diff --git a/CHANGELOG.md b/CHANGELOG.md
index ead6682da12..506d9cd7c3d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -15,6 +15,7 @@ Docs: https://docs.openclaw.ai
 - Agents/compaction: compare post-compaction token sanity checks against full-session pre-compaction totals and skip the check when token estimation fails, so sessions with large bootstrap context keep real token counts instead of falling back to unknown. (#28347) thanks @efe-arv.
 - Discord/gateway startup: treat plain-text and transient `/gateway/bot` metadata fetch failures as transient startup errors so Discord gateway boot no longer crashes on unhandled rejections. (#44397) Thanks @jalehman.
 - Gateway/session reset: preserve `lastAccountId` and `lastThreadId` across gateway session resets so replies keep routing back to the same account and thread after `/reset`. (#44773) Thanks @Lanfei.
+- Agents/memory bootstrap: load only one root memory file, preferring `MEMORY.md` and using `memory.md` as a fallback, so case-insensitive Docker mounts no longer inject duplicate memory context. (#26054) Thanks @Lanfei.
 
 ## 2026.3.12
 
diff --git a/docs/concepts/system-prompt.md b/docs/concepts/system-prompt.md
index 1a5edfcc6e3..a1d1b482fb2 100644
--- a/docs/concepts/system-prompt.md
+++ b/docs/concepts/system-prompt.md
@@ -59,7 +59,7 @@ Bootstrap files are trimmed and appended under **Project Context** so the model
 - `USER.md`
 - `HEARTBEAT.md`
 - `BOOTSTRAP.md` (only on brand-new workspaces)
-- `MEMORY.md` and/or `memory.md` (when present in the workspace; either or both may be injected)
+- `MEMORY.md` when present, otherwise `memory.md` as a lowercase fallback
 
 All of these files are **injected into the context window** on every turn, which
 means they consume tokens. Keep them concise — especially `MEMORY.md`, which can
diff --git a/docs/reference/token-use.md b/docs/reference/token-use.md
index 9e85c25e687..8493e99f098 100644
--- a/docs/reference/token-use.md
+++ b/docs/reference/token-use.md
@@ -18,7 +18,7 @@ OpenClaw assembles its own system prompt on every run. It includes:
 - Tool list + short descriptions
 - Skills list (only metadata; instructions are loaded on demand with `read`)
 - Self-update instructions
-- Workspace + bootstrap files (`AGENTS.md`, `SOUL.md`, `TOOLS.md`, `IDENTITY.md`, `USER.md`, `HEARTBEAT.md`, `BOOTSTRAP.md` when new, plus `MEMORY.md` and/or `memory.md` when present). Large files are truncated by `agents.defaults.bootstrapMaxChars` (default: 20000), and total bootstrap injection is capped by `agents.defaults.bootstrapTotalMaxChars` (default: 150000). `memory/*.md` files are on-demand via memory tools and are not auto-injected.
+- Workspace + bootstrap files (`AGENTS.md`, `SOUL.md`, `TOOLS.md`, `IDENTITY.md`, `USER.md`, `HEARTBEAT.md`, `BOOTSTRAP.md` when new, plus `MEMORY.md` when present or `memory.md` as a lowercase fallback). Large files are truncated by `agents.defaults.bootstrapMaxChars` (default: 20000), and total bootstrap injection is capped by `agents.defaults.bootstrapTotalMaxChars` (default: 150000). `memory/*.md` files are on-demand via memory tools and are not auto-injected.
 - Time (UTC + user timezone)
 - Reply tags + heartbeat behavior
 - Runtime metadata (host/OS/model/thinking)
diff --git a/src/agents/workspace.ts b/src/agents/workspace.ts
index 830b44504ad..c4f1044a8d9 100644
--- a/src/agents/workspace.ts
+++ b/src/agents/workspace.ts
@@ -458,41 +458,24 @@ export async function ensureAgentWorkspace(params?: {
   };
 }
 
-async function resolveMemoryBootstrapEntries(
+async function resolveMemoryBootstrapEntry(
   resolvedDir: string,
-): Promise<Array<{ name: WorkspaceBootstrapFileName; filePath: string }>> {
-  const candidates: WorkspaceBootstrapFileName[] = [
-    DEFAULT_MEMORY_FILENAME,
-    DEFAULT_MEMORY_ALT_FILENAME,
-  ];
-  const entries: Array<{ name: WorkspaceBootstrapFileName; filePath: string }> = [];
-  for (const name of candidates) {
+): Promise<{ name: WorkspaceBootstrapFileName; filePath: string } | null> {
+  // Prefer MEMORY.md; fall back to memory.md only when absent.
+  // Checking both and deduplicating via realpath is unreliable on case-insensitive
+  // file systems mounted in Docker (e.g. macOS volumes), where both names pass
+  // fs.access() but realpath does not normalise case through the mount layer,
+  // causing the same content to be injected twice and wasting tokens.
+  for (const name of [DEFAULT_MEMORY_FILENAME, DEFAULT_MEMORY_ALT_FILENAME] as const) {
     const filePath = path.join(resolvedDir, name);
     try {
       await fs.access(filePath);
-      entries.push({ name, filePath });
+      return { name, filePath };
     } catch {
-      // optional
+      // try next candidate
     }
   }
-  if (entries.length <= 1) {
-    return entries;
-  }
-
-  const seen = new Set<string>();
-  const deduped: Array<{ name: WorkspaceBootstrapFileName; filePath: string }> = [];
-  for (const entry of entries) {
-    let key = entry.filePath;
-    try {
-      key = await fs.realpath(entry.filePath);
-    } catch {}
-    if (seen.has(key)) {
-      continue;
-    }
-    seen.add(key);
-    deduped.push(entry);
-  }
-  return deduped;
+  return null;
 }
 
 export async function loadWorkspaceBootstrapFiles(dir: string): Promise<WorkspaceBootstrapFile[]> {
@@ -532,7 +515,10 @@ export async function loadWorkspaceBootstrapFiles(dir: string): Promise<Workspac
     },
   ];
 
-  entries.push(...(await resolveMemoryBootstrapEntries(resolvedDir)));
+  const memoryEntry = await resolveMemoryBootstrapEntry(resolvedDir);
+  if (memoryEntry) {
+    entries.push(memoryEntry);
+  }
 
   const result: WorkspaceBootstrapFile[] = [];
   for (const entry of entries) {