diff --git a/packages/support/acp-snapshot/src/normalize.ts b/packages/support/acp-snapshot/src/normalize.ts
index f984c231ea..e010afebcb 100644
--- a/packages/support/acp-snapshot/src/normalize.ts
+++ b/packages/support/acp-snapshot/src/normalize.ts
@@ -22,6 +22,7 @@ const EVENT_READ_OMITTED_BYTES_RE = /(\r?\n\r?\n\(Omitted )\d+( bytes\.)/g
 const EVENT_READ_TARGET_REGION_RE
   = /^Session [^\r\n]+ — [^\r\n]+\r?\nTarget event seq \d+:\r?\n```json\r?\n\{\r?\n[\s\S]*?(?=\r?\n```(?:\r?\n|$)|\r?\n\r?\n\(Omitted )/
 const PATH_TEXT_BOUNDARY_RE = /[\s<>'"`()\[\]{},;:!?=]/
+const FILE_URI_PATH_PREFIX_RE = /(?:^|[^a-z0-9+.-])file:\/\/\/?$/i
 
 /** A UUID v4 string, the shape `randomUUID()` produces for session ids. */
 const UUID_RE = /[0-9a-f]{8}-[0-9a-f]{4}-[0-9a-f]{4}-[0-9a-f]{4}-[0-9a-f]{12}/gi
@@ -97,12 +98,14 @@ function isCwdMatch(value: string, start: number, length: number): boolean {
   const before = value[start - 1]
   const after = value[start + length]
   const afterPunctuation = value[start + length + 1]
-  const startsAtBoundary = before === undefined || PATH_TEXT_BOUNDARY_RE.test(before)
+  const startsAtBoundary = before === undefined
+    || PATH_TEXT_BOUNDARY_RE.test(before)
+    || FILE_URI_PATH_PREFIX_RE.test(value.slice(0, start))
   const endsAtBoundary = after === undefined
     || after === '/'
     || after === '\\'
     || PATH_TEXT_BOUNDARY_RE.test(after)
-    || after === '.' && (afterPunctuation === undefined || /\s/.test(afterPunctuation))
+    || after === '.' && (afterPunctuation === undefined || PATH_TEXT_BOUNDARY_RE.test(afterPunctuation))
   return startsAtBoundary && endsAtBoundary
 }
 
diff --git a/packages/support/acp-snapshot/tests/normalize.spec.ts b/packages/support/acp-snapshot/tests/normalize.spec.ts
index a2c824519e..8bc6a66d14 100644
--- a/packages/support/acp-snapshot/tests/normalize.spec.ts
+++ b/packages/support/acp-snapshot/tests/normalize.spec.ts
@@ -46,6 +46,28 @@ describe('normalizeStdout', () => {
     expect(out).not.toContain(ctx.sessionIds[0] as string)
   })
 
+  it('scrubs cwd at file URI and chained-punctuation boundaries', () => {
+    const raw = JSON.stringify({
+      jsonrpc: '2.0',
+      method: 'session/update',
+      params: {
+        uri: `file://${ctx.cwd}/proof.txt`,
+        punctuated: `${ctx.cwd}.,`,
+        dottedSegment: `${ctx.cwd}.backup`,
+        dashedSegment: `${ctx.cwd}-backup`,
+      },
+    })
+    const frame = JSON.parse(normalizeStdout(raw, ctx)) as {
+      params: Record<string, string>
+    }
+    expect(frame.params).toEqual({
+      uri: 'file://{{cwd}}/proof.txt',
+      punctuated: '{{cwd}}.,',
+      dottedSegment: `${ctx.cwd}.backup`,
+      dashedSegment: `${ctx.cwd}-backup`,
+    })
+  })
+
   it('scrubs every filesystem spelling of the cwd longest-first', () => {
     const longCwd = String.raw`C:\Users\runneradmin\AppData\Local\Temp\acp-snapshot`
     const aliasedCtx: NormalizeContext = {
@@ -213,6 +235,22 @@ describe('normalizeSessionLog', () => {
     expect(out).not.toContain(ctx.cwd)
   })
 
+  it('scrubs cwd at file URI and chained-punctuation boundaries in event data', () => {
+    const ev = JSON.stringify({
+      type: 'tool/result',
+      seq: 2,
+      time: 5,
+      data: {
+        uri: `file://${ctx.cwd}/proof.txt`,
+        punctuated: `${ctx.cwd}.,`,
+      },
+    })
+    const out = normalizeSessionLog(`${header({ cwd: ctx.cwd })}\n${ev}\n`, ctx)
+    expect(out).toContain('file://{{cwd}}/proof.txt')
+    expect(out).toContain('{{cwd}}.,')
+    expect(out).not.toContain(`file://${ctx.cwd}`)
+  })
+
   it('scrubs random local spill paths under the snapshot cwd', () => {
     const ev = JSON.stringify({
       type: 'tool/result', seq: 2, time: 5,