diff --git a/src/tools/skill/session-skill-cache.ts b/src/tools/skill/session-skill-cache.ts
new file mode 100644
index 000000000..040979ddb
--- /dev/null
+++ b/src/tools/skill/session-skill-cache.ts
@@ -0,0 +1,10 @@
+const seenSessionIDs = new Set<string>()
+
+export function shouldInvalidateSkillCacheForSession(sessionID?: string): boolean {
+  if (!sessionID || seenSessionIDs.has(sessionID)) {
+    return false
+  }
+
+  seenSessionIDs.add(sessionID)
+  return true
+}
diff --git a/src/tools/skill/tools.factory.test.ts b/src/tools/skill/tools.factory.test.ts
index e52f0abb5..5b9a5ba30 100644
--- a/src/tools/skill/tools.factory.test.ts
+++ b/src/tools/skill/tools.factory.test.ts
@@ -4,7 +4,6 @@ import { afterEach, beforeEach, describe, expect, it, mock, spyOn } from "bun:te
 import type { ToolContext } from "@opencode-ai/plugin/tool"
 import type { LoadedSkill } from "../../features/opencode-skill-loader/types"
 import * as skillContent from "../../features/opencode-skill-loader/skill-content"
-import * as commandDiscovery from "../slashcommand/command-discovery"
 
 const discoverCommandsSync = mock(() => [])
 
@@ -94,19 +93,21 @@ describe("createSkillTool", () => {
     expect(getAllSkills.mock.calls.length).toBe(baselineGetAllSkillsCalls + 1)
   })
 
-  it("does not clear the shared skill cache during description or execute refresh", async () => {
+  it("clears the shared skill cache once on first execute in a session", async () => {
     // given
     const baselineClearSkillCacheCalls = clearSkillCache.mock.calls.length
+    const sessionContext = createMockContext("session-clear-once")
 
     // when
     const { createSkillTool } = await import("./tools")
     const skillTool = createSkillTool({})
     void skillTool.description
     await flushMicrotasks()
-		await skillTool.execute({ name: "lazy-skill" }, mockContext)
+    await skillTool.execute({ name: "lazy-skill" }, sessionContext)
+    await skillTool.execute({ name: "lazy-skill" }, sessionContext)
 
     // then
-    expect(clearSkillCache.mock.calls.length).toBe(baselineClearSkillCacheCalls)
+    expect(clearSkillCache.mock.calls.length).toBe(baselineClearSkillCacheCalls + 1)
   })
 
   it("clears the skill discovery cache once per session", async () => {
diff --git a/src/tools/skill/tools.ts b/src/tools/skill/tools.ts
index f60d06492..d49936f95 100644
--- a/src/tools/skill/tools.ts
+++ b/src/tools/skill/tools.ts
@@ -2,9 +2,10 @@ import { dirname } from "node:path"
 import { tool, type ToolDefinition } from "@opencode-ai/plugin"
 import type { ToolContext } from "@opencode-ai/plugin/tool"
 import { TOOL_DESCRIPTION_PREFIX } from "./constants"
+import { shouldInvalidateSkillCacheForSession } from "./session-skill-cache"
 import type { SkillArgs, SkillLoadOptions } from "./types"
 import type { LoadedSkill } from "../../features/opencode-skill-loader"
-import { getAllSkills } from "../../features/opencode-skill-loader/skill-content"
+import { clearSkillCache, getAllSkills } from "../../features/opencode-skill-loader/skill-content"
 import { injectGitMasterConfig } from "../../features/opencode-skill-loader/skill-content"
 import { discoverCommandsSync } from "../slashcommand/command-discovery"
 import type { CommandInfo } from "../slashcommand/types"
@@ -27,7 +28,11 @@ import {
 export function createSkillTool(options: SkillLoadOptions = {}): ToolDefinition {
   let cachedDescription: string | null = null
 
-  const getSkills = async (): Promise<LoadedSkill[]> => {
+  const getSkills = async (context?: ToolContext): Promise<LoadedSkill[]> => {
+    if (shouldInvalidateSkillCacheForSession(context?.sessionID)) {
+      clearSkillCache()
+    }
+
     const discovered = (await getAllSkills({
       disabledSkills: options?.disabledSkills,
       browserProvider: options?.browserProvider,
@@ -108,7 +113,7 @@ export function createSkillTool(options: SkillLoadOptions = {}): ToolDefinition
         .describe("Optional arguments or context for command invocation. Example: name='publish', user_message='patch'"),
     },
     async execute(args: SkillArgs, ctx?: ToolContext) {
-      const skills = await getSkills()
+      const skills = await getSkills(ctx)
       const commands = getCommands()
       cachedDescription = formatCombinedDescription(skills.map(loadedSkillToInfo), commands)