: [PATCH] Polish channel rows and split message media

Signed-off-by: kenny lopez <klopez4212@gmail.com>
---
 .../lib/outgoingMessageParts.test.mjs         |  86 ++++++++
 .../messages/lib/outgoingMessageParts.ts      |  43 ++--
 .../messages/ui/useMentionSendFlow.ts         |  52 ++++-
 .../features/sidebar/ui/SidebarSection.tsx    |  10 +-
 desktop/src/shared/lib/linkPreview.test.mjs   |  45 +++++
 desktop/src/shared/lib/linkPreview.ts         | 183 ++++++++++++++++--
 .../src/shared/styles/globals/markdown.css    |  10 +-
 desktop/tests/e2e/channels.spec.ts            |  12 +-
 desktop/tests/e2e/file-attachment.spec.ts     |   1 +
 .../e2e/message-feedback-snapshots.spec.ts    |  49 +++++
 desktop/tests/e2e/messaging.spec.ts           |  85 ++++++++
 11 files changed, 527 insertions(+), 49 deletions(-)

diff --git a/desktop/src/features/messages/lib/outgoingMessageParts.test.mjs b/desktop/src/features/messages/lib/outgoingMessageParts.test.mjs
index 108f36c049..b51c8e8ab4 100644
--- a/desktop/src/features/messages/lib/outgoingMessageParts.test.mjs
+++ b/desktop/src/features/messages/lib/outgoingMessageParts.test.mjs
@@ -51,3 +51,89 @@ test("text-only submissions remain one text event", () => {
     { content: "hello", kind: "text", outgoingTags: undefined },
   ]);
 });
+
+test("mixed link submissions put the link preview before remaining text", () => {
+  const previewTag = [
+    "link-preview",
+    "snapshot",
+    "1",
+    "https://example.com/launch",
+  ];
+  const emojiTag = ["emoji", "ship", "https://relay.example/ship.png"];
+  const parts = buildOutgoingMessageParts({
+    body: "Launch notes https://example.com/launch are ready :ship:",
+    media: [],
+    nowSeconds: 100,
+    textTags: [previewTag, emojiTag],
+  });
+
+  assert.deepEqual(parts, [
+    {
+      content: "https://example.com/launch",
+      createdAt: 99,
+      kind: "link",
+      outgoingTags: [previewTag],
+    },
+    {
+      content: "Launch notes are ready :ship:",
+      kind: "text",
+      outgoingTags: [emojiTag],
+    },
+  ]);
+});
+
+test("attachment, link, and prose events keep media-first ordering", () => {
+  const parts = buildOutgoingMessageParts({
+    body: "Context for https://example.com/launch",
+    media: [image],
+    nowSeconds: 100,
+  });
+
+  assert.equal(parts.length, 3);
+  assert.equal(parts[0].kind, "media");
+  assert.equal(parts[0].createdAt, 98);
+  assert.equal(parts[1].kind, "link");
+  assert.equal(parts[1].createdAt, 99);
+  assert.equal(parts[2].kind, "text");
+  assert.equal(parts[2].createdAt, undefined);
+});
+
+test("link-only submissions remain one link event", () => {
+  assert.deepEqual(
+    buildOutgoingMessageParts({
+      body: "https://example.com/launch",
+      media: [],
+      nowSeconds: 100,
+    }),
+    [
+      {
+        content: "https://example.com/launch",
+        kind: "link",
+        outgoingTags: undefined,
+      },
+    ],
+  );
+});
+
+test("markdown link labels remain readable in the prose event", () => {
+  assert.deepEqual(
+    buildOutgoingMessageParts({
+      body: "Please review [the launch plan](https://example.com/launch).",
+      media: [],
+      nowSeconds: 100,
+    }),
+    [
+      {
+        content: "https://example.com/launch",
+        createdAt: 99,
+        kind: "link",
+        outgoingTags: undefined,
+      },
+      {
+        content: "Please review the launch plan.",
+        kind: "text",
+        outgoingTags: undefined,
+      },
+    ],
+  );
+});
diff --git a/desktop/src/features/messages/lib/outgoingMessageParts.ts b/desktop/src/features/messages/lib/outgoingMessageParts.ts
index 8f10db5720..ddf4a0dc15 100644
--- a/desktop/src/features/messages/lib/outgoingMessageParts.ts
+++ b/desktop/src/features/messages/lib/outgoingMessageParts.ts
@@ -1,15 +1,17 @@
 import { buildOutgoingMessage, type ImetaMedia } from "./imetaMediaMarkdown";
+import { splitOutgoingLinkContent } from "@/shared/lib/linkPreview";
 
 export type OutgoingMessagePart = {
   content: string;
   createdAt?: number;
-  kind: "media" | "text";
+  kind: "link" | "media" | "text";
   outgoingTags: string[][] | undefined;
 };
 
