diff --git a/R/manifest.R b/R/manifest.R
index 706d6386..1ac7435c 100644
--- a/R/manifest.R
+++ b/R/manifest.R
@@ -189,15 +189,54 @@
   if (.is_len_0(version_file)) {
     return(paste0("Project: ", projr_version_get()))
   }
+  
+  # Get current and previous project versions
+  current_version <- projr_version_get()
+  previous_version <- NULL
+  
   if (any(grepl("^Project: ", version_file))) {
+    project_line <- grep("^Project: ", version_file, value = TRUE)[[1]]
+    previous_version <- gsub("^Project: ", "", project_line) |> trimws()
     version_file <- version_file[!grepl("^Project: ", version_file)]
   }
-  c(paste0("Project: ", projr_version_get()), version_file)
+  
+  # If project version has changed, mark existing labels with # to indicate
+  # they may be out of date with the new project version
+  if (!is.null(previous_version) && previous_version != current_version) {
+    version_file <- .version_file_mark_labels_stale(version_file)
+  }
+  
+  c(paste0("Project: ", current_version), version_file)
+}
+
+# Mark label versions with # to indicate they may be stale relative to new project version
+.version_file_mark_labels_stale <- function(version_file) {
+  if (.is_len_0(version_file)) {
+    return(version_file)
+  }
+  
+  # Process each line
+  vapply(version_file, function(line) {
+    # Skip if not a label line
+    if (!grepl(": ", line)) {
+      return(line)
+    }
+    
+    # Skip if already marked with # or *
+    if (grepl("#$|\\*$", line)) {
+      return(line)
+    }
+    
+    # Add # to indicate this version may be stale
+    paste0(line, "#")
+  }, character(1), USE.NAMES = FALSE)
 }
 
 .version_file_update_label_version <- function(version_file, # nolint
                                                label,
                                                add_asterisk) {
+  # When updating a label, remove the # marker (if present) since we're now uploading it
+  # The # marker indicates a label that may be stale relative to the current project version
   version_add <- if (add_asterisk) {
     .version_get() |> paste0("*")
   } else {
diff --git a/R/remote-versions.R b/R/remote-versions.R
index 433f1d97..4a6d3fe1 100644
--- a/R/remote-versions.R
+++ b/R/remote-versions.R
@@ -408,7 +408,7 @@
   if (is.null(remote_pre)) {
     return(character(0L))
   }
-  remote_final_vec_basename <- .(
+  remote_final_vec_basename <- .remote_final_ls(
     type, remote_pre_down
   )
   .remote_version_latest_get(remote_final_vec_basename, type, label) |>
@@ -498,10 +498,12 @@
     if (.is_len_0(label_regex)) {
       return(character(0L))
     }
-    # Extract version, removing the asterisk if present
-    version_with_possible_asterisk <- gsub(match_str, "", label_regex) |> trimws()
-    # Remove asterisk for version comparison purposes but don't mark as trusted
-    gsub("\\*$", "", version_with_possible_asterisk) |> .version_v_rm()
+    # Extract version, removing the asterisk and hash if present
+    # * indicates untrusted upload
+    # # indicates potentially stale (not checked against current project version)
+    version_with_markers <- gsub(match_str, "", label_regex) |> trimws()
+    # Remove asterisk and hash for version comparison purposes
+    gsub("\\*$|#$", "", version_with_markers) |> .version_v_rm()
   }
 
 
diff --git a/man/dot-gh_release_create_httr.Rd b/man/dot-gh_release_create_httr.Rd
new file mode 100644
index 00000000..6c334698
--- /dev/null
+++ b/man/dot-gh_release_create_httr.Rd
@@ -0,0 +1,41 @@
+% Generated by roxygen2: do not edit by hand
+% Please edit documentation in R/remote-github-httr.R
+\name{.gh_release_create_httr}
+\alias{.gh_release_create_httr}
+\title{Create a GitHub release using httr}
+\usage{
+.gh_release_create_httr(
+  repo,
+  tag,
+  description,
+  api_url = NULL,
+  token = NULL,
+  draft = FALSE,
+  prerelease = FALSE,
+  target_commitish = NULL
+)
+}
+\arguments{
+\item{repo}{Character string. Repository in format "owner/repo".}
+
+\item{tag}{Character string. Release tag.}
+
+\item{description}{Character string. Release body text.}
+
+\item{api_url}{Character string. Optional GitHub API URL (for Enterprise).}
+
+\item{token}{Character string. Optional GitHub token. If not supplied,
+\code{.auth_get_github_pat_find()} is used.}
+
+\item{draft}{Logical. Whether the release should be created as a draft.}
+
+\item{target_commitish}{Character string. Optional target commitish
+(branch or SHA). If NULL, GitHub uses the default branch.}
+}
+\value{
+Parsed release object (list) from GitHub API on success.
