diff --git a/CHANGELOG.md b/CHANGELOG.md
index 9ff1797ff..9779b3ed2 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -8,6 +8,10 @@ The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/).
 - Include more cuda (nvidia) filters in docker image
 - Enable deinterlacing with nvidia using new `yadif_cuda` filter
 
+### Changed
+- Upgrade ffmpeg from 4.3 to 4.4 in all docker images
+  - Upgrading from 4.3 to 4.4 is recommended for all installations
+
 ### Fixed
 - Fix some transcoding edge cases with nvidia and pixel format `yuv420p10le`
 
diff --git a/ErsatzTV.Infrastructure/Health/Checks/FFmpegVersionHealthCheck.cs b/ErsatzTV.Infrastructure/Health/Checks/FFmpegVersionHealthCheck.cs
index b9a11f2c9..074c71913 100644
--- a/ErsatzTV.Infrastructure/Health/Checks/FFmpegVersionHealthCheck.cs
+++ b/ErsatzTV.Infrastructure/Health/Checks/FFmpegVersionHealthCheck.cs
@@ -11,6 +11,7 @@ namespace ErsatzTV.Infrastructure.Health.Checks
 {
     public class FFmpegVersionHealthCheck : BaseHealthCheck, IFFmpegVersionHealthCheck
     {
+        private const string BundledVersion = "N-104321-ga742ba60f1";
         private readonly IConfigElementRepository _configElementRepository;
 
         public FFmpegVersionHealthCheck(IConfigElementRepository configElementRepository)
@@ -72,17 +73,17 @@ namespace ErsatzTV.Infrastructure.Health.Checks
         {
             if (version.StartsWith("3."))
             {
-                return FailResult($"{app} version {version} is too old; please install 4.3!");
+                return FailResult($"{app} version {version} is too old; please install 4.4!");
             }
 
-            if (version.StartsWith("4.4"))
+            if (version.StartsWith("4.3"))
             {
-                return FailResult($"{app} version 4.4 is known to have issues; please install 4.3!");
+                return WarningResult($"{app} version 4.4 is now supported, please upgrade from 4.3!");
             }
 
-            if (!version.StartsWith("4.3"))
+            if (!version.StartsWith("4.4") && version != BundledVersion)
             {
-                return WarningResult($"{app} version {version} is unexpected and may have problems; please install 4.3!");
+                return WarningResult($"{app} version {version} is unexpected and may have problems; please install 4.4!");
             }
 
             return None;
diff --git a/docker/Dockerfile b/docker/Dockerfile
index 38db66278..fe613dc69 100644
--- a/docker/Dockerfile
+++ b/docker/Dockerfile
@@ -1,6 +1,6 @@
 FROM mcr.microsoft.com/dotnet/aspnet:5.0-focal-amd64 AS dotnet-runtime
 
-FROM jrottenberg/ffmpeg:4.3-ubuntu2004 AS runtime-base
+FROM jasongdove/ffmpeg:4.4-ubuntu2004 AS runtime-base
 COPY --from=dotnet-runtime /usr/share/dotnet /usr/share/dotnet
 RUN apt-get update && DEBIAN_FRONTEND="noninteractive" apt-get install -y libicu-dev tzdata
 
diff --git a/docker/nvidia/Dockerfile b/docker/nvidia/Dockerfile
index b0fb67e47..234919957 100644
--- a/docker/nvidia/Dockerfile
+++ b/docker/nvidia/Dockerfile
@@ -23,7 +23,7 @@ ARG INFO_VERSION="unknown"
 RUN dotnet publish -c release -o /app -r linux-x64 --self-contained false --no-restore /p:InformationalVersion=${INFO_VERSION}
 
 # final stage/image
-FROM jasongdove/ffmpeg:4.3-nvidia2004 AS runtime-base
+FROM jasongdove/ffmpeg:4.4-nvidia2004 AS runtime-base
 WORKDIR /app
 EXPOSE 8409
 COPY --from=build /app ./
diff --git a/docker/nvidia/ffmpeg.Dockerfile b/docker/nvidia/ffmpeg.Dockerfile
index cfc130340..b7396b043 100644
--- a/docker/nvidia/ffmpeg.Dockerfile
+++ b/docker/nvidia/ffmpeg.Dockerfile
@@ -1,6 +1,6 @@
 FROM mcr.microsoft.com/dotnet/aspnet:5.0-focal-amd64 AS dotnet-runtime
 
-FROM jasongdove/ffmpeg-base:4.3-nvidia2004 AS runtime-base
+FROM jasongdove/ffmpeg-base:4.4-nvidia2004 AS runtime-base
 COPY --from=dotnet-runtime /usr/share/dotnet /usr/share/dotnet
 RUN apt-get update \
     && DEBIAN_FRONTEND="noninteractive" apt-get install -y libicu-dev tzdata \
diff --git a/docker/vaapi/ffmpeg.Dockerfile b/docker/vaapi/ffmpeg.Dockerfile
index 9e53755df..acce362c9 100644
--- a/docker/vaapi/ffmpeg.Dockerfile
+++ b/docker/vaapi/ffmpeg.Dockerfile
@@ -1,6 +1,6 @@
 FROM mcr.microsoft.com/dotnet/aspnet:5.0-focal-amd64 AS dotnet-runtime
 
-FROM jrottenberg/ffmpeg:4.3-vaapi2004 AS runtime-base
+FROM jasongdove/ffmpeg-base:4.4-vaapi2004 AS runtime-base
 COPY --from=dotnet-runtime /usr/share/dotnet /usr/share/dotnet
 RUN apt-get update && DEBIAN_FRONTEND="noninteractive" apt-get install -y libicu-dev \
     tzdata \