 /**
  * Build the ordered events for one composer submission. Attachments remain
- * together in a media-only event and precede any authored text event.
+ * together in a media-only event, authored links move to a link-only event,
+ * and both precede any remaining authored text event.
  */
 export function buildOutgoingMessageParts({
   body,
@@ -25,28 +27,45 @@ export function buildOutgoingMessageParts({
   textTags?: string[][];
 }): OutgoingMessagePart[] {
   const parts: OutgoingMessagePart[] = [];
-  const hasText = body.trim().length > 0;
+  const { linkContent, textContent } = splitOutgoingLinkContent(body);
+  const linkTags = textTags.filter((tag) => tag[0] === "link-preview");
+  const remainingTextTags = textTags.filter((tag) => tag[0] !== "link-preview");
 
   if (media.length > 0) {
     const mediaMessage = buildOutgoingMessage("", media, spoileredMediaUrls);
     parts.push({
       content: mediaMessage.content,
-      // Relay events sort by whole-second timestamps and then event id. Give
-      // the media half of a mixed submission the immediately preceding second
-      // so every client renders it first without delaying either network send.
-      createdAt: hasText ? Math.max(0, nowSeconds - 1) : undefined,
       kind: "media",
       outgoingTags: mediaMessage.mediaTags,
     });
   }
 
-  if (hasText) {
+  if (linkContent) {
     parts.push({
-      content: body,
-      kind: "text",
-      outgoingTags: textTags.length > 0 ? textTags : undefined,
+      content: linkContent,
+      kind: "link",
+      outgoingTags: linkTags.length > 0 ? linkTags : undefined,
     });
   }
 
