diff --git a/cmd/api/src/daemons/datapipe/cleanup.go b/cmd/api/src/daemons/datapipe/cleanup.go
new file mode 100644
index 0000000000..5b24ec3e61
--- /dev/null
+++ b/cmd/api/src/daemons/datapipe/cleanup.go
@@ -0,0 +1,113 @@
+// Copyright 2024 Specter Ops, Inc.
+//
+// Licensed under the Apache License, Version 2.0
+// 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.
+//
+// SPDX-License-Identifier: Apache-2.0
+
+package datapipe
+
+//go:generate go run go.uber.org/mock/mockgen -copyright_file=../../../../../LICENSE.header -destination=./mocks/cleanup.go -package=mocks . FileOperations
+
+import (
+	"context"
+	"github.com/specterops/bloodhound/log"
+	"os"
+	"path/filepath"
+	"sync"
+)
+
+// FileOperations is an interface for describing filesystem actions. This implementation exists due to deficiencies in
+// the fs package where the fs.FS interface does not support destructive operations like RemoveAll.
+type FileOperations interface {
+	ReadDir(path string) ([]os.DirEntry, error)
+	RemoveAll(path string) error
+}
+
+// osFileOperations is a passthrough implementation of the FileOperations interface that uses the os package
+// functions.
+type osFileOperations struct{}
+
+func NewOSFileOperations() FileOperations {
+	return osFileOperations{}
+}
+
+func (s osFileOperations) ReadDir(path string) ([]os.DirEntry, error) {
+	return os.ReadDir(path)
+}
+
+func (s osFileOperations) RemoveAll(path string) error {
+	return os.RemoveAll(path)
+}
+
+// OrphanFileSweeper is a file cleanup utility that allows only one goroutine to attempt file cleanup at a time.
+type OrphanFileSweeper struct {
+	lock                  *sync.Mutex
+	fileOps               FileOperations
+	tempDirectoryRootPath string
+}
+
+func NewOrphanFileSweeper(fileOps FileOperations, tempDirectoryRootPath string) *OrphanFileSweeper {
+	return &OrphanFileSweeper{
+		lock:                  &sync.Mutex{},
+		fileOps:               fileOps,
+		tempDirectoryRootPath: tempDirectoryRootPath,
+	}
+}
+
+// Clear takes a context and a list of expected file names. The function will list all directory entries within the
+// configured tempDirectoryRootPath that the sweeper was instantiated with and compare the resulting list against the
+// passed expected file names. The function will then call RemoveAll on each directory entry not found in the expected
+// file name slice.
+func (s *OrphanFileSweeper) Clear(ctx context.Context, expectedFileNames []string) {
+	// Only allow one background thread to run for clearing orphaned data/
+	if !s.lock.TryLock() {
+		return
+	}
+
+	// Release the lock once finished
+	defer s.lock.Unlock()
+
+	if dirEntries, err := s.fileOps.ReadDir(s.tempDirectoryRootPath); err != nil {
+		log.Errorf("Failed reading work directory %s: %v", s.tempDirectoryRootPath, err)
+	} else {
+		numDeleted := 0
+
+		// Remove expected files from the deletion list
+		for _, expectedFileName := range expectedFileNames {
+			for idx, dirEntry := range dirEntries {
+				if expectedFileName == dirEntry.Name() {
+					dirEntries = append(dirEntries[:idx], dirEntries[idx+1:]...)
+				}
+			}
+		}
+
+		for _, orphanedDirEntry := range dirEntries {
+			// Check for context cancellation before each file deletion
+			if ctx.Err() != nil {
+				break
+			}
+
+			fullPath := filepath.Join(s.tempDirectoryRootPath, orphanedDirEntry.Name())
+
+			if err := s.fileOps.RemoveAll(fullPath); err != nil {
+				log.Errorf("Failed removing orphaned file %s: %v", fullPath, err)
+			}
+
+			numDeleted += 1
+		}
+
+		if numDeleted > 0 {
+			log.Infof("Finished removing %d orphaned ingest files", numDeleted)
+		}
+	}
+}
diff --git a/cmd/api/src/daemons/datapipe/cleanup_test.go b/cmd/api/src/daemons/datapipe/cleanup_test.go
new file mode 100644
index 0000000000..7717e5dc0d
--- /dev/null
+++ b/cmd/api/src/daemons/datapipe/cleanup_test.go
@@ -0,0 +1,159 @@
+// Copyright 2024 Specter Ops, Inc.
+//
+// Licensed under the Apache License, Version 2.0
+// 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.
+//
+// SPDX-License-Identifier: Apache-2.0
