diff --git a/NAPS2.Lib.Tests/Automation/CommandLineIntegrationTests.cs b/NAPS2.Lib.Tests/Automation/CommandLineIntegrationTests.cs
index bf8e8bb26c..bf6ef1e794 100644
--- a/NAPS2.Lib.Tests/Automation/CommandLineIntegrationTests.cs
+++ b/NAPS2.Lib.Tests/Automation/CommandLineIntegrationTests.cs
@@ -282,6 +282,150 @@ await _automationHelper.RunCommand(
         AssertRecoveryCleanedUp();
     }
 
+    [Fact]
+    public async Task ExistingFile_NoOverwrite_SplitWithPlaceholder()
+    {
+        var path = $"{FolderPath}/test$(n).pdf";
+        await _automationHelper.RunCommand(
+            new AutomatedScanningOptions
+            {
+                OutputPath = path,
+                ProfileName = string.Empty,
+                Split = true,
+                Verbose = true
+            },
+            new[] { Image1, Image2, Image3 });
+        await _automationHelper.WithContainer(container =>
+            {
+                var profileManager = container.Resolve<IProfileManager>();
+                profileManager.Profiles.Remove(profileManager.Profiles.Where(p => p.IsDefault).First());
+            }).RunCommand(
+                new AutomatedScanningOptions
+                {
+                    OutputPath = path,
+                    ProfileName = string.Empty,
+                    Split = true,
+                    Verbose = true
+                },
+                new[] { Image1, Image2, Image3 });
+        PdfAsserts.AssertImages($"{FolderPath}/test1.pdf", Image1);
+        PdfAsserts.AssertImages($"{FolderPath}/test2.pdf", Image2);
+        PdfAsserts.AssertImages($"{FolderPath}/test3.pdf", Image3);
+        Assert.True(File.Exists($"{FolderPath}/test4.pdf"));
+        Assert.True(File.Exists($"{FolderPath}/test5.pdf"));
+        Assert.True(File.Exists($"{FolderPath}/test6.pdf"));
+        AssertRecoveryCleanedUp();
+    }
+
+    [Fact]
+    public async Task ExistingFile_ForceOverwrite_SplitWithPlaceholder()
+    {
+        var path = $"{FolderPath}/test$(n).pdf";
+        await _automationHelper.RunCommand(
+            new AutomatedScanningOptions
+            {
+                OutputPath = path,
+                ForceOverwrite = true,
+                ProfileName = string.Empty,
+                Split = true,
+                Verbose = true
+            },
+            new[] { Image1, Image2, Image3 });
+        await _automationHelper.WithContainer(container =>
+            {
+                var profileManager = container.Resolve<IProfileManager>();
+                profileManager.Profiles.Remove(profileManager.Profiles.Where(p => p.IsDefault).First());
+            }).RunCommand(
+                new AutomatedScanningOptions
+                {
+                    OutputPath = path,
+                    ForceOverwrite = true,
+                    ProfileName = string.Empty,
+                    Split = true,
+                    Verbose = true
+                },
+                new[] { Image1, Image2, Image3 });
+        PdfAsserts.AssertImages($"{FolderPath}/test1.pdf", Image1);
+        PdfAsserts.AssertImages($"{FolderPath}/test2.pdf", Image2);
+        PdfAsserts.AssertImages($"{FolderPath}/test3.pdf", Image3);
+        Assert.False(File.Exists($"{FolderPath}/test4.pdf"));
+        Assert.False(File.Exists($"{FolderPath}/test5.pdf"));
+        Assert.False(File.Exists($"{FolderPath}/test6.pdf"));
+        AssertRecoveryCleanedUp();
+    }
+
+    [Fact]
+    public async Task ExistingFile_NoOverwrite_SplitWithNoPlaceholder()
+    {
+        var path = $"{FolderPath}/test.pdf";
+        await _automationHelper.RunCommand(
+            new AutomatedScanningOptions
+            {
+                OutputPath = path,
+                ProfileName = string.Empty,
+                Split = true,
+                Verbose = true
+            },
+            new[] { Image1, Image2, Image3 });
+        await _automationHelper.WithContainer(container =>
+            {
+                var profileManager = container.Resolve<IProfileManager>();
