diff --git a/subprojects/core/src/testFixtures/groovy/org/gradle/cache/internal/DefaultFileLockManagerTestHelper.groovy b/subprojects/core/src/testFixtures/groovy/org/gradle/cache/internal/DefaultFileLockManagerTestHelper.groovy
index 189660d2060c..d213cf585a26 100644
--- a/subprojects/core/src/testFixtures/groovy/org/gradle/cache/internal/DefaultFileLockManagerTestHelper.groovy
+++ b/subprojects/core/src/testFixtures/groovy/org/gradle/cache/internal/DefaultFileLockManagerTestHelper.groovy
@@ -61,6 +61,18 @@ abstract class DefaultFileLockManagerTestHelper {
         }, new NoOpFileLockContentionHandler())
     }
 
+    static DefaultFileLockManager createDefaultFileLockManager(int timeout) {
+        new DefaultFileLockManager(new ProcessMetaDataProvider() {
+            String getProcessIdentifier() {
+                return "pid"
+            }
+
+            String getProcessDisplayName() {
+                return "process"
+            }
+        }, timeout, new NoOpFileLockContentionHandler())
+    }
+
     static FileLock createDefaultFileLock(File file, FileLockManager.LockMode mode = FileLockManager.LockMode.Exclusive, DefaultFileLockManager manager = createDefaultFileLockManager()) {
         manager.lock(file, LockOptionsBuilder.mode(mode), "test lock")
     }
diff --git a/subprojects/persistent-cache/src/integTest/groovy/org/gradle/cache/internal/FixedSharedModeCrossProcessCacheAccessIntegrationTest.groovy b/subprojects/persistent-cache/src/integTest/groovy/org/gradle/cache/internal/FixedSharedModeCrossProcessCacheAccessIntegrationTest.groovy
new file mode 100644
index 000000000000..cf5922174ef5
--- /dev/null
+++ b/subprojects/persistent-cache/src/integTest/groovy/org/gradle/cache/internal/FixedSharedModeCrossProcessCacheAccessIntegrationTest.groovy
@@ -0,0 +1,99 @@
+/*
+ * Copyright 2017 the original author or authors.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *      http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package org.gradle.cache.internal
+
+import org.gradle.cache.FileLock
+import org.gradle.cache.FileLockManager
+import org.gradle.cache.internal.filelock.LockOptionsBuilder
+import org.gradle.integtests.fixtures.AbstractIntegrationSpec
+import spock.lang.Issue
+import spock.lang.Subject
+
+import static org.gradle.test.fixtures.ConcurrentTestUtil.poll
+
+@Subject(FixedSharedModeCrossProcessCacheAccess)
+class FixedSharedModeCrossProcessCacheAccessIntegrationTest extends AbstractIntegrationSpec {
+
+    @Issue("https://github.com/gradle/gradle/issues/2737")
+    def "parallel initialization attempt of a shared cache does not timeout one of the processes"() {
+        given:
+        executer.requireOwnGradleUserHomeDir().withDaemonBaseDir(file("daemon")).requireDaemon()
+        buildFile << """
+            task doWork(type: WorkerTask)
+            
+            class WorkerTask extends DefaultTask {         
+                @javax.inject.Inject
+                WorkerExecutor getWorkerExecutor() { throw new UnsupportedOperationException() }
+                
+                @TaskAction
+                void doWork() {
+                    workerExecutor.submit(TestRunnable) { WorkerConfiguration config ->
+                        config.isolationMode = IsolationMode.PROCESS
+                    }
+                    new File("started").createNewFile()
+                    while (!new File("finished").exists()) { Thread.sleep(100) }
+                }
+            }
+            class TestRunnable implements Runnable { void run() { } }
+        """
+
+        when:
+        //start a build with a IsolationMode.PROCESS worker that will initialize the worker classpath cache and wait until the cache was initialized
+        def build = executer.withTasks("doWork").start()
+        poll {
+            assert file("started").exists()
+        }
+
+        //simulate another "build" that tries to initialize the cache as well before recognizing that it has been done already
+        def cacheAccess = simulateAnotherInitializationOfAlreadyInitializedWorkerClasspathCache()
+        cacheAccess.open()
+        file("finished").createFile()
+        build.waitForFinish()
+
+        then:
+        noExceptionThrown()
+
+        cleanup:
+        cacheAccess?.close()
+    }
+
+    /**
+     * This setups a {@link FixedSharedModeCrossProcessCacheAccess} that does initially not see that the cache is already initialised
+     * (or in the process of being initialised). This simulates a situation, where two processes happen to find a the cache in an empty state
+     * simultaneously. Then the the second one, attempting to initialize the cache, will fail to obtain an exclusive lock on the cache. Instead
+     * of failing, it should recheck if initialization was performed by calling {@link CacheInitializationAction#requiresInitialization(org.gradle.cache.FileLock)}
+     * again. This is simulated here by an requiresInitialization() implementation that returns false after a number of calls to itself.
