diff --git a/.changeset/fix-skill-read-duplicates.md b/.changeset/fix-skill-read-duplicates.md
new file mode 100644
index 0000000..d12accd
--- /dev/null
+++ b/.changeset/fix-skill-read-duplicates.md
@@ -0,0 +1,5 @@
+---
+"@jmfederico/pi-web": patch
+---
+
+Prevent live skill-loading cards from duplicating when the finalized transcript groups multiple skill reads.
diff --git a/src/client/src/chatMessages.ts b/src/client/src/chatMessages.ts
index ceec115..5294b14 100644
--- a/src/client/src/chatMessages.ts
+++ b/src/client/src/chatMessages.ts
@@ -162,9 +162,9 @@ function normalizeContent(content: unknown, message: unknown): ChatPart[] {
     if (type === "toolCall") {
       const toolName = getString(part, "name") ?? "tool";
       const args = getProperty(part, "arguments");
-      const skillRead = toolName === "read" ? parseSkillReadPath(getString(args, "path")) : undefined;
-      if (skillRead !== undefined) return [{ type: "skillRead", ...skillRead }];
       const toolCallId = getString(part, "id");
+      const skillRead = toolName === "read" ? parseSkillReadPath(getString(args, "path")) : undefined;
+      if (skillRead !== undefined) return [{ type: "skillRead", ...skillRead, ...(toolCallId === undefined ? {} : { toolCallId }) }];
       return [{ type: "toolCall", ...(toolCallId === undefined ? {} : { toolCallId }), toolName, summary: summarizeArgs(args), ...(args === undefined ? {} : { args }) }];
     }
     if (type === "image") {
diff --git a/src/client/src/chatTranscript.test.ts b/src/client/src/chatTranscript.test.ts
index a4454eb..09c349b 100644
--- a/src/client/src/chatTranscript.test.ts
+++ b/src/client/src/chatTranscript.test.ts
@@ -101,8 +101,9 @@ describe("applyTranscriptEvent", () => {
     ]);
   });
 
-  it("replaces streamed skill reads when the finalized assistant message includes thinking", () => {
+  it("replaces streamed thinking and skill reads when the finalized assistant message includes thinking", () => {
     const streamed: ChatLine[] = [
+      { role: "assistant", parts: [{ type: "thinking", text: "load skill" }] },
       { role: "skill", parts: [{ type: "skillRead", name: "playwright", path: "/skills/playwright/SKILL.md" }] },
       { role: "tool", parts: [{ type: "toolResult", toolName: "read", text: "skill content", isError: false }] },
     ];
@@ -174,8 +175,8 @@ describe("applyTranscriptEvent", () => {
     messages = applyTranscriptEvent(messages, { type: "tool.start", toolName: "read", toolCallId: "2", summary: "", args: { path: "/skills/sentry-cli/SKILL.md" } }) ?? messages;
 
     expect(messages).toEqual([
-      { role: "skill", parts: [{ type: "skillRead", name: "playwright", path: "/skills/playwright/SKILL.md" }] },
-      { role: "skill", parts: [{ type: "skillRead", name: "sentry-cli", path: "/skills/sentry-cli/SKILL.md" }] },
+      { role: "skill", parts: [{ type: "skillRead", name: "playwright", path: "/skills/playwright/SKILL.md", toolCallId: "1" }] },
+      { role: "skill", parts: [{ type: "skillRead", name: "sentry-cli", path: "/skills/sentry-cli/SKILL.md", toolCallId: "2" }] },
     ]);
   });
 
