diff --git a/CMakeLists.txt b/CMakeLists.txt
index d68844c0b..fb2be894d 100644
--- a/CMakeLists.txt
+++ b/CMakeLists.txt
@@ -94,6 +94,8 @@ set(REQUIRED_OPENSSL_VERSION 3.0)
 set(REQUIRED_LIBEI_VERSION 1.3)
 set(REQUIRED_LIBPORTAL_VERSION 0.8)
 set(REQUIRED_QT_VERSION 6.7.0)
+set(REQUIRED_MSVC_RUNTIME_MAJOR 14)
+set(REQUIRED_MSVC_RUNTIME_MINOR 42)
 
 # Control debug item visibility
 # When not set logging is forced to DEBUG and show code locations
diff --git a/cspell.json b/cspell.json
index 3d876976f..905ad93f5 100644
--- a/cspell.json
+++ b/cspell.json
@@ -26,6 +26,7 @@
     "Hadzhylov",
     "Hetu",
     "HINSTANCE",
+    "HKLM",
     "hotspots",
     "Hutterer",
     "ifdef",
@@ -65,6 +66,7 @@
     "qobject",
     "qputenv",
     "readf",
+    "Redist",
     "Regen",
     "Repology",
     "Rizzitello",
diff --git a/deploy/windows/deploy.cmake b/deploy/windows/deploy.cmake
index fe71d90cb..1b539dcb2 100644
--- a/deploy/windows/deploy.cmake
+++ b/deploy/windows/deploy.cmake
@@ -53,3 +53,18 @@ configure_file(
 
 # This patch set ups filewall rules, the service and msm module
 set(CPACK_WIX_PATCH_FILE "${CMAKE_CURRENT_BINARY_DIR}/wix-patch.xml")
+
+# Creates a DLL that can be used by our MSI for custom actions.
+configure_file(
+  ${MY_DIR}/wix-custom.h.in
+  ${CMAKE_CURRENT_BINARY_DIR}/wix-custom.h @ONLY
+)
+add_library(
+  wix-custom SHARED
+  ${MY_DIR}/wix-custom.cpp
+)
+target_include_directories(wix-custom PRIVATE ${CMAKE_CURRENT_BINARY_DIR})
+set_target_properties(wix-custom PROPERTIES
+  RUNTIME_OUTPUT_DIRECTORY "${CMAKE_CURRENT_BINARY_DIR}"
+)
+target_link_libraries(wix-custom PRIVATE Msi)
diff --git a/deploy/windows/wix-custom.cpp b/deploy/windows/wix-custom.cpp
new file mode 100644
index 000000000..09a690f34
--- /dev/null
+++ b/deploy/windows/wix-custom.cpp
@@ -0,0 +1,72 @@
+/*
+ * Deskflow -- mouse and keyboard sharing utility
+ * SPDX-FileCopyrightText: (C) 2025 Symless Ltd.
+ * SPDX-License-Identifier: GPL-2.0-only WITH LicenseRef-OpenSSL-Exception
+ */
+
+#include "wix-custom.h"
+
+#define WIN32_LEAN_AND_MEAN
+#include <Windows.h>
+
+// Include after Windows.h
+#include <MsiQuery.h>
+
+#include <stdio.h>
+#include <string>
+
+namespace {
+// Warning: DLL will crash with error code 1603 if we exceed this.
+const auto kLogLineMax = 1024;
+
+// Prefixes log messages with the app name so they're easier to find/filter.
+const std::string kLogPrefix = std::string(kAppId) + " installer: ";
+
+// Note: Resized to log line max when used.
+static std::string s_logMessageBuffer; // NOSONAR - Must be mutable.
+} // namespace
+
+// This log output can be viewed by using the DebugView program.
