diff --git a/.changeset/fix-parse-git-status.md b/.changeset/fix-parse-git-status.md
new file mode 100644
index 0000000000..ef991cf78e
--- /dev/null
+++ b/.changeset/fix-parse-git-status.md
@@ -0,0 +1,9 @@
+---
+"e2b": patch
+"@e2b/python-sdk": patch
+---
+
+fix(git): prevent crash on malformed branch lines and false detached HEAD detection
+
+- Use `split("...", 1)` / `indexOf("...")` to avoid `ValueError` / incorrect destructuring when the branch line contains multiple `...` sequences (#1371)
+- Remove overly broad `"detached" in raw_branch` / `rawBranch.includes('detached')` check that misidentified branches with "detached" in their name as detached HEAD (#1373)
diff --git a/packages/js-sdk/src/sandbox/git/utils.ts b/packages/js-sdk/src/sandbox/git/utils.ts
index 6df7fbc888..2964448074 100644
--- a/packages/js-sdk/src/sandbox/git/utils.ts
+++ b/packages/js-sdk/src/sandbox/git/utils.ts
@@ -381,14 +381,14 @@ export function parseGitStatus(output: string): GitStatus {
       aheadStart === -1 ? undefined : branchInfo.slice(aheadStart + 2, -1)
     const normalizedBranch = normalizeBranchName(branchPart)
     const rawBranch = branchPart
-    const isDetached =
-      rawBranch.startsWith('HEAD (detached at ') ||
-      rawBranch.includes('detached')
+    const isDetached = rawBranch.startsWith('HEAD (detached at ')
 
     if (isDetached || normalizedBranch.startsWith('HEAD')) {
       detached = true
     } else if (normalizedBranch.includes('...')) {
-      const [branch, upstreamBranch] = normalizedBranch.split('...')
+      const idx = normalizedBranch.indexOf('...')
+      const branch = normalizedBranch.slice(0, idx)
+      const upstreamBranch = normalizedBranch.slice(idx + 3)
       currentBranch = branch || undefined
       upstream = upstreamBranch || undefined
     } else {
diff --git a/packages/js-sdk/tests/sandbox/git/parseGitStatus.test.ts b/packages/js-sdk/tests/sandbox/git/parseGitStatus.test.ts
new file mode 100644
index 0000000000..ef885976ee
--- /dev/null
+++ b/packages/js-sdk/tests/sandbox/git/parseGitStatus.test.ts
@@ -0,0 +1,80 @@
+import { describe, expect, test } from 'vitest'
+
+import { parseGitStatus } from '../../../src/sandbox/git/utils.js'
+
+describe('parseGitStatus', () => {
+    test('malformed branch line with multiple "..." does not crash (issue #1371)', () => {
+        const output = '## feat...v2...origin/feat...v2\n'
+        // Should not throw; exact parsing is best-effort
+        const status = parseGitStatus(output)
+        expect(status.currentBranch).toBeDefined()
+        expect(status.detached).toBe(false)
+    })
+
+    test('upstream branch containing "detached" is not misidentified (issue #1373)', () => {
+        const output = '## my-branch...origin/detached-work\n'
+        const status = parseGitStatus(output)
+        expect(status.currentBranch).toBe('my-branch')
+        expect(status.upstream).toBe('origin/detached-work')
+        expect(status.detached).toBe(false)
+    })
+
+    test('branch literally named "detached" is not treated as detached HEAD', () => {
+        const output = '## detached\n'
+        const status = parseGitStatus(output)
+        expect(status.currentBranch).toBe('detached')
+        expect(status.detached).toBe(false)
+    })
+
+    test('real detached HEAD is still detected', () => {
+        const output = '## HEAD (detached at abc1234)\n'
+        const status = parseGitStatus(output)
+        expect(status.detached).toBe(true)
+    })
+
+    test('branch name containing "detached" substring is not misidentified', () => {
+        const output = '## fix-detached-bug...origin/fix-detached-bug\n'
+        const status = parseGitStatus(output)
+        expect(status.currentBranch).toBe('fix-detached-bug')
+        expect(status.upstream).toBe('origin/fix-detached-bug')
+        expect(status.detached).toBe(false)
+    })
+
+    test('no commits yet parses as branch, not detached', () => {
+        const output = '## No commits yet on main\n'
+        const status = parseGitStatus(output)
+        expect(status.currentBranch).toBe('main')
+        expect(status.detached).toBe(false)
+    })
+
+    test('HEAD (no branch) is treated as detached', () => {
+        const output = '## HEAD (no branch)\n'
+        const status = parseGitStatus(output)
+        expect(status.detached).toBe(true)
+    })
+
+    test('simple branch without upstream', () => {
+        const output = '## feature-branch\n'
+        const status = parseGitStatus(output)
+        expect(status.currentBranch).toBe('feature-branch')
+        expect(status.upstream).toBeUndefined()
+        expect(status.detached).toBe(false)
+    })
+
+    test('empty output returns clean status', () => {
+        const status = parseGitStatus('')
+        expect(status.currentBranch).toBeUndefined()
+        expect(status.detached).toBe(false)
+        expect(status.fileStatus).toEqual([])
+    })
+