+     */
+    private simulateAnotherInitializationOfAlreadyInitializedWorkerClasspathCache() {
+        def cacheDir = file("user-home/caches/${distribution.version.version}/workerMain")
+        def countingInitAction = new CacheInitializationAction() {
+            def count = 0
+
+            boolean requiresInitialization(FileLock fileLock) {
+                assert fileLock != null
+                count++
+                println "Checking initialized $count"
+                return count < 4
+            }
+
+            void initialize(FileLock fileLock) {}
+        }
+        def lockOptions = LockOptionsBuilder.mode(FileLockManager.LockMode.Shared)
+        def lockManager1 = DefaultFileLockManagerTestHelper.createDefaultFileLockManager(100)
+        new FixedSharedModeCrossProcessCacheAccess("<cache>", cacheDir, lockOptions, lockManager1, countingInitAction, {}, {})
+    }
+}
diff --git a/subprojects/persistent-cache/src/main/java/org/gradle/cache/internal/FixedSharedModeCrossProcessCacheAccess.java b/subprojects/persistent-cache/src/main/java/org/gradle/cache/internal/FixedSharedModeCrossProcessCacheAccess.java
index 27de562fa1b5..5e1ba364469e 100644
--- a/subprojects/persistent-cache/src/main/java/org/gradle/cache/internal/FixedSharedModeCrossProcessCacheAccess.java
+++ b/subprojects/persistent-cache/src/main/java/org/gradle/cache/internal/FixedSharedModeCrossProcessCacheAccess.java
@@ -64,27 +64,36 @@ public void open() {
         try {
             boolean rebuild = initializationAction.requiresInitialization(fileLock);
             if (rebuild) {
+                Exception latestException = null;
                 for (int tries = 0; rebuild && tries < 3; tries++) {
                     fileLock.close();
                     fileLock = null;
-                    final FileLock exclusiveLock = lockManager.lock(lockTarget, lockOptions.withMode(Exclusive), cacheDisplayName);
+                    FileLock exclusiveLock = null;
                     try {
-                        rebuild = initializationAction.requiresInitialization(exclusiveLock);
-                        if (rebuild) {
+                        exclusiveLock = lockManager.lock(lockTarget, lockOptions.withMode(Exclusive), cacheDisplayName);
+                    } catch (Exception e) {
+                        // acquiring the exclusive lock can fail in the rare case where another process is just doing or has just done the cache initialization
+                        latestException = e;
+                    }
+                    try {
+                        if (exclusiveLock != null) {
+                            final FileLock acquiredExclusiveLock = exclusiveLock;
                             exclusiveLock.writeFile(new Runnable() {
                                 public void run() {
-                                    initializationAction.initialize(exclusiveLock);
+                                    initializationAction.initialize(acquiredExclusiveLock);
                                 }
                             });
                         }
                     } finally {
-                        exclusiveLock.close();
+                        if (exclusiveLock != null) {
+                            exclusiveLock.close();
+                        }
                     }
                     fileLock = lockManager.lock(lockTarget, lockOptions, cacheDisplayName);
                     rebuild = initializationAction.requiresInitialization(fileLock);
                 }
                 if (rebuild) {
-                    throw new CacheOpenException(String.format("Failed to initialize %s", cacheDisplayName));
+                    throw new CacheOpenException(String.format("Failed to initialize %s", cacheDisplayName), latestException);
                 }
             }
             onOpenAction.execute(fileLock);