+                profileManager.Profiles.Remove(profileManager.Profiles.Where(p => p.IsDefault).First());
+            }).RunCommand(
+                new AutomatedScanningOptions
+                {
+                    OutputPath = path,
+                    ProfileName = string.Empty,
+                    Split = true,
+                    Verbose = true
+                },
+                new[] { Image1, Image2, Image3 });
+        PdfAsserts.AssertPageCount(1, $"{FolderPath}/test.1.pdf");
+        PdfAsserts.AssertPageCount(1, $"{FolderPath}/test.2.pdf");
+        PdfAsserts.AssertPageCount(1, $"{FolderPath}/test.3.pdf");
+        Assert.True(File.Exists($"{FolderPath}/test.4.pdf"));
+        Assert.True(File.Exists($"{FolderPath}/test.5.pdf"));
+        Assert.True(File.Exists($"{FolderPath}/test.6.pdf"));
+        AssertRecoveryCleanedUp();
+    }
+
+    [Fact]
+    public async Task ExistingFile_ForceOverwrite_SplitWithNoPlaceholder()
+    {
+        var path = $"{FolderPath}/test.pdf";
+        await _automationHelper.RunCommand(
+            new AutomatedScanningOptions
+            {
+                OutputPath = path,
+                ForceOverwrite = true,
+                ProfileName = string.Empty,
+                Split = true,
+                Verbose = true
+            },
+            new[] { Image1, Image2, Image3 });
+        await _automationHelper.WithContainer(container =>
+            {
+                var profileManager = container.Resolve<IProfileManager>();
+                profileManager.Profiles.Remove(profileManager.Profiles.Where(p => p.IsDefault).First());
+            }).RunCommand(
+                new AutomatedScanningOptions
+                {
+                    OutputPath = path,
+                    ForceOverwrite = true,
+                    ProfileName = string.Empty,
+                    Split = true,
+                    Verbose = true
+                },
+                new[] { Image1, Image2, Image3 });
+        PdfAsserts.AssertPageCount(1, $"{FolderPath}/test.1.pdf");
+        PdfAsserts.AssertPageCount(1, $"{FolderPath}/test.2.pdf");
+        PdfAsserts.AssertPageCount(1, $"{FolderPath}/test.3.pdf");
+        Assert.False(File.Exists($"{FolderPath}/test.4.pdf"));
+        Assert.False(File.Exists($"{FolderPath}/test.5.pdf"));
+        Assert.False(File.Exists($"{FolderPath}/test.6.pdf"));
+        AssertRecoveryCleanedUp();
+    }
+
     [Fact]
     public async Task MultipleImages()
     {
diff --git a/NAPS2.Lib/Automation/AutomatedScanning.cs b/NAPS2.Lib/Automation/AutomatedScanning.cs
index f9f7c389fe..d008044bd9 100644
--- a/NAPS2.Lib/Automation/AutomatedScanning.cs
+++ b/NAPS2.Lib/Automation/AutomatedScanning.cs
@@ -585,7 +585,8 @@ private async Task<bool> DoExportToPdf(string path, bool email)
                 }
             };
             int digits = (int) Math.Floor(Math.Log10(_scanList.Count)) + 1;
-            string actualPath = _placeholders.Substitute(path, true, scanIndex++, _scanList.Count > 1 ? digits : 0);
+            string actualPath = _placeholders.Substitute(path, !_options.ForceOverwrite,
+                scanIndex++, _scanList.Count > 1 ? digits : 0, !_options.ForceOverwrite);
             op.Start(actualPath, _placeholders, fileContents, _config.Get(c => c.PdfSettings), _ocrParams);
             if (!await op.Success)
             {
diff --git a/NAPS2.Lib/Pdf/SavePdfOperation.cs b/NAPS2.Lib/Pdf/SavePdfOperation.cs
index e149b1c3d8..89d15aac5c 100644
--- a/NAPS2.Lib/Pdf/SavePdfOperation.cs
+++ b/NAPS2.Lib/Pdf/SavePdfOperation.cs
@@ -72,8 +72,8 @@ public bool Start(string fileName, Placeholders placeholders, ICollection<Proces
                 int i = 0;
                 foreach (var imagesForFile in imagesByFile)
                 {
-                    var currentFileName = placeholders.Substitute(fileName, true, i, singleFile ? 0 : digits);
-                    // TODO: Overwrite prompt non-single file?