-  return parts;
+  if (textContent) {
+    parts.push({
+      content: textContent,
+      kind: "text",
+      outgoingTags:
+        remainingTextTags.length > 0 ? remainingTextTags : undefined,
+    });
+  }
+
+  // Relay events sort by whole-second timestamps and then event id. Backdate
+  // every part except the final one by one additional second so attachment →
+  // link → prose order is stable without delaying any network send.
+  return parts.map((part, index) =>
+    index < parts.length - 1
+      ? {
+          ...part,
+          createdAt: Math.max(0, nowSeconds - (parts.length - 1 - index)),
+        }
+      : part,
+  );
 }
diff --git a/desktop/src/features/messages/ui/useMentionSendFlow.ts b/desktop/src/features/messages/ui/useMentionSendFlow.ts
index d7a004c1a8..68b4ae55a3 100644
--- a/desktop/src/features/messages/ui/useMentionSendFlow.ts
+++ b/desktop/src/features/messages/ui/useMentionSendFlow.ts
@@ -493,7 +493,15 @@ export function useMentionSendFlow({
           );
         const send = onSendRef.current;
         let mediaMessageSent = false;
-        const persistCanceledDraft = (withoutMedia = false) => {
+        let linkMessageSent = false;
+        let remainingTextContent = draft.savedContent;
+        const persistCanceledDraft = ({
+          content = draft.savedContent,
+          withoutMedia = false,
+        }: {
+          content?: string;
+          withoutMedia?: boolean;
+        } = {}) => {
           if (isSendCancelled() || !draft.recoveryDraftKey) return;
           const existing = drafts.loadDraft(draft.recoveryDraftKey);
           if (
@@ -510,16 +518,22 @@ export function useMentionSendFlow({
           }
           drafts.persistDraft(
             draft.recoveryDraftKey,
-            draft.savedContent,
+            content,
             draft.capturedChannelId ?? draft.recoveryDraftKey,
             withoutMedia ? [] : draft.savedImeta,
             withoutMedia ? [] : [...draft.savedSpoileredAttachmentUrls],
             draft.savedMentionRefs,
           );
         };
-        const restoreComposerAfterFailure = (withoutMedia = false) => {
+        const restoreComposerAfterFailure = ({
+          content = draft.savedContent,
+          withoutMedia = false,
+        }: {
+          content?: string;
+          withoutMedia?: boolean;
+        } = {}) => {
           if (isSendCancelled()) return;
-          persistCanceledDraft(withoutMedia);
+          persistCanceledDraft({ content, withoutMedia });
           const canRestoreCurrentComposer =
             isMountedRef.current &&
             (draft.capturedChannelId === channelIdRef.current ||
@@ -535,9 +549,9 @@ export function useMentionSendFlow({
           if (!canRestoreCurrentComposer) {
             return;
           }
-          setContent(draft.savedContent);
-          contentRef.current = draft.savedContent;
-          richText.setContent(draft.savedContent);
+          setContent(content);
+          contentRef.current = content;
+          richText.setContent(content);
           setPendingImeta(withoutMedia ? [] : draft.savedImeta);
           restoreQueuedAttachments(withoutMedia ? [] : draft.queuedAttachments);
           mentions.restoreDraftMentionRefs(draft.savedMentionRefs);
@@ -564,6 +578,8 @@ export function useMentionSendFlow({
             ]),
             textTags,
           });
+          remainingTextContent =
+            parts.find((part) => part.kind === "text")?.content ?? "";
           const revalidatedMentionPubkeys =
             await mentions.revalidateMentionPubkeys(mentionPubkeys);
           if (signal?.aborted || isSendCancelled()) return;
@@ -583,6 +599,7 @@ export function useMentionSendFlow({
               draft.preparedLinkPreviews != null,
             );
             if (part.kind === "media") mediaMessageSent = true;
+            if (part.kind === "link") linkMessageSent = true;
             if (signal?.aborted || isSendCancelled()) return;
           }
           if (signal?.aborted || isSendCancelled()) return;
@@ -610,7 +627,12 @@ export function useMentionSendFlow({
               try {
                 await finishSend(uploaded, signal);
               } catch {
-                restoreComposerAfterFailure(mediaMessageSent);
+                restoreComposerAfterFailure({
+                  content: linkMessageSent
+                    ? remainingTextContent
+                    : draft.savedContent,
+                  withoutMedia: mediaMessageSent,
+                });
               }
             },
             onError: (error) => {
@@ -620,7 +642,12 @@ export function useMentionSendFlow({
               );
             },
             onCancel: () => {
-              restoreComposerAfterFailure(mediaMessageSent);
+              restoreComposerAfterFailure({
+                content: linkMessageSent
+                  ? remainingTextContent
+                  : draft.savedContent,
+                withoutMedia: mediaMessageSent,
+              });
             },
           });
           if (!uploadStarted) {
@@ -640,7 +667,12 @@ export function useMentionSendFlow({
           try {
             await finishSend([]);
           } catch {
-            restoreComposerAfterFailure(mediaMessageSent);
+            restoreComposerAfterFailure({
+              content: linkMessageSent
+                ? remainingTextContent
+                : draft.savedContent,
+              withoutMedia: mediaMessageSent,
+            });
           }
         }
       } finally {
diff --git a/desktop/src/features/sidebar/ui/SidebarSection.tsx b/desktop/src/features/sidebar/ui/SidebarSection.tsx
index 9823ced175..a93d97e18d 100644
--- a/desktop/src/features/sidebar/ui/SidebarSection.tsx
+++ b/desktop/src/features/sidebar/ui/SidebarSection.tsx
@@ -306,7 +306,8 @@ export function ChannelMenuButton({
     <SidebarMenuButton
       className={cn(
         "data-[active=true]:font-normal",
-        !isDm && "h-12 gap-2 p-1 pr-2 group-data-[collapsible=icon]:!p-0",
+        !isDm &&
+          "h-12 gap-2 rounded-2xl p-1 pr-2 group-data-[collapsible=icon]:!p-0 group-data-[collapsible=icon]:rounded-md",
         isActive
           ? "group-hover/menu-item:bg-sidebar-active group-hover/menu-item:text-sidebar-active-foreground"
           : "group-hover/menu-item:bg-sidebar-accent group-hover/menu-item:text-sidebar-foreground",
@@ -331,14 +332,13 @@ export function ChannelMenuButton({
         <span
           aria-hidden="true"
           className={cn(
-            "flex size-10 shrink-0 items-center justify-center rounded-xl bg-sidebar-border/55 text-sidebar-foreground/65 transition-colors group-data-[collapsible=icon]:size-8 group-data-[collapsible=icon]:rounded-md group-data-[collapsible=icon]:bg-transparent",
-            isActive &&
-              "bg-sidebar-active-foreground/10 text-sidebar-active-foreground",
+            "flex size-10 shrink-0 items-center justify-center rounded-xl bg-background text-sidebar-foreground/65 transition-colors group-data-[collapsible=icon]:size-8 group-data-[collapsible=icon]:rounded-md group-data-[collapsible=icon]:bg-transparent",
+            isActive && "text-sidebar-active-foreground",
             inactiveContentOpacity,
           )}
           data-testid={`channel-icon-container-${channel.name}`}
         >
-          <SidebarChannelIcon channel={channel} className="size-6" />
+          <SidebarChannelIcon channel={channel} className="size-4" />
         </span>
       )}
       {isDm ? (
diff --git a/desktop/src/shared/lib/linkPreview.test.mjs b/desktop/src/shared/lib/linkPreview.test.mjs
index d0f9adfba4..367ba97fff 100644
--- a/desktop/src/shared/lib/linkPreview.test.mjs
+++ b/desktop/src/shared/lib/linkPreview.test.mjs
@@ -5,6 +5,7 @@ import {
   extractSupportedLinkPreviews,
   isSupportedLinkAutolinkLabel,
   parseSupportedLinkPreview,
+  splitOutgoingLinkContent,
 } from "./linkPreview.ts";
 