+    test('normal branch with upstream parses correctly', () => {
+        const output = '## main...origin/main [ahead 1, behind 2]\n'
+        const status = parseGitStatus(output)
+        expect(status.currentBranch).toBe('main')
+        expect(status.upstream).toBe('origin/main')
+        expect(status.ahead).toBe(1)
+        expect(status.behind).toBe(2)
+        expect(status.detached).toBe(false)
+    })
+})
diff --git a/packages/python-sdk/e2b/sandbox/_git/parse.py b/packages/python-sdk/e2b/sandbox/_git/parse.py
index e6cea693af..a8ad3bbf00 100644
--- a/packages/python-sdk/e2b/sandbox/_git/parse.py
+++ b/packages/python-sdk/e2b/sandbox/_git/parse.py
@@ -125,14 +125,12 @@ def parse_git_status(output: str) -> GitStatus:
         ahead_part = None if ahead_start == -1 else branch_info[ahead_start + 2 : -1]
         normalized_branch = _normalize_branch_name(branch_part)
         raw_branch = branch_part
-        is_detached = raw_branch.startswith("HEAD (detached at ") or (
-            "detached" in raw_branch
-        )
+        is_detached = raw_branch.startswith("HEAD (detached at ")
 
         if is_detached or normalized_branch.startswith("HEAD"):
             detached = True
         elif "..." in normalized_branch:
-            branch, upstream_branch = normalized_branch.split("...")
+            branch, upstream_branch = normalized_branch.split("...", 1)
             current_branch = branch or None
             upstream = upstream_branch or None
         else:
diff --git a/packages/python-sdk/tests/test_parse_git_status.py b/packages/python-sdk/tests/test_parse_git_status.py
new file mode 100644
index 0000000000..855957aaf1
--- /dev/null
+++ b/packages/python-sdk/tests/test_parse_git_status.py
@@ -0,0 +1,88 @@
+from e2b.sandbox._git.parse import parse_git_status
+
+
+def test_split_does_not_crash_with_extra_dots():
+    """Malformed branch lines with multiple '...' should not crash (issue #1371)."""
+    output = "## feat...v2...origin/feat...v2\n"
+    # Should not raise ValueError; exact parsing is best-effort
+    status = parse_git_status(output)
+    assert status.current_branch is not None
+    assert status.detached is False
+
+
+def test_upstream_branch_containing_detached():
+    """Branches tracking an upstream with 'detached' in the name should not
+    be misidentified as detached HEAD (issue #1373)."""
+    output = "## my-branch...origin/detached-work\n"
+    status = parse_git_status(output)
+    assert status.current_branch == "my-branch"
+    assert status.upstream == "origin/detached-work"
+    assert status.detached is False
+
+
+def test_branch_named_detached():
+    """A branch literally named 'detached' should not be treated as
+    detached HEAD."""
+    output = "## detached\n"
+    status = parse_git_status(output)
+    assert status.current_branch == "detached"
+    assert status.detached is False
+
+
+def test_actual_detached_head():
+    """Real detached HEAD should still be detected."""
+    output = "## HEAD (detached at abc1234)\n"
+    status = parse_git_status(output)
+    assert status.detached is True
+
+
+def test_branch_name_containing_detached_substring():
+    """Branch names like 'fix-detached-bug' should not be treated as detached."""
+    output = "## fix-detached-bug...origin/fix-detached-bug\n"
+    status = parse_git_status(output)
+    assert status.current_branch == "fix-detached-bug"
+    assert status.upstream == "origin/fix-detached-bug"
+    assert status.detached is False
+
+
+def test_no_commits_yet():
+    """'No commits yet on main' should parse as branch 'main', not detached."""
+    output = "## No commits yet on main\n"
+    status = parse_git_status(output)
+    assert status.current_branch == "main"
+    assert status.detached is False
+
+
+def test_head_no_branch():
+    """'HEAD (no branch)' should be treated as detached."""
+    output = "## HEAD (no branch)\n"
+    status = parse_git_status(output)
+    assert status.detached is True
+
+
+def test_simple_branch_no_upstream():
+    """A branch with no upstream tracking should parse correctly."""
+    output = "## feature-branch\n"
+    status = parse_git_status(output)
+    assert status.current_branch == "feature-branch"
+    assert status.upstream is None
+    assert status.detached is False
+
+
+def test_empty_output():
+    """Empty output should return a clean status."""
+    status = parse_git_status("")
+    assert status.current_branch is None
+    assert status.detached is False
+    assert status.file_status == []
+
+
+def test_normal_branch_with_upstream():
+    """Normal branch tracking upstream should parse correctly."""
+    output = "## main...origin/main [ahead 1, behind 2]\n"
+    status = parse_git_status(output)
+    assert status.current_branch == "main"
+    assert status.upstream == "origin/main"
+    assert status.ahead == 1
+    assert status.behind == 2
+    assert status.detached is False