+}
+\description{
+Creates a GitHub release for the given tag using the GitHub REST API.
+}
+\keyword{internal}
diff --git a/man/dot-gh_api_base.Rd b/man/dot-github_api_base.Rd
similarity index 91%
rename from man/dot-gh_api_base.Rd
rename to man/dot-github_api_base.Rd
index 0c50149b..bf2d52bb 100644
--- a/man/dot-gh_api_base.Rd
+++ b/man/dot-github_api_base.Rd
@@ -1,7 +1,7 @@
 % Generated by roxygen2: do not edit by hand
 % Please edit documentation in R/remote-github-httr.R
-\name{.gh_api_base}
-\alias{.gh_api_base}
+\name{.github_api_base}
+\alias{.github_api_base}
 \title{Get GitHub API base URL}
 \usage{
 .github_api_base(api_url = NULL)
diff --git a/man/dot-gh_release_exists_httr.Rd b/man/dot-remote_check_exists_github_httr.Rd
similarity index 70%
rename from man/dot-gh_release_exists_httr.Rd
rename to man/dot-remote_check_exists_github_httr.Rd
index f8352f75..e92cdfd2 100644
--- a/man/dot-gh_release_exists_httr.Rd
+++ b/man/dot-remote_check_exists_github_httr.Rd
@@ -1,10 +1,10 @@
 % Generated by roxygen2: do not edit by hand
 % Please edit documentation in R/remote-github-httr.R
-\name{.gh_release_exists_httr}
-\alias{.gh_release_exists_httr}
+\name{.remote_check_exists_github_httr}
+\alias{.remote_check_exists_github_httr}
 \title{Check if a GitHub release exists using httr}
 \usage{
-.gh_release_exists_httr(repo, tag, api_url = NULL, token = NULL)
+.remote_check_exists_github_httr(repo, tag, api_url = NULL, token = NULL)
 }
 \arguments{
 \item{repo}{Character string. Repository in format "owner/repo".}
@@ -17,11 +17,10 @@
 \code{.auth_get_github_pat_find()}.}
 }
 \value{
-Logical TRUE/FALSE if release exists/doesn't exist, NULL on auth errors.
+Logical TRUE/FALSE if release exists/doesn't exist and stops on auth errors
 }
 \description{
 Uses the GitHub API directly to check if a release with the given tag exists.
 This is faster and more explicit than relying on piggyback internals.
-Returns NULL on authentication errors (401/403) to allow fallback to piggyback.