+
+package datapipe_test
+
+import (
+	"context"
+	"github.com/specterops/bloodhound/src/daemons/datapipe"
+	"github.com/specterops/bloodhound/src/daemons/datapipe/mocks"
+	"go.uber.org/mock/gomock"
+	"io/fs"
+	"os"
+	"path/filepath"
+	"sync"
+	"testing"
+)
+
+type dirEntry struct {
+	name    string
+	isDir   bool
+	mode    fs.FileMode
+	info    fs.FileInfo
+	infoErr error
+}
+
+func (s dirEntry) Name() string {
+	return s.name
+}
+
+func (s dirEntry) IsDir() bool {
+	return s.isDir
+}
+
+func (s dirEntry) Type() fs.FileMode {
+	return s.mode
+}
+
+func (s dirEntry) Info() (fs.FileInfo, error) {
+	return s.info, s.infoErr
+}
+
+func TestOrphanFileSweeper_Clear(t *testing.T) {
+	const workDir = "/fake/work/dir"
+
+	t.Run("Allow Only One Goroutine", func(t *testing.T) {
+		var (
+			mockCtrl       = gomock.NewController(t)
+			mockFileOps    = mocks.NewMockFileOperations(mockCtrl)
+			sweeper        = datapipe.NewOrphanFileSweeper(mockFileOps, workDir)
+			wgCoordination = &sync.WaitGroup{}
+			wgReadDir      = &sync.WaitGroup{}
+		)
+
+		defer mockCtrl.Finish()
+
+		// Prep the wait groups for coordination
+		wgCoordination.Add(1)
+		wgReadDir.Add(1)
+
+		mockFileOps.EXPECT().ReadDir(workDir).DoAndReturn(func(path string) ([]os.DirEntry, error) {
+			// Release the coordination wait group
+			wgCoordination.Done()
+
+			// Block on the readDir wait group
+			wgReadDir.Wait()
+
+			return nil, nil
+		})
+
+		// Launch the clear function in a goroutine. The wait group will cause this call to block
+		go sweeper.Clear(context.Background(), []string{})
+
+		// Wait for the go routine to reach the ReadDir function
+		wgCoordination.Wait()
+
+		// Run the clear function in the current thread context as this should exit without blocking
+		sweeper.Clear(context.Background(), []string{})
+
+		// Release the wait group to complete the test
+		wgReadDir.Done()
+	})
+
+	t.Run("Clear Orphan Files", func(t *testing.T) {
+		var (
+			mockCtrl    = gomock.NewController(t)
+			mockFileOps = mocks.NewMockFileOperations(mockCtrl)
+			sweeper     = datapipe.NewOrphanFileSweeper(mockFileOps, workDir)
+		)
+
+		defer mockCtrl.Finish()
+
+		mockFileOps.EXPECT().ReadDir(workDir).Return([]os.DirEntry{
+			dirEntry{
+				name: "1",
+			},
+		}, nil)
+
+		mockFileOps.EXPECT().RemoveAll(filepath.Join(workDir, "1")).Return(nil)
+
+		sweeper.Clear(context.Background(), []string{})
+	})
+
+	t.Run("Exclude Expected Files", func(t *testing.T) {
+		var (
+			mockCtrl    = gomock.NewController(t)
+			mockFileOps = mocks.NewMockFileOperations(mockCtrl)
+			sweeper     = datapipe.NewOrphanFileSweeper(mockFileOps, workDir)
+		)
+
+		defer mockCtrl.Finish()
+
+		mockFileOps.EXPECT().ReadDir(workDir).Return([]os.DirEntry{
+			dirEntry{
+				name: "1",
+			},
+		}, nil)
+
+		// This one is a negative assertion. Because we're passing in "1" to be excluded the listed dirEntries will be
+		// empty and therefore the sweeper MUST NOT call RemoveAll() on the FileOperations mock. If RemoveAll() is
+		// called then this test MUST fail.
+		sweeper.Clear(context.Background(), []string{"1"})
+	})
+
+	t.Run("Exit on Context Cancellation", func(t *testing.T) {
+		var (
+			mockCtrl    = gomock.NewController(t)
+			mockFileOps = mocks.NewMockFileOperations(mockCtrl)
+			sweeper     = datapipe.NewOrphanFileSweeper(mockFileOps, workDir)
+		)
+
+		defer mockCtrl.Finish()
+
+		mockFileOps.EXPECT().ReadDir(workDir).Return([]os.DirEntry{
+			dirEntry{
+				name: "1",
+			},
+		}, nil)
+
+		// Create a cancellable context and cancel it right away
+		ctx, done := context.WithCancel(context.Background())
+		done()
+
+		// When passed in with the cancelled context the sweeper should not call os.RemoveAll("1")
+		sweeper.Clear(ctx, []string{})
+	})
+}
diff --git a/cmd/api/src/daemons/datapipe/datapipe.go b/cmd/api/src/daemons/datapipe/datapipe.go
index ef2b2e2d71..432e91cc15 100644
--- a/cmd/api/src/daemons/datapipe/datapipe.go
+++ b/cmd/api/src/daemons/datapipe/datapipe.go
@@ -14,16 +14,13 @@
 //
 // SPDX-License-Identifier: Apache-2.0
 