+                    var currentFileName = placeholders.Substitute(fileName, true, i, singleFile ? 0 : digits);
+                    // TODO: Overwrite prompt non-single file?
                     Status.StatusText = string.Format(MiscResources.SavingFormat, Path.GetFileName(currentFileName));
                     InvokeStatusChanged();
                     if (singleFile && IsFileInUse(currentFileName, out var ex))
diff --git a/NAPS2.Sdk/ImportExport/Placeholders.cs b/NAPS2.Sdk/ImportExport/Placeholders.cs
index b0f82bf2a0..be54902435 100644
--- a/NAPS2.Sdk/ImportExport/Placeholders.cs
+++ b/NAPS2.Sdk/ImportExport/Placeholders.cs
@@ -46,21 +46,22 @@ internal abstract class Placeholders
     /// <param name="incrementIfExists">Whether to use an auto-incrementing file number to make the file name unique.</param>
     /// <param name="numberSkip">The file number will be at least one bigger than this value.</param>
     /// <param name="autoNumberDigits">The minimum number of digits in the file number. Only has an effect if the path does not contain a numeric placeholder like $(n) or $(nnn).</param>
+    /// <param name="incrementPlaceholderIfExists">Whether to increment the placeholder number to make the file name unique.</param>
     /// <returns>The file path with substitutions.</returns>
     [return: NotNullIfNotNull("filePath")]
     public abstract string? Substitute(string? filePath, bool incrementIfExists = true, int numberSkip = 0,
-        int autoNumberDigits = 0);
+        int autoNumberDigits = 0, bool incrementPlaceholderIfExists = true);
 
     public class StubPlaceholders : Placeholders
     {
         public override string? Substitute(string? filePath, bool incrementIfExists = true, int numberSkip = 0,
-            int autoNumberDigits = 0) => filePath;
+            int autoNumberDigits = 0, bool incrementPlaceholderIfExists = true) => filePath;
     }
 
     public class EnvironmentPlaceholders : Placeholders
     {
         public override string? Substitute(string? filePath, bool incrementIfExists = true, int numberSkip = 0,
-            int autoNumberDigits = 0)
+            int autoNumberDigits = 0, bool incrementPlaceholderIfExists = true)
         {
             if (filePath == null) return null;
             return Environment.ExpandEnvironmentVariables(filePath);
@@ -99,7 +100,7 @@ public DefaultPlaceholders(DateTime? dateTimeOverride = null)
 
         [return: NotNullIfNotNull("filePath")]
         public override string? Substitute(string? filePath, bool incrementIfExists = true, int numberSkip = 0,
-            int autoNumberDigits = 0)
+            int autoNumberDigits = 0, bool incrementPlaceholderIfExists = true)
         {
             if (filePath == null)
             {
@@ -116,7 +117,7 @@ public DefaultPlaceholders(DateTime? dateTimeOverride = null)
             if (match.Success)
             {
                 result = NumberPlaceholderPattern.Replace(result, "");
-                result = SubstituteNumber(result, match.Index, match.Length - 3, numberSkip, true);
+                result = SubstituteNumber(result, match.Index, match.Length - 3, numberSkip, incrementPlaceholderIfExists);
             }
             else if (autoNumberDigits > 0)
             {