diff --git a/Justfile b/Justfile
index 39086128..e29554d0 100644
--- a/Justfile
+++ b/Justfile
@@ -8,7 +8,7 @@ sed_vars := if os() == "macos" { "-i ''" } else { "-i" }
 BUILDX_PATH := ""
 
 RSC_VERSION := "2024.05.0"
-RSPM_VERSION := "2024.04.0-20"
+RSPM_VERSION := "2024.04.2-29"
 RSW_VERSION := "2024.04.1+748.pro2"
 
 DRIVERS_VERSION := "2023.05.0"
diff --git a/docker-bake.hcl b/docker-bake.hcl
index 5dcdeb03..64aeb20c 100644
--- a/docker-bake.hcl
+++ b/docker-bake.hcl
@@ -4,7 +4,7 @@ variable CONNECT_VERSION {
 }
 
 variable PACKAGE_MANAGER_VERSION {
-    default = "2024.04.0-20"
+    default = "2024.04.2-29"
 }
 
 variable WORKBENCH_VERSION {
@@ -110,7 +110,7 @@ variable PRO_BUILD_MATRIX {
 variable PACKAGE_MANAGER_BUILD_MATRIX {
     default = {
         builds = [
-            {os = "ubuntu2204", r_primary = "4.2.3", r_alternate = "4.1.3", py_primary = "3.12.1", py_alternate = "3.11.7"},
+            {os = "ubuntu2204", r_primary = "4.4.0", r_alternate = "4.3.3", py_primary = "3.12.1", py_alternate = "3.11.7"},
         ]
     }
 }
diff --git a/package-manager/.env b/package-manager/.env
index f24c5043..7c279d2e 100644
--- a/package-manager/.env
+++ b/package-manager/.env
@@ -1,5 +1,5 @@
-RSPM_VERSION=2024.04.0-20
-R_VERSION=4.2.3
+RSPM_VERSION=2024.04.2-29
+R_VERSION=4.4.0
 R_VERSION_ALT=4.1.3
 PYTHON_VERSION=3.9.17
 PYTHON_VERSION_ALT=3.8.17
diff --git a/package-manager/Dockerfile.ubuntu2204 b/package-manager/Dockerfile.ubuntu2204
index fbe02447..7d6d6316 100644
--- a/package-manager/Dockerfile.ubuntu2204
+++ b/package-manager/Dockerfile.ubuntu2204
@@ -13,7 +13,7 @@ RUN /opt/python/${PYTHON_VERSION}/bin/python3 -m pip install --no-cache-dir buil
 RUN /opt/python/${PYTHON_VERSION_ALT}/bin/python3 -m pip install --no-cache-dir build virtualenv
 
 # Download RStudio Package Manager ---------------------------------------------#
-ARG RSPM_VERSION=2024.04.0-20
+ARG RSPM_VERSION=2024.04.2-29
 ARG RSPM_DOWNLOAD_URL=https://cdn.rstudio.com/package-manager/deb/amd64
 RUN curl -O ${RSPM_DOWNLOAD_URL}/rstudio-pm_${RSPM_VERSION}_amd64.deb \
     # Pre 7/25/23 packages
diff --git a/package-manager/NEWS.md b/package-manager/NEWS.md
index 353efa22..a59cf4ff 100644
--- a/package-manager/NEWS.md
+++ b/package-manager/NEWS.md
@@ -1,3 +1,6 @@
+# 2024-05-31
+- Update R to 4.4.0
+
 # 2024-01-11
 - Update Python to 3.12.1
 
diff --git a/package-manager/README.md b/package-manager/README.md
index 824a9dd2..aade5bec 100644
--- a/package-manager/README.md
+++ b/package-manager/README.md
@@ -6,16 +6,16 @@
 
 # Supported tags and respective Dockerfile links
 
-* [`jammy`, `ubuntu2204`, `jammy-2023.12.0`, `ubuntu2204-2023.12.0`](https://github.com/rstudio/rstudio-docker-products/blob/main/package-manager/Dockerfile.ubuntu2204)
+* [`jammy`, `ubuntu2204`, `jammy-2024.04.2`, `ubuntu2204-2024.04.2`](https://github.com/rstudio/rstudio-docker-products/blob/main/package-manager/Dockerfile.ubuntu2204)
 
 # What is RStudio Package Manager?
 
-Posit Package Manager, formerly RStudio Package Manager, is a repository management server to organize and centralize 
-R packages across your team, department, or entire organization. Get offline access to CRAN, automate CRAN syncs, 
-share local packages, restrict package access, find packages across repositories, and more. Experience reliable and 
+Posit Package Manager, formerly RStudio Package Manager, is a repository management server to organize and centralize
+R packages across your team, department, or entire organization. Get offline access to CRAN, automate CRAN syncs,
+share local packages, restrict package access, find packages across repositories, and more. Experience reliable and
 consistent package management, optimized for teams who use R.
 
-The following documentation helps an administrator install and configure Package Manager. It provides information for 
+The following documentation helps an administrator install and configure Package Manager. It provides information for
 installing the product on different operating systems, upgrading, and configuring Package Manager.
 
 # Notice for support
@@ -148,15 +148,15 @@ to [create and manage](https://docs.rstudio.com/rspm/admin/getting-started/confi
 *Note: This section **does not** apply to activations using license files.*
 
 There is currently a known licensing bug when using our products in containers. If the container is not stopped
-gracefully, the license deactivation step may fail or be skipped. Failing to deactivate the license can result in a 
-"license leak" where a product activation is used up and cannot be deactivated using traditional methods as the 
+gracefully, the license deactivation step may fail or be skipped. Failing to deactivate the license can result in a
+"license leak" where a product activation is used up and cannot be deactivated using traditional methods as the
 activation state on the container has been lost.
 
-To avoid "leaking" licenses, we encourage users not to force kill containers and to use `--stop-timeout 120` and 
-`--time 120` for `docker run` and `docker stop` commands respectively. This helps ensure the deactivation script has 
+To avoid "leaking" licenses, we encourage users not to force kill containers and to use `--stop-timeout 120` and
+`--time 120` for `docker run` and `docker stop` commands respectively. This helps ensure the deactivation script has
 ample time to run properly.
 
-In some situations, it can be difficult or impossible to avoid a hard termination (e.g. power failure, 
+In some situations, it can be difficult or impossible to avoid a hard termination (e.g. power failure,
 critical error on host). Unfortunately, any of these cases can still cause a license to leak an activation. To help
 prevent a license leak in these situations, users can mount the following directories to persistent storage to preserve
 the license state data across restarts of the container. **These directories differ between products.**
@@ -171,13 +171,13 @@ the license state data across restarts of the container. **These directories dif
 Please note that the files created in these directories are hardware locked and non-transferable between hosts. Due to
 the nature of the hardware fingerprinting algorithm, any low-level changes to the host or container can cause existing
 license state files to invalidate. To avoid this problem, we advise that product containers are gracefully shutdown
-and allowed to deactivate prior to changing any hardware or firmware on the host (e.g. upgrading a network card or 
+and allowed to deactivate prior to changing any hardware or firmware on the host (e.g. upgrading a network card or
 updating BIOS) or the container (e.g. changing the network driver used or the allocated number of CPU cores).
 
 While preserving license state data *can* help avoid license leaks across restarts, it's not a guarantee. If you run
 into issues with your license, please do not hesitate to [contact Posit support](https://support.posit.co/hc/en-us).
 
-While neither of these solutions will eliminate the problem, they should help mitigate it. We are still investigating a 
+While neither of these solutions will eliminate the problem, they should help mitigate it. We are still investigating a
 long-term solution.
 
 # Licensing