diff --git a/packages/opencode/src/server/routes/instance/httpapi/handlers/v2/session.ts b/packages/opencode/src/server/routes/instance/httpapi/handlers/v2/session.ts
index 275fa2956c44..6c62f0921bc4 100644
--- a/packages/opencode/src/server/routes/instance/httpapi/handlers/v2/session.ts
+++ b/packages/opencode/src/server/routes/instance/httpapi/handlers/v2/session.ts
@@ -1,4 +1,5 @@
 import { WorkspaceID } from "@/control-plane/schema"
+import { sameDirectory } from "@/session/directory"
 import { SessionV2 } from "@/v2/session"
 import { Effect, Schema } from "effect"
 import { HttpApiBuilder, HttpApiError, HttpApiSchema } from "effect/unstable/httpapi"
@@ -43,7 +44,7 @@ function hasCursorRoutingMismatch(
   decoded: SessionCursor | undefined,
 ) {
   if (!decoded) return false
-  if (query.directory !== undefined && query.directory !== decoded.directory) return true
+  if (query.directory !== undefined && !sameDirectory(query.directory, decoded.directory)) return true
   return query.workspace !== undefined && query.workspace !== decoded.workspaceID
 }
 
diff --git a/packages/opencode/src/session/directory.ts b/packages/opencode/src/session/directory.ts
new file mode 100644
index 000000000000..8cffe6e1c954
--- /dev/null
+++ b/packages/opencode/src/session/directory.ts
@@ -0,0 +1,31 @@
+import { AppFileSystem } from "@opencode-ai/core/filesystem"
+
+export function directoryVariants(input: string | undefined) {
+  if (!input) return []
+  const values = new Set<string>()
+  values.add(input)
+
+  const resolved = resolveDirectory(input)
+  values.add(resolved)
+
+  if (process.platform !== "win32") return [...values]
+
+  values.add(input.replaceAll("\\", "/"))
+  values.add(resolved.replaceAll("\\", "/"))
+  return [...values]
+}
+
+export function sameDirectory(a: string | undefined, b: string | undefined) {
+  if (a === b) return true
+  if (!a || !b) return false
+  const values = new Set(directoryVariants(a))
+  return directoryVariants(b).some((value) => values.has(value))
+}
+
+function resolveDirectory(input: string) {
+  try {
+    return AppFileSystem.resolve(input)
+  } catch {
+    return input
+  }
+}
diff --git a/packages/opencode/src/session/session.ts b/packages/opencode/src/session/session.ts
index 797a635eeef8..520e761743cd 100644
--- a/packages/opencode/src/session/session.ts
+++ b/packages/opencode/src/session/session.ts
@@ -28,6 +28,7 @@ import { MessageV2 } from "./message-v2"
 import type { InstanceContext } from "../project/instance-context"
 import { InstanceState } from "@/effect/instance-state"
 import { Snapshot } from "@/snapshot"
+import { directoryVariants } from "./directory"
 import { ProjectID } from "../project/schema"
 import { WorkspaceID } from "../control-plane/schema"
 import { SessionID, MessageID, PartID } from "./schema"
@@ -894,6 +895,7 @@ function* listByProject(
   },
 ) {
   const conditions = [eq(SessionTable.project_id, input.projectID)]
+  const directories = directoryVariants(input.directory)
 
   if (input.workspaceID) {
     conditions.push(eq(SessionTable.workspace_id, input.workspaceID))
@@ -903,14 +905,14 @@ function* listByProject(
       const conds = [eq(SessionTable.path, input.path), like(SessionTable.path, `${input.path}/%`)]
 
       conditions.push(
-        input.directory
-          ? or(...conds, and(isNull(SessionTable.path), eq(SessionTable.directory, input.directory))!)!
+        directories.length > 0
+          ? or(...conds, and(isNull(SessionTable.path), matchDirectory(SessionTable.directory, directories))!)!
           : or(...conds)!,
       )
     }
   } else if (input.scope !== "project" && !input.experimentalWorkspaces) {
-    if (input.directory) {
-      conditions.push(eq(SessionTable.directory, input.directory))
+    if (directories.length > 0) {
+      conditions.push(matchDirectory(SessionTable.directory, directories))
     }
   }
   if (input.roots) {
@@ -949,9 +951,10 @@ export function* listGlobal(input?: {
   archived?: boolean
 }) {
   const conditions: SQL[] = []
+  const directories = directoryVariants(input?.directory)
 
-  if (input?.directory) {
-    conditions.push(eq(SessionTable.directory, input.directory))
+  if (directories.length > 0) {
+    conditions.push(matchDirectory(SessionTable.directory, directories))
   }
   if (input?.roots) {
     conditions.push(isNull(SessionTable.parent_id))
@@ -1008,4 +1011,9 @@ export function* listGlobal(input?: {
   }
 }
 