+#define MS_LOG_DEBUG(message, ...)                                                                                     \
+  s_logMessageBuffer.resize(kLogLineMax);                                                                              \
+  sprintf(s_logMessageBuffer.data(), message, __VA_ARGS__);                                                            \
+  OutputDebugStringA((kLogPrefix + s_logMessageBuffer + "\n").c_str())
+
+extern "C" __declspec(dllexport) UINT __stdcall CheckVCRedist(MSIHANDLE hInstall)
+{
+  const auto kKeyName = TEXT("SOFTWARE\\Microsoft\\VisualStudio\\14.0\\VC\\Runtimes\\x64");
+  const auto kValueName = TEXT("Minor");
+  const auto kProperty = "VC_REDIST_VERSION_OK";
+
+  MS_LOG_DEBUG("checking for msvc redist v%d.%d", kWindowsRuntimeMajor, kWindowsRuntimeMinor);
+
+  HKEY hKey;
+  if (RegOpenKeyEx(HKEY_LOCAL_MACHINE, kKeyName, 0, KEY_READ, &hKey) != ERROR_SUCCESS) {
+    MS_LOG_DEBUG("msvc redist registry key not found");
+    return ERROR_FUNCTION_FAILED;
+  }
+
+  MS_LOG_DEBUG("msvc redist registry key found, querying minor version");
+
+  DWORD minorVersion = 0;
+  DWORD size = sizeof(DWORD);
+  RegQueryValueEx(hKey, kValueName, nullptr, nullptr, (LPBYTE)&minorVersion, &size);
+  RegCloseKey(hKey);
+
+  MS_LOG_DEBUG("msvc redist minor version: %lu", minorVersion);
+
+  if (minorVersion < kWindowsRuntimeMinor) {
+    MS_LOG_DEBUG("msvc redist minor version %lu too low, expected >= %d", minorVersion, kWindowsRuntimeMinor);
+    // Returning success allows the installer will show a friendly error message.
+    return ERROR_SUCCESS;
+  }
+
+  MS_LOG_DEBUG("msvc redist version ok, setting: %s", kProperty);
+  if (MsiSetProperty(hInstall, kProperty, "ok") != ERROR_SUCCESS) {
+    MS_LOG_DEBUG("failed to set property: %s", kProperty);
+    return ERROR_FUNCTION_FAILED;
+  }
+
+  MS_LOG_DEBUG("msvc redist version check successful");
+  return ERROR_SUCCESS;
+}
diff --git a/deploy/windows/wix-custom.h.in b/deploy/windows/wix-custom.h.in
new file mode 100644
index 000000000..23e159d4e
--- /dev/null
+++ b/deploy/windows/wix-custom.h.in
@@ -0,0 +1,14 @@
+/*
+ * Deskflow -- mouse and keyboard sharing utility
+ * SPDX-FileCopyrightText: (C) 2025 Symless Ltd.
+ * SPDX-License-Identifier: GPL-2.0-only WITH LicenseRef-OpenSSL-Exception
+ */
+
+#pragma once
+
+const auto kAppId = "@CMAKE_PROJECT_NAME@";
+
+// clang-format off
+const auto kWindowsRuntimeMajor = @REQUIRED_MSVC_RUNTIME_MAJOR@;
+const auto kWindowsRuntimeMinor = @REQUIRED_MSVC_RUNTIME_MINOR@;
+// clang-format on
diff --git a/deploy/windows/wix-patch.xml.in b/deploy/windows/wix-patch.xml.in
index 55fd1e9b6..b8f53cd94 100644
--- a/deploy/windows/wix-patch.xml.in
+++ b/deploy/windows/wix-patch.xml.in
@@ -32,20 +32,42 @@
       <RegistrySearch
         Id="FindVCRedist"
         Root="HKLM"
-        Key="SOFTWARE\Microsoft\VisualStudio\14.0\VC\Runtimes\x64"
+        Key="SOFTWARE\Microsoft\VisualStudio\@REQUIRED_MSVC_RUNTIME_MAJOR@.0\VC\Runtimes\x64"
         Name="Installed"
         Type="raw" />
     </Property>
 