@@ -185,6 +186,74 @@ describe("applyTranscriptEvent", () => {
     messages = applyTranscriptEvent(messages, { type: "tool.start", toolName: "read", toolCallId: "1", summary: "", args: { path: "/skills/playwright/SKILL.md" } }) ?? messages;
 
     expect(messages).toEqual([
+      { role: "skill", parts: [{ type: "skillRead", name: "playwright", path: "/skills/playwright/SKILL.md", toolCallId: "1" }] },
+    ]);
+  });
+
+  it("replaces multiple streamed skill reads with the finalized grouped skill message", () => {
+    const firstTool: ChatLine = { role: "tool", parts: [{ type: "toolExecution", toolCallId: "read-1", toolName: "read", summary: "/skills/code-quality-architecture/SKILL.md", status: "success", resultText: "content" }] };
+    const secondTool: ChatLine = { role: "tool", parts: [{ type: "toolExecution", toolCallId: "read-2", toolName: "read", summary: "/skills/relay/SKILL.md", status: "success", resultText: "content" }] };
+    const thirdTool: ChatLine = { role: "tool", parts: [{ type: "toolExecution", toolCallId: "read-3", toolName: "read", summary: "/skills/skill-creator/SKILL.md", status: "success", resultText: "content" }] };
+    const streamed: ChatLine[] = [
+      { role: "skill", parts: [{ type: "skillRead", name: "code-quality-architecture", path: "/skills/code-quality-architecture/SKILL.md", toolCallId: "read-1" }] },
+      firstTool,
+      { role: "skill", parts: [{ type: "skillRead", name: "relay", path: "/skills/relay/SKILL.md", toolCallId: "read-2" }] },
+      secondTool,
+      { role: "skill", parts: [{ type: "skillRead", name: "skill-creator", path: "/skills/skill-creator/SKILL.md", toolCallId: "read-3" }] },
+      thirdTool,
+    ];
+
+    expect(applyTranscriptEvent(streamed, {
+      type: "message.end",
+      message: {
+        role: "assistant",
+        content: [
+          { type: "toolCall", id: "read-1", name: "read", arguments: { path: "/skills/code-quality-architecture/SKILL.md" } },
+          { type: "toolCall", id: "read-2", name: "read", arguments: { path: "/skills/relay/SKILL.md" } },
+          { type: "toolCall", id: "read-3", name: "read", arguments: { path: "/skills/skill-creator/SKILL.md" } },
+        ],
+        timestamp: "2026-05-09T12:00:00.000Z",
+      },
+    })).toEqual([
+      {
+        role: "skill",
+        parts: [
+          { type: "skillRead", name: "code-quality-architecture", path: "/skills/code-quality-architecture/SKILL.md", toolCallId: "read-1" },
+          { type: "skillRead", name: "relay", path: "/skills/relay/SKILL.md", toolCallId: "read-2" },
+          { type: "skillRead", name: "skill-creator", path: "/skills/skill-creator/SKILL.md", toolCallId: "read-3" },
+        ],
+        meta: { timestamp: "2026-05-09T12:00:00.000Z" },
+      },
+      firstTool,
+      secondTool,
+      thirdTool,
+    ]);
+  });
+
+  it("ignores streamed skill read starts that are already in a finalized grouped skill message", () => {
+    const messages: ChatLine[] = [
+      {
+        role: "skill",
+        parts: [
+          { type: "skillRead", name: "code-quality-architecture", path: "/skills/code-quality-architecture/SKILL.md", toolCallId: "read-1" },
+          { type: "skillRead", name: "relay", path: "/skills/relay/SKILL.md", toolCallId: "read-2" },
+        ],
+        meta: { timestamp: "2026-05-09T12:00:00.000Z" },
+      },
+      { role: "tool", parts: [{ type: "toolExecution", toolCallId: "read-1", toolName: "read", summary: "/skills/code-quality-architecture/SKILL.md", status: "success", resultText: "content" }] },
+    ];
+
+    expect(applyTranscriptEvent(messages, { type: "tool.start", toolName: "read", toolCallId: "read-2", summary: "", args: { path: "/skills/relay/SKILL.md" } })).toEqual(messages);
+  });
+
+  it("allows the same skill read after a user boundary", () => {
+    const messages: ChatLine[] = [
+      { role: "skill", parts: [{ type: "skillRead", name: "playwright", path: "/skills/playwright/SKILL.md" }] },
+      textMessage("user", "load it again"),
+    ];
+
+    expect(applyTranscriptEvent(messages, { type: "tool.start", toolName: "read", toolCallId: "", summary: "", args: { path: "/skills/playwright/SKILL.md" } })).toEqual([
+      ...messages,
       { role: "skill", parts: [{ type: "skillRead", name: "playwright", path: "/skills/playwright/SKILL.md" }] },
     ]);
   });
diff --git a/src/client/src/chatTranscript.ts b/src/client/src/chatTranscript.ts
index 84e976d..bad38d5 100644
--- a/src/client/src/chatTranscript.ts
+++ b/src/client/src/chatTranscript.ts
@@ -35,8 +35,8 @@ function applyFinalMessage(messages: ChatLine[], rawMessage: unknown): ChatLine[
 }
 