 test("parseSupportedLinkPreview parses GitHub pull request URLs", () => {
@@ -559,3 +560,47 @@ test("extractSupportedLinkPreviews finds generic links and preserves exclusions"
     ],
   );
 });
+
+test("splitOutgoingLinkContent separates visible links from prose", () => {
+  assert.deepEqual(
+    splitOutgoingLinkContent(
+      "Review [the plan](https://example.com/plan), then share <https://example.com/launch>.",
+    ),
+    {
+      linkContent: "https://example.com/plan\n<https://example.com/launch>",
+      textContent: "Review the plan, then share.",
+    },
+  );
+});
+
+test("splitOutgoingLinkContent includes links without rich previews", () => {
+  assert.deepEqual(
+    splitOutgoingLinkContent(
+      "Source https://github.com/block/buzz/blob/main/README.md and http://example.com/docs",
+    ),
+    {
+      linkContent:
+        "https://github.com/block/buzz/blob/main/README.md\nhttp://example.com/docs",
+      textContent: "Source and",
+    },
+  );
+});
+
+test("splitOutgoingLinkContent preserves hidden and image links", () => {
+  const content = [
+    "Visible https://example.com/visible",
+    "`https://example.com/code`",
+    "||https://example.com/spoiler||",
+    "![image](https://example.com/image.png)",
+  ].join("\n");
+
+  assert.deepEqual(splitOutgoingLinkContent(content), {
+    linkContent: "https://example.com/visible",
+    textContent: [
+      "Visible",
+      "`https://example.com/code`",
+      "||https://example.com/spoiler||",
+      "![image](https://example.com/image.png)",
+    ].join("\n"),
+  });
+});
diff --git a/desktop/src/shared/lib/linkPreview.ts b/desktop/src/shared/lib/linkPreview.ts
index 22354837f7..c29b7330d5 100644
--- a/desktop/src/shared/lib/linkPreview.ts
+++ b/desktop/src/shared/lib/linkPreview.ts
@@ -52,6 +52,10 @@ const SUPPORTED_URL_RE =
   /(^|[\s([{<>"'])(https:\/\/[^\s<>"'\]]+|https?:\/\/[^\s<>"'\]]+\/git\/[a-f0-9]{64}\/[^\s<>"'\]]+|buzz:\/\/(?:pr|issue|repo|project)\?[^\s<>"'\]]+|(?:(?:www\.)?github\.com|(?:www\.)?linear\.app|drive\.google\.com|docs\.google\.com)\/[^\s<>"'\]]+)/gi;
 const MARKDOWN_SUPPORTED_LINK_RE =
   /!?\[([^\]\n]+)\]\((https:\/\/[^)\s<>"']+|https?:\/\/[^)\s<>"']+\/git\/[a-f0-9]{64}\/[^)\s<>"']+|buzz:\/\/(?:pr|issue|repo|project)\?[^)\s<>"']+|(?:(?:www\.)?github\.com|(?:www\.)?linear\.app|drive\.google\.com|docs\.google\.com)\/[^)\s<>"']+)\)/gi;
+const OUTGOING_URL_RE =
+  /(^|[\s([{<>"'])(https?:\/\/[^\s<>"'\]]+|buzz:\/\/(?:pr|issue|repo|project)\?[^\s<>"'\]]+)/gi;
+const MARKDOWN_OUTGOING_LINK_RE =
+  /!?\[([^\]\n]+)\]\((https?:\/\/[^)\s<>"']+|buzz:\/\/(?:pr|issue|repo|project)\?[^)\s<>"']+)\)/gi;
 const MAX_PREVIEWS = 8;
 