+function matchDirectory(column: typeof SessionTable.directory, directories: string[]) {
+  if (directories.length === 1) return eq(column, directories[0]!)
+  return or(...directories.map((directory) => eq(column, directory)))!
+}
+
 export * as Session from "./session"
diff --git a/packages/opencode/src/v2/session.ts b/packages/opencode/src/v2/session.ts
index a3c386f66d4f..eab3fae3e640 100644
--- a/packages/opencode/src/v2/session.ts
+++ b/packages/opencode/src/v2/session.ts
@@ -14,6 +14,7 @@ import { EventV2 } from "@opencode-ai/core/event"
 import { EventV2Bridge } from "@/event-v2-bridge"
 import { ModelV2 } from "@opencode-ai/core/model"
 import { ProviderV2 } from "@opencode-ai/core/provider"
+import { directoryVariants } from "@/session/directory"
 
 export const Delivery = Schema.Literals(["immediate", "deferred"]).annotate({
   identifier: "Session.Delivery",
@@ -181,7 +182,8 @@ export const layer = Layer.effect(
         if (direction === "previous" && order === "asc") order = "desc"
         if (direction === "previous" && order === "desc") order = "asc"
         const conditions: SQL[] = []
-        if (input.directory) conditions.push(eq(SessionTable.directory, input.directory))
+        const directories = directoryVariants(input.directory)
+        if (directories.length > 0) conditions.push(matchDirectory(directories))
         if (input.path)
           conditions.push(or(eq(SessionTable.path, input.path), like(SessionTable.path, `${input.path}/%`))!)
         if (input.workspaceID) conditions.push(eq(SessionTable.workspace_id, input.workspaceID))
@@ -334,6 +336,11 @@ export const layer = Layer.effect(
   }),
 )
 
+function matchDirectory(directories: string[]) {
+  if (directories.length === 1) return eq(SessionTable.directory, directories[0]!)
+  return or(...directories.map((directory) => eq(SessionTable.directory, directory)))!
+}
+
 export const defaultLayer = layer.pipe(Layer.provide(EventV2Bridge.defaultLayer))
 
 export * as SessionV2 from "./session"
diff --git a/packages/opencode/test/server/session-list.test.ts b/packages/opencode/test/server/session-list.test.ts
index 4aab0c4b1f37..bd676c1db44d 100644
--- a/packages/opencode/test/server/session-list.test.ts
+++ b/packages/opencode/test/server/session-list.test.ts
@@ -14,6 +14,7 @@ import { Storage } from "@/storage/storage"
 import { SyncEvent } from "@/sync"
 import { RuntimeFlags } from "@/effect/runtime-flags"
 import { BackgroundJob } from "@/background/job"
+import { sameDirectory } from "@/session/directory"
 
 void Log.init({ print: false })
 const it = testEffect(
@@ -37,6 +38,13 @@ afterEach(async () => {
 })
 
 describe("session.list", () => {
+  it.effect("treats slash-equivalent Windows directories as equal", () => {
+    if (process.platform !== "win32") return Effect.void
+    expect(sameDirectory("C:/repo/demo", "C:\\repo\\demo")).toBe(true)
+    expect(sameDirectory("C:/repo/demo", "C:/repo/other")).toBe(false)
+    return Effect.void
+  })
+
   it.instance(
     "does not filter by directory when directory is omitted",
     () =>
@@ -65,6 +73,26 @@ describe("session.list", () => {
     { git: true },
   )
 
+  it.instance(
+    "matches slash-equivalent directory filters on Windows",
+    () =>
+      Effect.gen(function* () {
+        if (process.platform !== "win32") return
+        const test = yield* TestInstance
+        yield* Effect.promise(() => mkdir(path.join(test.directory, "packages", "opencode"), { recursive: true }))
+
+        const current = yield* withSession({ title: "current" }).pipe(
+          provideInstance(path.join(test.directory, "packages", "opencode")),
+        )
+
+        const ids = (yield* SessionNs.Service.use((session) =>
+          session.list({ directory: path.join(test.directory, "packages", "opencode").replaceAll("\\", "/") }),
+        )).map((session) => session.id)
+        expect(ids).toContain(current.id)
+      }),
+    { git: true },
+  )
+
   it.instance(
     "filters by directory when directory is provided",
     () =>
@@ -95,6 +123,35 @@ describe("session.list", () => {
     { git: true },
   )
 
+  it.instance(
+    "matches legacy slash-stored directory rows on Windows",
+    () =>
+      Effect.gen(function* () {
+        if (process.platform !== "win32") return
+        const test = yield* TestInstance
+        yield* Effect.promise(() => mkdir(path.join(test.directory, "packages", "opencode", "src"), { recursive: true }))
+
+        const currentDir = path.join(test.directory, "packages", "opencode", "src")
+        const current = yield* withSession({ title: "legacy-current" }).pipe(provideInstance(currentDir))
+
+        yield* Effect.sync(() =>
+          Database.use((db) =>
+            db
+              .update(SessionTable)
+              .set({ path: null, directory: currentDir.replaceAll("\\", "/") })
+              .where(eq(SessionTable.id, current.id))
+              .run(),
+          ),
+        )
+
+        const ids = (yield* SessionNs.Service.use((session) =>
+          session.list({ directory: currentDir, path: "packages/opencode/src" }),
+        )).map((session) => session.id)
+        expect(ids).toContain(current.id)
+      }),
+    { git: true },
+  )
+
   it.instance(
     "filters by path and ignores directory when path is provided",
     () =>