 function applyFinalLine(messages: ChatLine[], displayEnded: ChatLine): ChatLine[] {
-  const skillReadIndex = findMatchingSkillRead(messages, displayEnded);
-  if (skillReadIndex >= 0) return [...messages.slice(0, skillReadIndex), displayEnded, ...messages.slice(skillReadIndex + 1)];
+  const skillReadIndexes = findMatchingSkillReadIndexes(messages, displayEnded);
+  if (skillReadIndexes.length > 0) return replaceSkillReadLines(messages, skillReadIndexes, displayEnded);
   const last = messages.at(-1);
   if (last?.role !== displayEnded.role) return [...messages, displayEnded];
   if (displayEnded.role === "assistant" || sameMessageText(last, displayEnded)) return [...messages.slice(0, -1), displayEnded];
@@ -58,7 +58,9 @@ function parseSkillReadPath(path: string | undefined): { name: string; path: str
 
 function appendToolExecutionStart(messages: ChatLine[], event: Extract<SessionUiEvent, { type: "tool.start" }>): ChatLine[] {
   const skillRead = event.toolName === "read" ? parseSkillReadPath(getString(event.args, "path")) : undefined;
-  if (skillRead !== undefined) return appendLine(messages, { role: "skill", parts: [{ type: "skillRead", ...skillRead }] });
+  if (skillRead !== undefined) {
+    return appendLine(messages, { role: "skill", parts: [{ type: "skillRead", ...skillRead, ...(event.toolCallId === "" ? {} : { toolCallId: event.toolCallId }) }] });
+  }
 
   const part: ToolExecutionPart = {
     type: "toolExecution",
@@ -151,16 +153,51 @@ function stringifyToolContent(content: unknown): string {
   return "";
 }
 
-function findMatchingSkillRead(messages: ChatLine[], ended: ChatLine): number {
+function findMatchingSkillReadIndexes(messages: ChatLine[], ended: ChatLine): number[] {
   const endedReads = skillReads(ended);
-  if (endedReads.length === 0) return -1;
-  for (let index = messages.length - 1; index >= 0; index--) {
-    const message = messages[index];
-    if (message?.role !== "skill") continue;
-    const reads = skillReads(message);
-    if (sameSkillReads(reads, endedReads)) return index;
+  if (endedReads.length === 0) return [];
+
+  const matchedIndexes: number[] = [];
+  let readEnd = endedReads.length;
+  const lowerBound = lastUserBoundaryIndex(messages) + 1;
+
+  for (let index = messages.length - 1; index >= lowerBound; index--) {
+    const reads = skillReads(messages[index]);
+    if (reads.length === 0) continue;
+    const readStart = readEnd - reads.length;
+    if (readStart < 0) continue;
+    if (!sameSkillReads(reads, endedReads.slice(readStart, readEnd))) continue;
+    matchedIndexes.unshift(index);
+    readEnd = readStart;
+    if (readEnd === 0) return matchedIndexes;
   }
-  return -1;
+
+  return [];
+}
+
+function replaceSkillReadLines(messages: ChatLine[], indexes: number[], replacement: ChatLine): ChatLine[] {
+  const replacementIndexes = indexesWithAdjacentAssistantFragment(messages, indexes, replacement);
+  const insertIndex = replacementIndexes[0];
+  if (insertIndex === undefined) return messages;
+  const replaced = new Set(replacementIndexes);
+  const next: ChatLine[] = [];
+  for (let index = 0; index < messages.length; index++) {
+    if (index === insertIndex) next.push(replacement);
+    const message = messages[index];
+    if (message !== undefined && !replaced.has(index)) next.push(message);
+  }
+  return next;
+}
+
+function indexesWithAdjacentAssistantFragment(messages: ChatLine[], indexes: number[], replacement: ChatLine): number[] {
+  const firstIndex = indexes[0];
+  if (replacement.role !== "assistant" || firstIndex === undefined) return indexes;
+  const previousIndex = firstIndex - 1;
+  return isStreamedAssistantFragment(messages[previousIndex]) ? [previousIndex, ...indexes] : indexes;
+}
+
+function isStreamedAssistantFragment(message: ChatLine | undefined): boolean {
+  return message?.role === "assistant" && message.parts.length > 0 && message.parts.every((part) => part.type === "text" || part.type === "thinking");
 }
 