-//go:generate go run go.uber.org/mock/mockgen -copyright_file=../../../../../LICENSE.header -destination=./mocks/mock.go -package=mocks . Tasker
+//go:generate go run go.uber.org/mock/mockgen -copyright_file=../../../../../LICENSE.header -destination=./mocks/tasker.go -package=mocks . Tasker
 package datapipe
 
 import (
 	"context"
 	"errors"
 	"github.com/specterops/bloodhound/src/bootstrap"
-	"os"
-	"path/filepath"
-	"sync"
 	"sync/atomic"
 	"time"
 
@@ -47,15 +44,15 @@ type Tasker interface {
 }
 
 type Daemon struct {
-	db                     database.Database
-	graphdb                graph.Database
-	cache                  cache.Cache
-	cfg                    config.Configuration
-	analysisRequested      *atomic.Bool
-	tickInterval           time.Duration
-	status                 model.DatapipeStatusWrapper
-	ctx                    context.Context
-	clearOrphanedFilesLock *sync.Mutex
+	db                  database.Database
+	graphdb             graph.Database
+	cache               cache.Cache
+	cfg                 config.Configuration
+	analysisRequested   *atomic.Bool
+	tickInterval        time.Duration
+	status              model.DatapipeStatusWrapper
+	ctx                 context.Context
+	orphanedFileSweeper *OrphanFileSweeper
 }
 
 func (s *Daemon) Name() string {
@@ -64,14 +61,14 @@ func (s *Daemon) Name() string {
 
 func NewDaemon(ctx context.Context, cfg config.Configuration, connections bootstrap.DatabaseConnections[*database.BloodhoundDB, *graph.DatabaseSwitch], cache cache.Cache, tickInterval time.Duration) *Daemon {
 	return &Daemon{
-		db:                     connections.RDMS,
-		graphdb:                connections.Graph,
-		cache:                  cache,
-		cfg:                    cfg,
-		ctx:                    ctx,
-		analysisRequested:      &atomic.Bool{},
-		clearOrphanedFilesLock: &sync.Mutex{},
-		tickInterval:           tickInterval,
+		db:                  connections.RDMS,
+		graphdb:             connections.Graph,
+		cache:               cache,
+		cfg:                 cfg,
+		ctx:                 ctx,
+		analysisRequested:   &atomic.Bool{},
+		orphanedFileSweeper: NewOrphanFileSweeper(NewOSFileOperations(), cfg.TempDirectory()),
+		tickInterval:        tickInterval,
 		status: model.DatapipeStatusWrapper{
 			Status:    model.DatapipeStatusIdle,
 			UpdatedAt: time.Now().UTC(),
@@ -105,7 +102,7 @@ func (s *Daemon) analyze() {
 	}
 
 	s.status.Update(model.DatapipeStatusAnalyzing, false)
-	log.LogAndMeasure(log.LevelInfo, "Graph Analysis")()
+	defer log.LogAndMeasure(log.LevelInfo, "Graph Analysis")()
 
 	if err := RunAnalysisOperations(s.ctx, s.db, s.graphdb, s.cfg); err != nil {
 		if errors.Is(err, ErrAnalysisFailed) {
@@ -190,44 +187,15 @@ func (s *Daemon) Stop(ctx context.Context) error {
 }
 