 type HiddenRange = {
@@ -124,12 +128,17 @@ function collectCodeRanges(content: string): HiddenRange[] {
 function collectMarkdownImageLinkRanges(content: string): HiddenRange[] {
   const ranges: HiddenRange[] = [];
 
-  for (const match of content.matchAll(MARKDOWN_SUPPORTED_LINK_RE)) {
-    if (!match[0]?.startsWith("!")) continue;
-    ranges.push({
-      start: match.index ?? 0,
-      end: (match.index ?? 0) + match[0].length,
-    });
+  for (const expression of [
+    MARKDOWN_SUPPORTED_LINK_RE,
+    MARKDOWN_OUTGOING_LINK_RE,
+  ]) {
+    for (const match of content.matchAll(expression)) {
+      if (!match[0]?.startsWith("!")) continue;
+      ranges.push({
+        start: match.index ?? 0,
+        end: (match.index ?? 0) + match[0].length,
+      });
+    }
   }
 
   return ranges;
@@ -618,30 +627,31 @@ function withTitle(
 }
 
 type LinkPreviewCandidate = {
+  end: number;
   href: string;
   index: number;
   label?: string;
+  linkSource: string;
   order: number;
+  replacement: string;
 };
 
-/** Extract supported link previews from message text, preserving first-seen order. */
-export function extractSupportedLinkPreviews(
-  content: string,
-  activeRelayOrigin?: string | null,
-): SupportedLinkPreview[] {
-  const previews: SupportedLinkPreview[] = [];
-  const seen = new Set<string>();
+function collectLinkPreviewCandidates(content: string): LinkPreviewCandidate[] {
   const searchable = stripHiddenLinkPreviewContent(content);
   const candidates: LinkPreviewCandidate[] = [];
   let order = 0;
 
   for (const match of searchable.matchAll(MARKDOWN_SUPPORTED_LINK_RE)) {
     if (match[0]?.startsWith("!")) continue;
+    const index = match.index ?? 0;
     candidates.push({
+      end: index + match[0].length,
       href: match[2],
-      index: match.index ?? 0,
+      index,
       label: match[1],
+      linkSource: match[2],
       order,
+      replacement: match[1],
     });
     order += 1;
   }
@@ -650,18 +660,96 @@ export function extractSupportedLinkPreviews(
     const prefix = match[1] ?? "";
     const href = match[2];
     if (!href) continue;
+    const trimmedHref = trimUrlCandidate(href);
+    let index = (match.index ?? 0) + prefix.length;
+    let end = index + trimmedHref.length;
+    if (content[index - 1] === "<" && content[end] === ">") {
+      index -= 1;
+      end += 1;
+    }
     candidates.push({
-      href,
-      index: (match.index ?? 0) + prefix.length,
+      end,
+      href: trimmedHref,
+      index,
+      linkSource: content.slice(index, end),
       order,
+      replacement: "",
     });
     order += 1;
   }
 
