diff --git a/packages/server/__snapshots__/5_screenshots_spec.js b/packages/server/__snapshots__/5_screenshots_spec.js
index 123a64036d63..e9fcb36a960f 100644
--- a/packages/server/__snapshots__/5_screenshots_spec.js
+++ b/packages/server/__snapshots__/5_screenshots_spec.js
@@ -147,11 +147,11 @@ Because this error occurred during a \`after each\` hook we are skipping the rem
   -  /XXX/XXX/XXX/cypress/screenshots/screenshots_spec.js/taking screenshots -- reall     (1000x660)
      y long test title aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa               
      aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa               
-     aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa.png                           
+     aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa.png                                        
   -  /XXX/XXX/XXX/cypress/screenshots/screenshots_spec.js/taking screenshots -- reall     (1000x660)
      y long test title aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa               
      aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa               
-     aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa (1).png                           
+     aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa (1).png                                        
 
 
   (Video)
diff --git a/packages/server/lib/screenshots.js b/packages/server/lib/screenshots.js
index f149731d5798..99489e3b37ed 100644
--- a/packages/server/lib/screenshots.js
+++ b/packages/server/lib/screenshots.js
@@ -23,7 +23,7 @@ let __ID__ = null
 // errors are encountered, `maxSafeBytes` will be decremented to at most `MIN_PREFIX_BYTES`, at
 // which point the latest ENAMTOOLONG error will be emitted.
 // @see https://en.wikipedia.org/wiki/Comparison_of_file_systems#Limits
-let maxSafeBytes = 255
+let maxSafeBytes = Number(process.env.CYPRESS_MAX_SAFE_FILENAME_BYTES) || 254
 const MIN_PREFIX_BYTES = 64
 
 // TODO: when we parallelize these builds we'll need
diff --git a/packages/server/test/support/helpers/e2e.ts b/packages/server/test/support/helpers/e2e.ts
index 2630569b8dc2..45098c044214 100644
--- a/packages/server/test/support/helpers/e2e.ts
+++ b/packages/server/test/support/helpers/e2e.ts
@@ -697,6 +697,8 @@ const e2e = {
           LINES: 24,
         })
         .defaults({
+          // match CircleCI's filesystem limits, so screenshot names in snapshots match
+          CYPRESS_MAX_SAFE_FILENAME_BYTES: 242,
           FAKE_CWD_PATH: '/XXX/XXX/XXX',
           DEBUG_COLORS: '1',
           // prevent any Compression progress
diff --git a/packages/server/test/unit/screenshots_spec.js b/packages/server/test/unit/screenshots_spec.js
index 8864bc5fd655..ef193f0ed030 100644
--- a/packages/server/test/unit/screenshots_spec.js
+++ b/packages/server/test/unit/screenshots_spec.js
@@ -577,6 +577,10 @@ describe('lib/screenshots', () => {
   })
 
   context('.getPath', () => {
+    beforeEach(() => {
+      sinon.stub(fs, 'outputFileAsync').resolves()
+    })
+
     it('concats spec name, screenshotsFolder, and name', () => {
       return screenshots.getPath({
         specName: 'examples/user/list.js',
@@ -624,7 +628,7 @@ describe('lib/screenshots', () => {
         titles: [
           'WMED: [STORY] Тестовые сценарии для CI',
           'Сценарии:',
-          'Сценарий 2: Создание обращения, создание медзаписи, привязка обращения к медзаписи',
+          'Сценарий 2: Создание обращения, создание медзаписи, привязкапривязка обращения к медзаписи',
           '- Сценарий 2',
         ],
         testFailure: true,
@@ -636,6 +640,34 @@ describe('lib/screenshots', () => {
       expect(Buffer.from(basename).byteLength).to.be.lessThan(255)
     })
 
+    it('reacts to ENAMETOOLONG errors and tries to shorten the filename', async () => {
+      const err = new Error('enametoolong')
+
+      err.code = 'ENAMETOOLONG'
+
+      _.times(50, (i) => fs.outputFileAsync.onCall(i).rejects(err))
+
+      const fullPath = await screenshots.getPath({
+        specName: 'foo.js',
+        name: 'a'.repeat(256),
+      }, 'png', '/tmp')
+
+      expect(path.basename(fullPath)).to.have.length(204)
+    })
+
+    it('rejects with ENAMETOOLONG errors if name goes below MIN_PREFIX_LENGTH', async () => {
+      const err = new Error('enametoolong')
+
+      err.code = 'ENAMETOOLONG'
+
+      _.times(150, (i) => fs.outputFileAsync.onCall(i).rejects(err))
+
+      await expect(screenshots.getPath({
+        specName: 'foo.js',
+        name: 'a'.repeat(256),
+      }, 'png', '/tmp')).to.be.rejectedWith(err)
+    })
+
     _.each([Infinity, 0 / 0, [], {}, 1, false], (value) => {
       it(`doesn't err and stringifies non-string test title: ${value}`, () => {
         return screenshots.getPath({