 func (s *Daemon) clearOrphanedData() {
-	// Only allow one background thread to run for clearing orphaned data
-	if !s.clearOrphanedFilesLock.TryLock() {
-		return
-	}
-
-	// Release the lock once finished
-	defer s.clearOrphanedFilesLock.Unlock()
-
-	relativeTmpDir := s.cfg.TempDirectory()
-
-	if orphanFiles, err := os.ReadDir(s.cfg.TempDirectory()); err != nil {
-		log.Errorf("Failed fetching available files: %v", err)
-	} else if ingestTasks, err := s.db.GetAllIngestTasks(); err != nil {
-		log.Errorf("Failed fetching available ingest tasks: %v", err)
+	if ingestTasks, err := s.db.GetAllIngestTasks(); err != nil {
+		log.Errorf("Failed fetching available file upload ingest tasks: %v", err)
 	} else {
-		for _, ingestTask := range ingestTasks {
-			for idx, orphanFile := range orphanFiles {
-				if ingestTask.FileName == filepath.Join(relativeTmpDir, orphanFile.Name()) {
-					orphanFiles = append(orphanFiles[:idx], orphanFiles[idx+1:]...)
-				}
-			}
-		}
+		expectedFiles := make([]string, len(ingestTasks))
 
-		for _, orphanFile := range orphanFiles {
-			fullPath := filepath.Join(relativeTmpDir, orphanFile.Name())
-
-			if err := os.RemoveAll(fullPath); err != nil {
-				log.Errorf("Failed removing file: %s", fullPath)
-			}
-
-			// Check to see if we need to exit after every file deletion
-			if s.ctx.Err() != nil {
-				return
-			}
+		for idx, ingestTask := range ingestTasks {
+			expectedFiles[idx] = ingestTask.FileName
 		}
 
-		if len(orphanFiles) > 0 {
-			log.Infof("Finished removing %d orphaned ingest files", len(orphanFiles))
-		}
+		go s.orphanedFileSweeper.Clear(s.ctx, expectedFiles)
 	}
 }
diff --git a/cmd/api/src/daemons/datapipe/mocks/cleanup.go b/cmd/api/src/daemons/datapipe/mocks/cleanup.go
new file mode 100644
index 0000000000..d7d3b8aa15
--- /dev/null
+++ b/cmd/api/src/daemons/datapipe/mocks/cleanup.go
@@ -0,0 +1,80 @@
+// Copyright 2023 Specter Ops, Inc.
+//
+// Licensed under the Apache License, Version 2.0
+// 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.
+//
+// SPDX-License-Identifier: Apache-2.0
+
+// Code generated by MockGen. DO NOT EDIT.
+// Source: github.com/specterops/bloodhound/src/daemons/datapipe (interfaces: FileOperations)
+
+// Package mocks is a generated GoMock package.
+package mocks
+
+import (
+	fs "io/fs"
+	reflect "reflect"
+
+	gomock "go.uber.org/mock/gomock"
+)
+
+// MockFileOperations is a mock of FileOperations interface.
+type MockFileOperations struct {
+	ctrl     *gomock.Controller
+	recorder *MockFileOperationsMockRecorder
+}
+
+// MockFileOperationsMockRecorder is the mock recorder for MockFileOperations.
+type MockFileOperationsMockRecorder struct {
+	mock *MockFileOperations
+}
+
+// NewMockFileOperations creates a new mock instance.
+func NewMockFileOperations(ctrl *gomock.Controller) *MockFileOperations {
+	mock := &MockFileOperations{ctrl: ctrl}
+	mock.recorder = &MockFileOperationsMockRecorder{mock}
+	return mock
+}
+
+// EXPECT returns an object that allows the caller to indicate expected use.
+func (m *MockFileOperations) EXPECT() *MockFileOperationsMockRecorder {
+	return m.recorder
+}
+
+// ReadDir mocks base method.
+func (m *MockFileOperations) ReadDir(arg0 string) ([]fs.DirEntry, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "ReadDir", arg0)
+	ret0, _ := ret[0].([]fs.DirEntry)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// ReadDir indicates an expected call of ReadDir.
+func (mr *MockFileOperationsMockRecorder) ReadDir(arg0 interface{}) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "ReadDir", reflect.TypeOf((*MockFileOperations)(nil).ReadDir), arg0)
+}
+
+// RemoveAll mocks base method.
+func (m *MockFileOperations) RemoveAll(arg0 string) error {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "RemoveAll", arg0)
+	ret0, _ := ret[0].(error)
+	return ret0
+}
+
+// RemoveAll indicates an expected call of RemoveAll.
+func (mr *MockFileOperationsMockRecorder) RemoveAll(arg0 interface{}) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "RemoveAll", reflect.TypeOf((*MockFileOperations)(nil).RemoveAll), arg0)
+}
diff --git a/cmd/api/src/daemons/datapipe/mocks/mock.go b/cmd/api/src/daemons/datapipe/mocks/tasker.go
similarity index 100%
rename from cmd/api/src/daemons/datapipe/mocks/mock.go
rename to cmd/api/src/daemons/datapipe/mocks/tasker.go