diff --git a/packages/server/src/server/session.ts b/packages/server/src/server/session.ts
index 3aac4667c..46c84e02a 100644
--- a/packages/server/src/server/session.ts
+++ b/packages/server/src/server/session.ts
@@ -5165,20 +5165,35 @@ export class Session {
     const timestamp = new Date().toISOString();
     const directoryName = normalizedCwd.split(/[\\/]/).filter(Boolean).at(-1) ?? normalizedCwd;
     const gitMetadata = detectWorkspaceGitMetadata(normalizedCwd, directoryName);
-    const projectId = await this.projectRegistry.insert({
-      directory: normalizedCwd,
-      displayName: gitMetadata.projectDisplayName,
-      kind: gitMetadata.projectKind,
-      gitRemote: gitMetadata.gitRemote,
-      createdAt: timestamp,
-      updatedAt: timestamp,
-      archivedAt: null,
-    });
+
+    let projectId: number | null = null;
+    if (gitMetadata.gitRemote) {
+      const existingProjects = await this.projectRegistry.list();
+      const matchingProject = existingProjects.find(
+        (p) => p.gitRemote === gitMetadata.gitRemote && !p.archivedAt,
+      );
+      if (matchingProject) {
+        projectId = matchingProject.id;
+      }
+    }
+
+    if (projectId === null) {
+      projectId = await this.projectRegistry.insert({
+        directory: normalizedCwd,
+        displayName: gitMetadata.projectDisplayName,
+        kind: gitMetadata.projectKind,
+        gitRemote: gitMetadata.gitRemote,
+        createdAt: timestamp,
+        updatedAt: timestamp,
+        archivedAt: null,
+      });
+    }
+
     const workspaceId = await this.workspaceRegistry.insert({
       projectId,
       directory: normalizedCwd,
       displayName: gitMetadata.workspaceDisplayName,
-      kind: "checkout",
+      kind: gitMetadata.isWorktree ? "worktree" : "checkout",
       createdAt: timestamp,
       updatedAt: timestamp,
       archivedAt: null,
diff --git a/packages/server/src/server/workspace-git-metadata.ts b/packages/server/src/server/workspace-git-metadata.ts
index e3c3466c6..1af8fd192 100644
--- a/packages/server/src/server/workspace-git-metadata.ts
+++ b/packages/server/src/server/workspace-git-metadata.ts
@@ -6,6 +6,7 @@ export type WorkspaceGitMetadata = {
   projectDisplayName: string;
   workspaceDisplayName: string;
   gitRemote: string | null;
+  isWorktree: boolean;
 };
 
 export function readGitCommand(cwd: string, command: string): string | null {
@@ -66,17 +67,21 @@ export function detectWorkspaceGitMetadata(
       projectDisplayName: directoryName,
       workspaceDisplayName: directoryName,
       gitRemote: null,
+      isWorktree: false,
     };
   }
 
   const gitRemote = readGitCommand(cwd, "git config --get remote.origin.url");
   const githubRepo = gitRemote ? parseGitHubRepoFromRemote(gitRemote) : null;
   const branchName = readGitCommand(cwd, "git symbolic-ref --short HEAD");
+  const gitCommonDir = readGitCommand(cwd, "git rev-parse --git-common-dir");
+  const isWorktree = gitCommonDir !== null && gitDir !== gitCommonDir;
 
   return {
     projectKind: "git",
     projectDisplayName: githubRepo ?? directoryName,
     workspaceDisplayName: branchName ?? directoryName,
     gitRemote,
+    isWorktree,
   };
 }