Solution to reproduce the bug including the PDF

App.config

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+<?xml version="1.0" encoding="utf-8" ?>
+<configuration>
+    <startup> 
+        <supportedRuntime version="v4.0" sku=".NETFramework,Version=v4.7.2" />
+    </startup>
+</configuration>

IronPdf_turn180degree_FormatBug.csproj

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+<?xml version="1.0" encoding="utf-8"?>
+<Project ToolsVersion="15.0" xmlns="http://schemas.microsoft.com/developer/msbuild/2003">
+  <Import Project="$(MSBuildExtensionsPath)\$(MSBuildToolsVersion)\Microsoft.Common.props" Condition="Exists('$(MSBuildExtensionsPath)\$(MSBuildToolsVersion)\Microsoft.Common.props')" />
+  <PropertyGroup>
+    <Configuration Condition=" '$(Configuration)' == '' ">Debug</Configuration>
+    <Platform Condition=" '$(Platform)' == '' ">AnyCPU</Platform>
+    <ProjectGuid>{53D8BFC3-4D33-4C51-BA1C-DA92D05177A4}</ProjectGuid>
+    <OutputType>Exe</OutputType>
+    <RootNamespace>IronPdf_turn180degree_FormatBug</RootNamespace>
+    <AssemblyName>IronPdf_turn180degree_FormatBug</AssemblyName>
+    <TargetFrameworkVersion>v4.7.2</TargetFrameworkVersion>
+    <FileAlignment>512</FileAlignment>
+    <AutoGenerateBindingRedirects>true</AutoGenerateBindingRedirects>
+    <Deterministic>true</Deterministic>
+  </PropertyGroup>
+  <PropertyGroup Condition=" '$(Configuration)|$(Platform)' == 'Debug|AnyCPU' ">
+    <PlatformTarget>AnyCPU</PlatformTarget>
+    <DebugSymbols>true</DebugSymbols>
+    <DebugType>full</DebugType>
+    <Optimize>false</Optimize>
+    <OutputPath>bin\Debug\</OutputPath>
+    <DefineConstants>DEBUG;TRACE</DefineConstants>
+    <ErrorReport>prompt</ErrorReport>
+    <WarningLevel>4</WarningLevel>
+  </PropertyGroup>
+  <PropertyGroup Condition=" '$(Configuration)|$(Platform)' == 'Release|AnyCPU' ">
+    <PlatformTarget>AnyCPU</PlatformTarget>
+    <DebugType>pdbonly</DebugType>
+    <Optimize>true</Optimize>
+    <OutputPath>bin\Release\</OutputPath>
+    <DefineConstants>TRACE</DefineConstants>
+    <ErrorReport>prompt</ErrorReport>
+    <WarningLevel>4</WarningLevel>
+  </PropertyGroup>
+  <ItemGroup>
+    <Reference Include="IronPdf, Version=5.2.0.22321, Culture=neutral, processorArchitecture=MSIL">
+      <HintPath>packages\IronPdf.5.2.0.1\lib\net40\IronPdf.dll</HintPath>
+    </Reference>
+    <Reference Include="System" />
+    <Reference Include="System.Core" />
+    <Reference Include="System.Drawing" />
+    <Reference Include="System.Web" />
+    <Reference Include="System.Xml.Linq" />
+    <Reference Include="System.Data.DataSetExtensions" />
+    <Reference Include="Microsoft.CSharp" />
+    <Reference Include="System.Data" />
+    <Reference Include="System.Net.Http" />
+    <Reference Include="System.Xml" />
+  </ItemGroup>
+  <ItemGroup>
+    <Compile Include="Program.cs" />
+    <Compile Include="Properties\AssemblyInfo.cs" />
+  </ItemGroup>
+  <ItemGroup>
+    <None Include="App.config" />
+    <None Include="packages.config" />
+    <None Include="test_formula.pdf">
+      <CopyToOutputDirectory>PreserveNewest</CopyToOutputDirectory>
+    </None>
+  </ItemGroup>
+  <Import Project="$(MSBuildToolsPath)\Microsoft.CSharp.targets" />
+</Project>