   candidates.sort((a, b) => a.index - b.index || a.order - b.order);
+  return candidates;
+}
+
+function collectOutgoingLinkCandidates(
+  content: string,
+): LinkPreviewCandidate[] {
+  const searchable = stripHiddenLinkPreviewContent(content);
+  const candidates = collectLinkPreviewCandidates(content);
+  let order = candidates.length;
+
+  for (const match of searchable.matchAll(MARKDOWN_OUTGOING_LINK_RE)) {
+    if (match[0]?.startsWith("!")) continue;
+    const index = match.index ?? 0;
+    candidates.push({
+      end: index + match[0].length,
+      href: match[2],
+      index,
+      label: match[1],
+      linkSource: match[2],
+      order,
+      replacement: match[1],
+    });
+    order += 1;
+  }
+
+  for (const match of searchable.matchAll(OUTGOING_URL_RE)) {
+    const prefix = match[1] ?? "";
+    const href = match[2];
+    if (!href) continue;
+    const trimmedHref = trimUrlCandidate(href);
+    let index = (match.index ?? 0) + prefix.length;
+    let end = index + trimmedHref.length;
+    if (content[index - 1] === "<" && content[end] === ">") {
+      index -= 1;
+      end += 1;
+    }
+    candidates.push({
+      end,
+      href: trimmedHref,
+      index,
+      linkSource: content.slice(index, end),
+      order,
+      replacement: "",
+    });
+    order += 1;
+  }
+
+  candidates.sort((a, b) => a.index - b.index || a.order - b.order);
+  return candidates;
+}
+
+function isOutgoingLink(href: string): boolean {
+  if (isEntityLink(href)) return true;
+  try {
+    const parsed = new URL(href);
+    return parsed.protocol === "https:" || parsed.protocol === "http:";
+  } catch {
+    return false;
+  }
+}
+
+/** Extract supported link previews from message text, preserving first-seen order. */
+export function extractSupportedLinkPreviews(
+  content: string,
+  activeRelayOrigin?: string | null,
+): SupportedLinkPreview[] {
+  const previews: SupportedLinkPreview[] = [];
+  const seen = new Set<string>();
 
   const relayOrigin = activeRelayOrigin ?? null;
-  for (const candidate of candidates) {
+  for (const candidate of collectLinkPreviewCandidates(content)) {
     const preview = parseSupportedLinkPreview(candidate.href, relayOrigin);
     if (!preview || seen.has(preview.href)) continue;
 
@@ -679,3 +767,64 @@ export function extractSupportedLinkPreviews(
 
   return previews;
 }
+
+export type OutgoingLinkContentParts = {
+  linkContent: string;
+  textContent: string;
+};
+
+/**
+ * Lift web and Buzz entity links out of authored prose without disturbing links
+ * hidden inside code, spoilers, or image markdown. Markdown link labels remain
+ * in the prose so `Review [this PR](…)` becomes `Review this PR`.
+ */
+export function splitOutgoingLinkContent(
+  content: string,
+  activeRelayOrigin?: string | null,
+): OutgoingLinkContentParts {
+  const relayOrigin = activeRelayOrigin ?? null;
+  const candidates: LinkPreviewCandidate[] = [];
+
+  for (const candidate of collectOutgoingLinkCandidates(content)) {
+    if (
+      !parseSupportedLinkPreview(candidate.href, relayOrigin) &&
+      !isOutgoingLink(candidate.href)
+    ) {
+      continue;
+    }
+    const previousCandidate = candidates[candidates.length - 1];
+    if (!previousCandidate || candidate.index >= previousCandidate.end) {
+      candidates.push(candidate);
+    }
+  }
+
+  if (candidates.length === 0) {
+    return { linkContent: "", textContent: content };
+  }
+
+  let textContent = "";
+  let cursor = 0;
+  for (const candidate of candidates) {
+    textContent += content.slice(cursor, candidate.index);
+    textContent += candidate.replacement;
+    cursor = candidate.end;
+
+    if (!candidate.replacement) {
+      if (/[ \t]$/.test(textContent) && /^[ \t]/.test(content.slice(cursor))) {
+        cursor += 1;
+      }
+      if (
+        /[ \t]$/.test(textContent) &&
+        /^(?:\n|[,.;:!?])/.test(content.slice(cursor))
+      ) {
+        textContent = textContent.replace(/[ \t]+$/, "");
+      }
+    }
+  }
+  textContent += content.slice(cursor);
+
+  return {
+    linkContent: candidates.map((candidate) => candidate.linkSource).join("\n"),
+    textContent: textContent.trim(),
+  };
+}
diff --git a/desktop/src/shared/styles/globals/markdown.css b/desktop/src/shared/styles/globals/markdown.css
index ef38b148f4..e8893751fa 100644
--- a/desktop/src/shared/styles/globals/markdown.css
+++ b/desktop/src/shared/styles/globals/markdown.css
@@ -338,11 +338,15 @@
     center / contain no-repeat;
 }
 
-.message-markdown.message-bubble-markdown .agent-mention-highlight {
-  padding-left: calc(var(--agent-icon-size) + var(--agent-icon-gap));
+.message-markdown.message-bubble-markdown .inline-chip-with-icon {
+  display: inline-block;
+  padding-left: calc(
+    var(--inline-chip-icon-size) +
+    var(--inline-chip-icon-gap)
+  );
 }
 
