diff --git a/lua/rocks/health.lua b/lua/rocks/health.lua
index a69436e8..1395357b 100644
--- a/lua/rocks/health.lua
+++ b/lua/rocks/health.lua
@@ -119,7 +119,7 @@ local function check_external_dependency(dep)
 end
 
 local function check_config()
-    start("Checking config")
+    start("Checking rocks.nvim config")
     if vim.g.rocks_nvim and not config.debug_info.was_g_rocks_nvim_sourced then
         warn("unrecognized configs in vim.g.rocks_nvim: " .. vim.inspect(config.debug_info.unrecognized_configs))
     end
@@ -131,12 +131,29 @@ local function check_config()
     end
 end
 
+local function check_rocks_toml()
+    start("Checking rocks.toml")
+    local success, user_rocks_or_err = xpcall(require("rocks.config.internal").get_user_rocks, function(err)
+        error(err)
+    end)
+    if not success then
+        return
+    end
+    for rock_name, _ in pairs(user_rocks_or_err) do
+        if rock_name:lower() ~= rock_name then
+            error(("Plugin name is not lowercase: %s"):format(rock_name))
+        end
+        ok("No errors found in rocks.toml.")
+    end
+end
+
 function health.check()
     start("Checking external dependencies")
     for _, dep in ipairs(external_dependencies) do
         check_external_dependency(dep)
     end
     check_config()
+    check_rocks_toml()
 end
 
 return health
diff --git a/lua/rocks/operations/init.lua b/lua/rocks/operations/init.lua
index b6688096..52ed4836 100644
--- a/lua/rocks/operations/init.lua
+++ b/lua/rocks/operations/init.lua
@@ -113,7 +113,8 @@ operations.sync = function(user_rocks, on_complete)
         end
         if user_rocks == nil then
             -- Read or create a new config file and decode it
-            -- NOTE: This does not use parse_user_rocks because we decode with toml, not toml-edit
+            -- NOTE: This does not use parse_user_rocks
+            -- because we decode with toml-edit.parse_as_tbl, not toml-edit.parse
             user_rocks = config.get_user_rocks()
         end
 
@@ -174,16 +175,29 @@ operations.sync = function(user_rocks, on_complete)
             return get_percentage(ct, action_count)
         end
 
-        ---@type RockSpec[]
+        ---@class SyncSkippedRock
+        ---@field spec RockSpec
+        ---@field reason string
+
+        ---@type SyncSkippedRock[]
         local skipped_rocks = {}
 
         for _, key in ipairs(to_install) do
-            nio.scheduler()
+            -- Save skipped rocks for later, when an external handler may have been bootstrapped
             if not user_rocks[key].version then
-                -- Save it for later, when an external handler may have been bootstrapped
-                table.insert(skipped_rocks, user_rocks[key])
+                table.insert(skipped_rocks, {
+                    spec = user_rocks[key],
+                    reason = "No version specified",
+                })
+                goto skip_install
+            elseif key:lower() ~= key then
+                table.insert(skipped_rocks, {
+                    spec = user_rocks[key],
+                    reason = "Name is not lowercase",
+                })
                 goto skip_install
             end
+            nio.scheduler()
             progress_handle:report({
                 message = ("Installing: %s"):format(key),
             })
@@ -218,13 +232,14 @@ operations.sync = function(user_rocks, on_complete)
 
         -- rocks.nvim sync handlers should be installed now.
         -- try installing any rocks that rocks.nvim could not handle itself
-        for _, spec in ipairs(skipped_rocks) do
+        for _, skipped_rock in ipairs(skipped_rocks) do
+            local spec = skipped_rock.spec
             ct = ct + 1
             local callback = handlers.get_sync_handler_callback(spec)
             if callback then
                 callback(report_progress, report_error)
             else
-                report_error(("Failed to install %s."):format(spec.name))
+                report_error(("Failed to install %s: %s"):format(spec.name, skipped_rock.reason))
             end
         end
 
@@ -529,7 +544,7 @@ operations.add = function(arg_list, callback)
             return
         end
         ---@type rock_name
-        local rock_name = arg_list[1]
+        local rock_name = arg_list[1]:lower()
         -- We can't mutate the arg_list, because we may need it for a recursive add
         ---@type string[]
         local args = #arg_list == 1 and {} or { unpack(arg_list, 2, #arg_list) }
diff --git a/spec/operations/install_update_spec.lua b/spec/operations/install_update_spec.lua
index 19e95b00..7b0a28e7 100644
--- a/spec/operations/install_update_spec.lua
+++ b/spec/operations/install_update_spec.lua
@@ -12,7 +12,7 @@ describe("install/update", function()
     local state = require("rocks.state")
     nio.tests.it("install and update rocks", function()
         local future = nio.control.future()
-        operations.add({ "neorg", "7.0.0" }, function()
+        operations.add({ "Neorg", "7.0.0" }, function() -- ensure lower case
             future.set(true)
         end)
         future.wait()
@@ -21,6 +21,12 @@ describe("install/update", function()
             name = "neorg",
             version = "7.0.0",
         }, installed_rocks.neorg)
+        nio.sleep(1000) -- Time to write to rocks.toml
+        local user_rocks = require("rocks.config.internal").get_user_rocks()
+        assert.same({
+            name = "neorg",
+            version = "7.0.0",
+        }, user_rocks.neorg)
         future = nio.control.future()
         operations.update(function()
             future.set(true)