IronPdf_turn180degree_FormatBug.csproj.user

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+<?xml version="1.0" encoding="utf-8"?>
+<Project ToolsVersion="15.0" xmlns="http://schemas.microsoft.com/developer/msbuild/2003">
+  <PropertyGroup>
+    <ProjectView>ShowAllFiles</ProjectView>
+  </PropertyGroup>
+</Project>

IronPdf_turn180degree_FormatBug.sln

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+
+Microsoft Visual Studio Solution File, Format Version 12.00
+# Visual Studio 15
+VisualStudioVersion = 15.0.28307.572
+MinimumVisualStudioVersion = 10.0.40219.1
+Project("{FAE04EC0-301F-11D3-BF4B-00C04F79EFBC}") = "IronPdf_turn180degree_FormatBug", "IronPdf_turn180degree_FormatBug.csproj", "{53D8BFC3-4D33-4C51-BA1C-DA92D05177A4}"
+EndProject
+Global
+	GlobalSection(SolutionConfigurationPlatforms) = preSolution
+		Debug|Any CPU = Debug|Any CPU
+		Release|Any CPU = Release|Any CPU
+	EndGlobalSection
+	GlobalSection(ProjectConfigurationPlatforms) = postSolution
+		{53D8BFC3-4D33-4C51-BA1C-DA92D05177A4}.Debug|Any CPU.ActiveCfg = Debug|Any CPU
+		{53D8BFC3-4D33-4C51-BA1C-DA92D05177A4}.Debug|Any CPU.Build.0 = Debug|Any CPU
+		{53D8BFC3-4D33-4C51-BA1C-DA92D05177A4}.Release|Any CPU.ActiveCfg = Release|Any CPU
+		{53D8BFC3-4D33-4C51-BA1C-DA92D05177A4}.Release|Any CPU.Build.0 = Release|Any CPU
+	EndGlobalSection
+	GlobalSection(SolutionProperties) = preSolution
+		HideSolutionNode = FALSE
+	EndGlobalSection
+	GlobalSection(ExtensibilityGlobals) = postSolution
+		SolutionGuid = {B7AB5CB2-8045-4A33-8C1E-63333E2BFA5A}
+	EndGlobalSection
+EndGlobal

Program.cs

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+using System.IO;
+using System.Reflection;
+using IronPdf;
+
+namespace IronPdf_turn180degree_FormatBug
+{
+    internal class Program
+    {
+        private static void Main()
+        {
+            var filenamePattern = new FileInfo(Assembly.GetExecutingAssembly().Location).Directory +
+                                  @"\test_formula#rotation#.pdf";
+            var rotated000 = filenamePattern.Replace("#rotation#", string.Empty);
+            var rotated090 = filenamePattern.Replace("#rotation#", "_090");
+            var rotated180 = filenamePattern.Replace("#rotation#", "_180");
+            var rotated270 = filenamePattern.Replace("#rotation#", "_270");
+            var rotated360 = filenamePattern.Replace("#rotation#", "_360");
+
+            var pdf = new PdfDocument(rotated000);
+            pdf.RotateAllPages(90); //90
+            while (!pdf.Stream.CanWrite) continue;
+
+            pdf.SaveAs(rotated090); //incorrect
+            pdf.RotateAllPages(90); //180
+            while (!pdf.Stream.CanWrite) continue;
+
+            pdf.SaveAs(rotated180); //correct
+
+
+            pdf.RotateAllPages(90); //270
+            while (!pdf.Stream.CanWrite) continue;
+
+            pdf.SaveAs(rotated270); //incorrect
+
+
+            pdf.RotateAllPages(90); //360
+            while (!pdf.Stream.CanWrite) continue;
+
+            pdf.SaveAs(rotated360); //correct
+        }
+    }
+}

packages.config

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+<?xml version="1.0" encoding="utf-8"?>
+<packages>
+  <package id="IronPdf" version="5.2.0.1" targetFramework="net472" />
+</packages>