 }
 \keyword{internal}
diff --git a/man/dot-remote_file_get_all_github_httr.Rd b/man/dot-remote_file_get_all_github_httr.Rd
new file mode 100644
index 00000000..9e73e88a
--- /dev/null
+++ b/man/dot-remote_file_get_all_github_httr.Rd
@@ -0,0 +1,46 @@
+% Generated by roxygen2: do not edit by hand
+% Please edit documentation in R/remote-github-httr.R
+\name{.remote_file_get_all_github_httr}
+\alias{.remote_file_get_all_github_httr}
+\title{Download all assets from a GitHub release using httr}
+\usage{
+.remote_file_get_all_github_httr(
+  repo,
+  tag,
+  fn,
+  dest_dir,
+  api_url = NULL,
+  token = NULL,
+  overwrite = TRUE,
+  output_level = "std",
+  log_file = NULL
+)
+}
+\arguments{
+\item{repo}{Character string. Repository in format "owner/repo".}
+
+\item{tag}{Character string. Release tag.}
+
+\item{dest_dir}{Character string. Local directory to save assets into.
+Created if it does not exist.}
+
+\item{api_url}{Character string. Optional GitHub API URL.}
+
+\item{token}{Character string. Optional GitHub token. If not supplied,
+\code{.auth_get_github_pat_find()} is used.}
+
+\item{overwrite}{Logical. If FALSE, existing files are left untouched.}
+
+\item{output_level}{Character. Verbosity control passed to \code{.cli_debug()}.}
+
+\item{log_file}{Optional log file path for \code{.cli_debug()}.}
+}
+\value{
+Character vector of downloaded file paths (invisibly).
+}
+\description{
+Downloads every asset attached to a GitHub release (identified by tag)
+into a local directory. Uses the GitHub API via \code{httr} and supports
+GitHub Enterprise via \code{api_url}.
+}
+\keyword{internal}
diff --git a/man/dot-gh_release_asset_delete_httr.Rd b/man/dot-remote_final_empty_github_httr.Rd
similarity index 76%
rename from man/dot-gh_release_asset_delete_httr.Rd
rename to man/dot-remote_final_empty_github_httr.Rd
index 82db45cf..fd6fa52d 100644
--- a/man/dot-gh_release_asset_delete_httr.Rd
+++ b/man/dot-remote_final_empty_github_httr.Rd
@@ -1,19 +1,19 @@
 % Generated by roxygen2: do not edit by hand
 % Please edit documentation in R/remote-github-httr.R
-\name{.gh_release_asset_delete_httr}
-\alias{.gh_release_asset_delete_httr}
+\name{.remote_final_empty_github_httr}
+\alias{.remote_final_empty_github_httr}
 \title{Delete a release asset using httr}
 \usage{
-.gh_release_asset_delete_httr(repo, asset_id, api_url = NULL, token = NULL)
+.remote_final_empty_github_httr(repo, tag, fn, api_url = NULL, token = NULL)
 }
 \arguments{
 \item{repo}{Character string. Repository in format "owner/repo".}
 
-\item{asset_id}{Numeric. Asset ID to delete.}
-
 \item{api_url}{Character string. Optional GitHub API URL.}
 
 \item{token}{Character string. Optional GitHub token.}
+
+\item{asset_id}{Numeric. Asset ID to delete.}
 }
 \value{
 Logical. TRUE if successful.
