diff --git a/Frontmatter.Test/PropertyMergerTests.cs b/Frontmatter.Test/PropertyMergerTests.cs
index 4314c03..200b1a5 100644
--- a/Frontmatter.Test/PropertyMergerTests.cs
+++ b/Frontmatter.Test/PropertyMergerTests.cs
@@ -769,6 +769,6 @@ public void CombineFrontmatter_SingleBlockWithRepeatedListItems_RoundTripsTheLis
 
 		Assert.IsNotNull(frontmatter);
 		CollectionAssert.AreEqual(new object[] { "mix", "wait", "mix" }, (System.Collections.ICollection)frontmatter["steps"]);
-		CollectionAssert.AreEqual(new object[] { "1", "1", "2" }, (System.Collections.ICollection)frontmatter["scores"]);
+		CollectionAssert.AreEqual(new long[] { 1, 1, 2 }, ((System.Collections.IEnumerable)frontmatter["scores"]).Cast<object>().Select(score => Convert.ToInt64(score, System.Globalization.CultureInfo.InvariantCulture)).ToArray());
 	}
 }
diff --git a/Frontmatter.Test/ScalarTypeRoundTripTests.cs b/Frontmatter.Test/ScalarTypeRoundTripTests.cs
new file mode 100644
index 0000000..eff7760
--- /dev/null
+++ b/Frontmatter.Test/ScalarTypeRoundTripTests.cs
@@ -0,0 +1,72 @@
+// Copyright (c) 2023-2026 ktsu-dev contributors
+
+namespace ktsu.Frontmatter.Test;
+
+using System.Collections.Generic;
+
+using Microsoft.VisualStudio.TestTools.UnitTesting;
+
+using YamlDotNet.Serialization;
+
+/// <summary>
+/// Regression tests for #137: a round trip must keep what each scalar means. Quoted strings that look
+/// like other types stay strings, plain scalars keep their types, and nulls stay null.
+/// </summary>
+[TestClass]
+public class ScalarTypeRoundTripTests
+{
+	private static readonly string Nl = Environment.NewLine;
+
+	private static readonly IDeserializer TypedReader = new DeserializerBuilder()
+		.WithAttemptingUnquotedStringTypeDeserialization()
+		.Build();
+
+	private static Dictionary<object, object?> ReadHeader(string document)
+	{
+		string[] parts = document.Split(["---"], 3, StringSplitOptions.None);
+		return TypedReader.Deserialize<Dictionary<object, object?>>(parts[1]);
+	}
+
+	[TestMethod]
+	[DataRow(FrontmatterMergeStrategy.None)]
+	[DataRow(FrontmatterMergeStrategy.Conservative)]
+	public void CombineFrontmatter_QuotedLookalikesNullsAndBooleans_KeepTheirTypes(FrontmatterMergeStrategy strategy)
+	{
+		string input = $"---{Nl}title: \"true\"{Nl}version: \"1.0\"{Nl}zip: \"01234\"{Nl}null_str: \"null\"{Nl}empty:{Nl}draft: false{Nl}count: 3{Nl}---{Nl}body{Nl}";
+
+		string result = Frontmatter.CombineFrontmatter(input, FrontmatterNaming.AsIs, FrontmatterOrder.AsIs, strategy);
+		Dictionary<object, object?> header = ReadHeader(result);
+
+		Assert.AreEqual("true", header["title"], result);
+		Assert.AreEqual("1.0", header["version"], result);
+		Assert.AreEqual("01234", header["zip"], result);
+		Assert.AreEqual("null", header["null_str"], result);
+		Assert.IsTrue(header.TryGetValue("empty", out object? emptyValue), result);
+		Assert.IsNull(emptyValue, result);
+		Assert.IsInstanceOfType<bool>(header["draft"], result);
+		Assert.IsFalse((bool)header["draft"]!, result);
+		Assert.AreEqual(3L, Convert.ToInt64(header["count"], System.Globalization.CultureInfo.InvariantCulture), result);
+		Assert.Contains($"draft: false{Nl}", result);
+	}
+
+	[TestMethod]
+	public void AddFrontmatter_StringsThatLookLikeOtherTypes_AreWrittenQuoted()
+	{
+		string result = Frontmatter.AddFrontmatter("body", new Dictionary<string, object> { ["title"] = "true", ["id"] = "007" });
+		Dictionary<object, object?> header = ReadHeader(result);
+
+		Assert.AreEqual("true", header["title"], result);
+		Assert.AreEqual("007", header["id"], result);
+	}
+
+	[TestMethod]
+	public void ExtractFrontmatter_PlainAndQuotedScalars_KeepDistinctTypes()
+	{
+		Dictionary<string, object>? frontmatter = Frontmatter.ExtractFrontmatter($"---{Nl}draft: false{Nl}label: \"false\"{Nl}---{Nl}body{Nl}");
+
+		Assert.IsNotNull(frontmatter);
+		Assert.IsInstanceOfType<bool>(frontmatter["draft"]);
+		Assert.IsFalse((bool)frontmatter["draft"]);
+		Assert.AreEqual("false", frontmatter["label"]);
+	}
+}
diff --git a/Frontmatter/PropertyMerger.cs b/Frontmatter/PropertyMerger.cs
index baa50d2..121fb4c 100644
--- a/Frontmatter/PropertyMerger.cs
+++ b/Frontmatter/PropertyMerger.cs
@@ -125,6 +125,12 @@ private static void MergePropertyGroup(
 		object firstValue = source[firstKey];
 		if (firstValue == null)
 		{
+			// A null has no type to merge on, so every key keeps its own value rather than being dropped.
+			foreach (string key in originalKeys)
+			{
+				target[key] = source[key];
+			}
+
 			return;
 		}
 
@@ -138,7 +144,7 @@ private static void MergePropertyGroup(
 			// If types are different, keep all properties separate
 			foreach (string key in originalKeys)
 			{
-				target[key] = source[key] ?? throw new InvalidOperationException($"Value for key {key} is null");
+				target[key] = source[key];
 			}
 
 			return;
diff --git a/Frontmatter/YamlSerializer.cs b/Frontmatter/YamlSerializer.cs
index b82ab6e..5552aff 100644
--- a/Frontmatter/YamlSerializer.cs
+++ b/Frontmatter/YamlSerializer.cs
@@ -27,6 +27,7 @@ public static class YamlSerializer
 	private static readonly IDeserializer Deserializer = new DeserializerBuilder()
 		.WithNamingConvention(NullNamingConvention.Instance)
 		.IgnoreUnmatchedProperties()
+		.WithAttemptingUnquotedStringTypeDeserialization()
 		.Build();
 
 	/// <summary>
@@ -35,6 +36,7 @@ public static class YamlSerializer
 	private static readonly ISerializer Serializer = new SerializerBuilder()
 		.WithNamingConvention(NullNamingConvention.Instance)
 		.ConfigureDefaultValuesHandling(DefaultValuesHandling.Preserve)
+		.WithQuotingNecessaryStrings()
 		.Build();
 
 	/// <summary>
@@ -159,7 +161,9 @@ private static object ConvertValue(object? value)
 	{
 		return value switch
 		{
-			null => string.Empty,
+			// A null stays null so it is written back as a null rather than as an empty string. The
+			// dictionaries this feeds are typed as non-nullable for compatibility, so the null is forgiven.
+			null => null!,
 			Dictionary<object, object> dict => dict.ToDictionary(
 				kvp => kvp.Key?.ToString() ?? string.Empty,
 				kvp => ConvertValue(kvp.Value)),