-    <CustomAction Id="Run_Deskflow" ExeCommand="Deskflow" FileRef="CM_FP_deskflow.exe" Return="asyncNoWait"/>
-    
+    <Binary Id="CustomDLL" SourceFile="@CMAKE_CURRENT_BINARY_DIR@/wix-custom.dll" />
+
+    <CustomAction
+      Id="CheckVCRedist"
+      BinaryRef="CustomDLL"
+      DllEntry="CheckVCRedist"
+      Execute="immediate" />
+
     <CustomAction
       Id="ShowVCRedistError"
-      Error="Latest Microsoft Visual C++ Redistributable is required. Please install it before proceeding."/>
+      Error="Microsoft Visual C++ Redistributable v@REQUIRED_MSVC_RUNTIME_MAJOR@.@REQUIRED_MSVC_RUNTIME_MINOR@ or later is required. Please download and install the latest version and then restart the installation. See our documentation for instructions." />
+
+    <CustomAction
+      Id="RunDeskflow"
+      ExeCommand="Deskflow"
+      FileRef="CM_FP_deskflow.exe"
+      Return="asyncNoWait" />
 
     <InstallExecuteSequence>
-      <Custom Action="ShowVCRedistError" Before="InstallServices" Condition="NOT Installed AND NOT VC_REDIST_INSTALLED"/>
-      <Custom Action="Run_Deskflow" OnExit="success" Condition="NOT Installed"/>
+      <Custom
+        Action="CheckVCRedist"
+        Before="InstallInitialize"
+        Condition="NOT Installed AND VC_REDIST_INSTALLED" />
+      <Custom
+        Action="ShowVCRedistError"
+        Before="InstallInitialize"
+        Condition="NOT Installed AND (NOT VC_REDIST_INSTALLED OR NOT VC_REDIST_VERSION_OK)" />
+      <Custom
+        Action="RunDeskflow"
+        OnExit="success"
+        Condition="NOT Installed" />
     </InstallExecuteSequence>
   </CPackWiXFragment>
 </CPackWiXPatch>
diff --git a/src/lib/arch/win32/ArchMiscWindows.cpp b/src/lib/arch/win32/ArchMiscWindows.cpp
index 9bfabde40..33fd3ff77 100644
--- a/src/lib/arch/win32/ArchMiscWindows.cpp
+++ b/src/lib/arch/win32/ArchMiscWindows.cpp
@@ -20,8 +20,8 @@
 // See table of the compiler versions and the matching runtime DLL versions:
 // https://dev.to/yumetodo/list-of-mscver-and-mscfullver-8nd
 #if _MSC_VER >= 1942 // Visual Studio 2022 Update 12 (v17.12.4)
-const auto kRequiredMajor = 14;
-const auto kRequiredMinor = 42;
+const auto kRequiredMajor = kWindowsRuntimeMajor;
+const auto kRequiredMinor = kWindowsRuntimeMinor;
 #elif _MSC_VER >= 1920 // Visual Studio 2019 Update 7 (v16.7)
 const auto kRequiredMajor = 14;
 const auto kRequiredMinor = 27;
diff --git a/src/lib/common/constants.h.in b/src/lib/common/constants.h.in
index b45543dc0..cf1f30176 100644
--- a/src/lib/common/constants.h.in
+++ b/src/lib/common/constants.h.in
@@ -39,3 +39,12 @@ const auto kTlsCertificateFilename = "@CMAKE_PROJECT_NAME@.pem";
 const auto kTlsFingerprintLocalFilename = "local-fingerprint";
 const auto kTlsFingerprintTrustedServersFilename = "trusted-servers";
 const auto kTlsFingerprintTrustedClientsFilename = "trusted-clients";
+
+#ifdef _WIN32
+
+// clang-format off
+const auto kWindowsRuntimeMajor = @REQUIRED_MSVC_RUNTIME_MAJOR@;
+const auto kWindowsRuntimeMinor = @REQUIRED_MSVC_RUNTIME_MINOR@;
+// clang-format on
+
+#endif