diff --git a/man/dot-gh_release_get_httr.Rd b/man/dot-remote_ls_final_github_httr.Rd
similarity index 79%
rename from man/dot-gh_release_get_httr.Rd
rename to man/dot-remote_ls_final_github_httr.Rd
index 43245b45..be31dc81 100644
--- a/man/dot-gh_release_get_httr.Rd
+++ b/man/dot-remote_ls_final_github_httr.Rd
@@ -1,10 +1,10 @@
 % Generated by roxygen2: do not edit by hand
 % Please edit documentation in R/remote-github-httr.R
-\name{.gh_release_get_httr}
-\alias{.gh_release_get_httr}
+\name{.remote_ls_final_github_httr}
+\alias{.remote_ls_final_github_httr}
 \title{Get release information by tag using httr}
 \usage{
-.gh_release_get_httr(repo, tag, api_url = NULL, token = NULL)
+.remote_ls_final_github_httr(repo, tag, api_url = NULL, token = NULL)
 }
 \arguments{
 \item{repo}{Character string. Repository in format "owner/repo".}
diff --git a/man/projr_osf_create_project.Rd b/man/projr_osf_create_project.Rd
index cf9a9402..ca5c18b4 100644
--- a/man/projr_osf_create_project.Rd
+++ b/man/projr_osf_create_project.Rd
@@ -1,5 +1,5 @@
 % Generated by roxygen2: do not edit by hand
-% Please edit documentation in R/remote.R
+% Please edit documentation in R/remote-osf.R
 \name{projr_osf_create_project}
 \alias{projr_osf_create_project}
 \title{Create a new project on OSF}
diff --git a/tests/testthat/test-version-file-hash-marker.R b/tests/testthat/test-version-file-hash-marker.R
new file mode 100644
index 00000000..d164167d
--- /dev/null
+++ b/tests/testthat/test-version-file-hash-marker.R
@@ -0,0 +1,142 @@
+test_that(".version_file_mark_labels_stale marks labels with hash", {
+  skip_if(.is_test_select())
+  
+  # Test with no labels
+  version_file <- character(0L)
+  result <- .version_file_mark_labels_stale(version_file)
+  expect_identical(result, character(0L))
+  
+  # Test with one label
+  version_file <- c("raw-data: v0.3.0")
+  result <- .version_file_mark_labels_stale(version_file)
+  expect_identical(result, c("raw-data: v0.3.0#"))
+  
+  # Test with multiple labels
+  version_file <- c("raw-data: v0.3.0", "cache: v0.2.0")
+  result <- .version_file_mark_labels_stale(version_file)
+  expect_identical(result, c("raw-data: v0.3.0#", "cache: v0.2.0#"))
+  
+  # Test with label already having asterisk (don't add hash)
+  version_file <- c("raw-data: v0.3.0*")
+  result <- .version_file_mark_labels_stale(version_file)
+  expect_identical(result, c("raw-data: v0.3.0*"))
+  
+  # Test with label already having hash (don't add another)
+  version_file <- c("raw-data: v0.3.0#")
+  result <- .version_file_mark_labels_stale(version_file)
+  expect_identical(result, c("raw-data: v0.3.0#"))
+  
+  # Test with mixed markers
+  version_file <- c("raw-data: v0.3.0", "cache: v0.2.0*", "output: v0.1.0#")
+  result <- .version_file_mark_labels_stale(version_file)
+  expect_identical(result, c("raw-data: v0.3.0#", "cache: v0.2.0*", "output: v0.1.0#"))
+})
+
+test_that(".version_file_update_project_version marks labels stale when version changes", {
+  skip_if(.is_test_select())
+  dir_test <- .test_setup_project(git = FALSE, set_env_var = TRUE)
+  usethis::with_project(
+    path = dir_test,
+    code = {
+      # Start with empty version file
+      version_file <- character(0L)
+      result <- .version_file_update_project_version(version_file)
+      expect_identical(result[[1]], paste0("Project: ", projr_version_get()))
+      expect_identical(length(result), 1L)
+      
+      # Add a label version, then update project version (no change)
+      projr_version_set("0.0.1")
+      version_file <- c("Project: 0.0.1", "raw-data: v0.0.1")
+      
+      result <- .version_file_update_project_version(version_file)
+      # Should not add hash since version didn't change
+      expect_identical(result, c("Project: 0.0.1", "raw-data: v0.0.1"))
+      
+      # Now bump project version and update
+      projr_version_set("0.0.2")