 function skillReads(message: ChatLine | undefined): SkillRead[] {
@@ -176,6 +213,7 @@ function sameSkillReads(left: SkillRead[], right: SkillRead[]): boolean {
 
 function sameSkillRead(left: SkillRead, right: SkillRead | undefined): boolean {
   if (right === undefined) return false;
+  if (left.toolCallId !== undefined && right.toolCallId !== undefined) return left.toolCallId === right.toolCallId;
   return normalizeSkillPath(left.path) === normalizeSkillPath(right.path) || left.name === right.name;
 }
 
@@ -201,11 +239,32 @@ function appendNewMessage(messages: ChatLine[], rawMessage: unknown): ChatLine[]
 
 function appendLine(messages: ChatLine[], line: ChatLine): ChatLine[] {
   const last = messages.at(-1);
-  if (line.role === "skill" && sameSkillReads(skillReads(last), skillReads(line))) return messages;
+  if (isDuplicateSkillLine(messages, line)) return messages;
   if (last?.role === line.role && line.role !== "skill") return [...messages.slice(0, -1), { ...last, parts: [...last.parts, ...line.parts] }];
   return [...messages, line];
 }
 
+function isDuplicateSkillLine(messages: ChatLine[], line: ChatLine): boolean {
+  const reads = skillReads(line);
+  if (line.role !== "skill" || reads.length === 0) return false;
+  const lowerBound = lastUserBoundaryIndex(messages) + 1;
+  return reads.every((read) => hasMatchingSkillRead(messages, read, lowerBound));
+}
+
+function hasMatchingSkillRead(messages: ChatLine[], read: SkillRead, lowerBound: number): boolean {
+  for (let index = messages.length - 1; index >= lowerBound; index--) {
+    if (skillReads(messages[index]).some((candidate) => sameSkillRead(candidate, read))) return true;
+  }
+  return false;
+}
+
+function lastUserBoundaryIndex(messages: ChatLine[]): number {
+  for (let index = messages.length - 1; index >= 0; index--) {
+    if (messages[index]?.role === "user") return index;
+  }
+  return -1;
+}
+
 function isRecord(value: unknown): value is Record<string, unknown> {
   return typeof value === "object" && value !== null;
 }
diff --git a/src/client/src/components/shared.ts b/src/client/src/components/shared.ts
index a179efc..91165e5 100644
--- a/src/client/src/components/shared.ts
+++ b/src/client/src/components/shared.ts
@@ -24,7 +24,7 @@ export type ChatPart =
   | { type: "image"; mimeType: string; data: string }
   | { type: "thinking"; text: string }
   | { type: "skillInvocation"; name: string; location: string; content: string }
-  | { type: "skillRead"; name: string; path: string }
+  | { type: "skillRead"; name: string; path: string; toolCallId?: string }
   | { type: "toolCall"; toolCallId?: string; toolName: string; summary: string; args?: unknown }
   | ToolExecutionPart
   | { type: "toolResult"; toolCallId?: string; toolName: string; text: string; isError: boolean; content?: unknown; details?: unknown }