-.message-markdown.message-bubble-markdown .agent-mention-highlight::before {
+.message-markdown.message-bubble-markdown .inline-chip-with-icon::before {
   left: 0;
 }
 
diff --git a/desktop/tests/e2e/channels.spec.ts b/desktop/tests/e2e/channels.spec.ts
index 1b6266271e..35e5f47a52 100644
--- a/desktop/tests/e2e/channels.spec.ts
+++ b/desktop/tests/e2e/channels.spec.ts
@@ -529,10 +529,18 @@ test("channel sidebar rows use a large icon tile and description", async ({
 
   const iconContainer = page.getByTestId("channel-icon-container-general");
   await expect(iconContainer).toBeVisible();
+  await expect(page.getByTestId("channel-general")).toHaveCSS(
+    "border-radius",
+    "16px",
+  );
   await expect(iconContainer).toHaveCSS("width", "40px");
   await expect(iconContainer).toHaveCSS("height", "40px");
-  await expect(iconContainer.locator("svg")).toHaveCSS("width", "24px");
-  await expect(iconContainer.locator("svg")).toHaveCSS("height", "24px");
+  const backgroundColor = await page
+    .locator("body")
+    .evaluate((element) => getComputedStyle(element).backgroundColor);
+  await expect(iconContainer).toHaveCSS("background-color", backgroundColor);
+  await expect(iconContainer.locator("svg")).toHaveCSS("width", "16px");
+  await expect(iconContainer.locator("svg")).toHaveCSS("height", "16px");
   await expect(page.getByTestId("channel-subtitle-general")).toHaveText(
     "General discussion for everyone",
   );
diff --git a/desktop/tests/e2e/file-attachment.spec.ts b/desktop/tests/e2e/file-attachment.spec.ts
index edf07b4e60..b74e266c89 100644
--- a/desktop/tests/e2e/file-attachment.spec.ts
+++ b/desktop/tests/e2e/file-attachment.spec.ts
@@ -288,6 +288,7 @@ test("does not restore already-sent media when the text send fails", async ({
   await page.evaluate(() => {
     if (window.__BUZZ_E2E__?.mock) {
       window.__BUZZ_E2E__.mock.sendMessageErrors = [
+        "",
         "Mock accompanying text send failed.",
       ];
     }
diff --git a/desktop/tests/e2e/message-feedback-snapshots.spec.ts b/desktop/tests/e2e/message-feedback-snapshots.spec.ts
index 1ed1d486dd..f01d1cfd1b 100644
--- a/desktop/tests/e2e/message-feedback-snapshots.spec.ts
+++ b/desktop/tests/e2e/message-feedback-snapshots.spec.ts
@@ -606,6 +606,55 @@ test("direct messages use the same grouped message bubbles", async ({
   await page.screenshot({ path: `${SHOTS}/direct-message-bubbles.png` });
 });
 
+test("bubble mentions keep their prefix icon beside the name", async ({
+  page,
+}) => {
+  await seedMessageBubbles(page);
+  await installMockBridge(page);
+  await page.goto("/");
+  await page.getByTestId("channel-general").click();
+  await expect(page.getByTestId("chat-title")).toHaveText("general");
+  await waitForMockLiveSubscription(page, "general");
+
+  const content = `Bubble mention @bob ${Date.now()}`;
+  const visibleContent = content.replace("@", "");
+  await page.evaluate(
+    ({ bobPubkey, message }) => {
+      window.__BUZZ_E2E_EMIT_MOCK_MESSAGE__?.({
+        channelName: "general",
+        content: message,
+        mentionPubkeys: [bobPubkey],
+      });
+    },
+    { bobPubkey: TEST_IDENTITIES.bob.pubkey, message: content },
+  );
+
+  const mention = page
+    .getByTestId("message-row")
+    .filter({ hasText: visibleContent })
+    .locator("[data-mention]");
+  await expect(mention).toHaveText("bob");
+  const geometry = await mention.evaluate((element) => {
+    const style = getComputedStyle(element);
+    const iconStyle = getComputedStyle(element, "::before");
+    const textNode = element.firstChild;
+    if (!textNode) throw new Error("Expected mention label text.");
+    const range = document.createRange();
+    range.selectNodeContents(textNode);
+    const elementBox = element.getBoundingClientRect();
+    return {
+      iconRight:
+        elementBox.left +
+        Number.parseFloat(iconStyle.left) +
+        Number.parseFloat(iconStyle.width),
+      paddingLeft: Number.parseFloat(style.paddingLeft),
+      textLeft: range.getBoundingClientRect().left,
+    };
+  });
+  expect(geometry.paddingLeft).toBeGreaterThan(0);
+  expect(geometry.iconRight).toBeLessThanOrEqual(geometry.textLeft + 0.5);
+});
+
 test("own-message bubbles align right and use the primary token", async ({
   page,
 }) => {
diff --git a/desktop/tests/e2e/messaging.spec.ts b/desktop/tests/e2e/messaging.spec.ts
index 0e619e5a9c..028415ca1e 100644
--- a/desktop/tests/e2e/messaging.spec.ts
+++ b/desktop/tests/e2e/messaging.spec.ts
@@ -1285,6 +1285,91 @@ test("rapid Enter presses on a ready link preview send exactly once", async ({
     .toBe(1);
 });
 