+      result <- .version_file_update_project_version(version_file)
+      # Should add hash to raw-data since project version changed
+      expect_identical(result[[1]], "Project: 0.0.2")
+      expect_identical(result[[2]], "raw-data: v0.0.1#")
+      
+      # Multiple labels with version change
+      projr_version_set("0.0.3")
+      version_file <- c("Project: 0.0.2", "raw-data: v0.0.2", "cache: v0.0.1")
+      result <- .version_file_update_project_version(version_file)
+      expect_identical(result[[1]], "Project: 0.0.3")
+      expect_identical(result[[2]], "raw-data: v0.0.2#")
+      expect_identical(result[[3]], "cache: v0.0.1#")
+      
+      # Label with asterisk should keep it when adding hash (but only add hash, not replace)
+      projr_version_set("0.0.4")
+      version_file <- c("Project: 0.0.3", "raw-data: v0.0.3*")
+      result <- .version_file_update_project_version(version_file)
+      expect_identical(result[[1]], "Project: 0.0.4")
+      expect_identical(result[[2]], "raw-data: v0.0.3*")
+    }
+  )
+})
+
+test_that(".version_file_update_label_version removes hash marker", {
+  skip_if(.is_test_select())
+  dir_test <- .test_setup_project(git = FALSE, set_env_var = TRUE)
+  usethis::with_project(
+    path = dir_test,
+    code = {
+      projr_version_set("0.0.5")
+      
+      # Add new label (no hash to remove)
+      version_file <- c("Project: 0.0.5")
+      result <- .version_file_update_label_version(version_file, "raw-data", FALSE)
+      expect_identical(result[[2]], "raw-data: 0.0.5")
+      
+      # Update existing label with hash (should remove hash)
+      version_file <- c("Project: 0.0.5", "raw-data: v0.0.3#")
+      result <- .version_file_update_label_version(version_file, "raw-data", FALSE)
+      expect_identical(result[[2]], "raw-data: 0.0.5")
+      expect_false(grepl("#", result[[2]]))
+      
+      # Update with asterisk should not have hash
+      version_file <- c("Project: 0.0.5", "raw-data: v0.0.3#")
+      result <- .version_file_update_label_version(version_file, "raw-data", TRUE)
+      expect_identical(result[[2]], "raw-data: 0.0.5*")
+      expect_false(grepl("#", result[[2]]))
+    }
+  )
+})
+
+test_that(".remote_get_version_label_non_project_file_extract handles hash marker", {
+  skip_if(.is_test_select())
+  
+  # Test extracting version without markers
+  version_file <- c("Project: v0.5.0", "raw-data: v0.3.0")
+  result <- .remote_get_version_label_non_project_file_extract(version_file, "raw-data")
+  expect_identical(result, "0.3.0")
+  
+  # Test extracting version with hash marker
+  version_file <- c("Project: v0.5.0", "raw-data: v0.3.0#")
+  result <- .remote_get_version_label_non_project_file_extract(version_file, "raw-data")
+  expect_identical(result, "0.3.0")
+  
+  # Test extracting version with asterisk marker
+  version_file <- c("Project: v0.5.0", "raw-data: v0.3.0*")
+  result <- .remote_get_version_label_non_project_file_extract(version_file, "raw-data")
+  expect_identical(result, "0.3.0")
+  
+  # Test extracting version with both markers should not happen in practice
+  # but should still extract version correctly
+  version_file <- c("Project: v0.5.0", "raw-data: v0.3.0#")
+  result <- .remote_get_version_label_non_project_file_extract(version_file, "raw-data")
+  expect_identical(result, "0.3.0")
+  
+  # Test with multiple labels, extract specific one
+  version_file <- c("Project: v0.5.0", "raw-data: v0.3.0#", "cache: v0.2.0", "output: v0.4.0*")
+  result <- .remote_get_version_label_non_project_file_extract(version_file, "cache")
+  expect_identical(result, "0.2.0")
+  
+  result <- .remote_get_version_label_non_project_file_extract(version_file, "raw-data")
+  expect_identical(result, "0.3.0")
+  
+  result <- .remote_get_version_label_non_project_file_extract(version_file, "output")
+  expect_identical(result, "0.4.0")
+})