diff --git a/packages/app/e2e/projects/workspace-new-session.spec.ts b/packages/app/e2e/projects/workspace-new-session.spec.ts
index 18fa46d3299..643aa1212d7 100644
--- a/packages/app/e2e/projects/workspace-new-session.spec.ts
+++ b/packages/app/e2e/projects/workspace-new-session.spec.ts
@@ -70,7 +70,11 @@ async function createSessionFromWorkspace(page: Page, slug: string, text: string
 }
 
 async function sessionDirectory(directory: string, sessionID: string) {
-  const info = await createSdk(directory)
+  // Normalize directory path for consistent comparison on Windows
+  // (convert backslashes to forward slashes and uppercase drive letter)
+  const normalizedDir = directory.replace(/\\/g, "/").replace(/^([a-z]):/, (_, drive) => drive.toUpperCase() + ":")
+
+  const info = await createSdk(normalizedDir)
     .session.get({ sessionID })
     .then((x) => x.data)
     .catch(() => undefined)
diff --git a/packages/opencode/src/session/index.ts b/packages/opencode/src/session/index.ts
index 0879fe87fd3..92e1bf8e27d 100644
--- a/packages/opencode/src/session/index.ts
+++ b/packages/opencode/src/session/index.ts
@@ -39,6 +39,21 @@ export namespace Session {
   const parentTitlePrefix = "New session - "
   const childTitlePrefix = "Child session - "
 
+  /**
+   * Normalize directory path for consistent comparison across platforms.
+   * On Windows, paths can have different representations (e.g., B: vs b:, / vs \).
+   * This function ensures consistent path comparison for session listing.
+   */
+  function normalizeDirectory(dir: string): string {
+    // Normalize backslashes to forward slashes
+    let normalized = dir.replaceAll("\\", "/")
+    // Normalize drive letter to uppercase for case-insensitive comparison on Windows
+    if (process.platform === "win32") {
+      normalized = normalized.replace(/^([a-z]):/, (_, drive) => drive.toUpperCase() + ":")
+    }
+    return normalized
+  }
+
   function createDefaultTitle(isChild = false) {
     return (isChild ? childTitlePrefix : parentTitlePrefix) + new Date().toISOString()
   }
@@ -92,7 +107,7 @@ export namespace Session {
       workspace_id: info.workspaceID,
       parent_id: info.parentID,
       slug: info.slug,
-      directory: info.directory,
+      directory: normalizeDirectory(info.directory),
       title: info.title,
       version: info.version,
       share_url: info.share?.url,
@@ -552,7 +567,10 @@ export namespace Session {
       conditions.push(eq(SessionTable.workspace_id, WorkspaceContext.workspaceID))
     }
     if (input?.directory) {
-      conditions.push(eq(SessionTable.directory, input.directory))
+      // Normalize the directory path to handle Windows path variations
+      // (e.g., B: vs b:, / vs \)
+      const normalizedDir = normalizeDirectory(input.directory)
+      conditions.push(eq(SessionTable.directory, normalizedDir))
     }
     if (input?.roots) {
       conditions.push(isNull(SessionTable.parent_id))
@@ -592,7 +610,10 @@ export namespace Session {
     const conditions: SQL[] = []
 
     if (input?.directory) {
-      conditions.push(eq(SessionTable.directory, input.directory))
+      // Normalize the directory path to handle Windows path variations
+      // (e.g., B: vs b:, / vs \)
+      const normalizedDir = normalizeDirectory(input.directory)
+      conditions.push(eq(SessionTable.directory, normalizedDir))
     }
     if (input?.roots) {
       conditions.push(isNull(SessionTable.parent_id))