+test("mixed link preview and prose send as separate link-first messages", async ({
+  page,
+}) => {
+  const previewUrl = "https://github.com/block/buzz/pull/3246?split=1";
+  const prose = `Context for the shared link ${Date.now()}`;
+  await page.goto("/");
+  await page.getByTestId("channel-general").click();
+  const input = page.getByTestId("message-input");
+  await input.fill(`${prose} ${previewUrl}`);
+  await waitForReadyComposerSnapshots(page);
+  await page.getByTestId("send-message").click();
+
+  const rows = page.getByTestId("message-row");
+  const linkRow = rows
+    .filter({ has: page.locator("[data-link-preview]") })
+    .last();
+  const proseRow = rows.filter({ hasText: prose });
+  await expect(linkRow).toContainText(previewUrl);
+  await expect(linkRow).not.toContainText(prose);
+  await expect(proseRow).toBeVisible();
+  await expect(proseRow.locator("[data-link-preview]")).toHaveCount(0);
+
+  const [linkBox, proseBox] = await Promise.all([
+    linkRow.boundingBox(),
+    proseRow.boundingBox(),
+  ]);
+  if (!linkBox || !proseBox) {
+    throw new Error("Expected separate link and prose message geometry.");
+  }
+  expect(linkBox.y).toBeLessThan(proseBox.y);
+
+  const calls = await page.evaluate(() =>
+    (window.__BUZZ_E2E_COMMAND_PAYLOADS__ ?? []).filter(
+      (entry) => entry.command === "send_channel_message",
+    ),
+  );
+  expect(calls).toHaveLength(2);
+  expect(calls[0]?.payload).toMatchObject({
+    content: previewUrl,
+    mentionPubkeys: [],
+  });
+  expect(
+    (calls[0]?.payload as { linkPreviewTags?: string[][] }).linkPreviewTags,
+  ).toHaveLength(1);
+  expect(calls[1]?.payload).toMatchObject({ content: prose });
+  expect(
+    (calls[1]?.payload as { linkPreviewTags?: string[][] }).linkPreviewTags ??
+      [],
+  ).toEqual([]);
+});
+
+test("a failed prose send restores text without duplicating its sent link preview", async ({
+  page,
+}) => {
+  const previewUrl = "https://github.com/block/buzz/pull/3246?retry=1";
+  const prose = `Retry only this link context ${Date.now()}`;
+  await page.goto("/");
+  await page.evaluate(() => {
+    if (window.__BUZZ_E2E__?.mock) {
+      window.__BUZZ_E2E__.mock.sendMessageErrors = [
+        "",
+        "Mock accompanying prose send failed.",
+      ];
+    }
+  });
+  await page.getByTestId("channel-general").click();
+  const input = page.getByTestId("message-input");
+  await input.fill(`${prose} ${previewUrl}`);
+  await waitForReadyComposerSnapshots(page);
+  await page.getByTestId("send-message").click();
+
+  await expect(page.locator("[data-link-preview]")).toHaveCount(1);
+  await expect(input).toContainText(prose);
+  await expect(input).not.toContainText(previewUrl);
+  await expect(
+    page.getByTestId("message-row").filter({ hasText: prose }),
+  ).toHaveCount(0);
+
+  await input.press("Enter");
+  await expect(
+    page.getByTestId("message-row").filter({ hasText: prose }),
+  ).toBeVisible();
+  await expect(page.locator("[data-link-preview]")).toHaveCount(1);
+});
+
 test("pasting a link and immediately pressing Enter prepares it after submit", async ({
   page,
 }) => {