diff --git a/CHANGELOG.md b/CHANGELOG.md
index 19e4773e063..9547ae04bd8 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,6 +10,8 @@
 
 * ![Enhancement][badge-enhancement] If the TeX compilation fails for the PDF/LaTeX output, `makedocs` now throws an exception. ([#1166](github-1166))
 
+* ![Bugfix][badge-bugfix] `LaTeXWriter` now outputs valid LaTeX if an `@contents` block is nested by more than two levels, or if `@contents` or `@index` blocks do not contain any items. ([#1166](github-1166))
+
 * ![BREAKING][badge-breaking] Documenter no longer creates a symlink between the old `latest` url to specified `devurl`. Make sure to update links in e.g. the package readme. ([#1151][github-1151])
 
 ## Version `v0.23.4`
diff --git a/src/Writers/LaTeXWriter.jl b/src/Writers/LaTeXWriter.jl
index 8ca7eaceafe..de3137c9619 100644
--- a/src/Writers/LaTeXWriter.jl
+++ b/src/Writers/LaTeXWriter.jl
@@ -140,7 +140,9 @@ function render(doc::Documents.Document, settings::LaTeX=LaTeX())
             # Debug: if DOCUMENTER_LATEX_DEBUG environment variable is set, copy the LaTeX
             # source files over to a directory under doc.user.root.
             if haskey(ENV, "DOCUMENTER_LATEX_DEBUG")
-                sources = cp(pwd(), mktempdir(doc.user.root), force=true)
+                dst = isempty(ENV["DOCUMENTER_LATEX_DEBUG"]) ? mktempdir(doc.user.root) :
+                    joinpath(doc.user.root, ENV["DOCUMENTER_LATEX_DEBUG"])
+                sources = cp(pwd(), dst, force=true)
                 @info "LaTeX sources copied for debugging to $(sources)"
             end
 
@@ -303,6 +305,10 @@ end
 ## Index, Contents, and Eval Nodes.
 
 function latex(io::IO, index::Documents.IndexNode, page, doc)
+    # Having an empty itemize block in LaTeX throws an error, so we bail early
+    # in that situation:
+    isempty(index.elements) && (_println(io); return)
+
     _println(io, "\\begin{itemize}")
     for (object, _, page, mod, cat) in index.elements
         id = string(hash(string(Utilities.slugify(object))))
@@ -316,22 +322,40 @@ function latex(io::IO, index::Documents.IndexNode, page, doc)
 end
 
 function latex(io::IO, contents::Documents.ContentsNode, page, doc)
+    # Having an empty itemize block in LaTeX throws an error, so we bail early
+    # in that situation:
+    isempty(contents.elements) && (_println(io); return)
+
     depth = 1
-    needs_end = false
     _println(io, "\\begin{itemize}")
     for (count, path, anchor) in contents.elements
         header = anchor.object
         level = Utilities.header_level(header)
         id = string(hash(string(anchor.id, "-", anchor.nth)))
-        level < depth && (_println(io, "\\end{itemize}"); needs_end = false)
-        level > depth && (_println(io, "\\begin{itemize}"); needs_end = true)
+        # If we're changing depth, we need to make sure we always print the
+        # correct number of \begin{itemize} and \end{itemize} statements.
+        if level > depth
+            for k in 1:(level - depth)
+                # if we jump by more than one level deeper we need to put empty
+                # \items in -- otherwise LaTeX will complain
+                (k >= 2) && _println(io, "\\item ~")
+                _println(io, "\\begin{itemize}")
+                depth += 1
+            end
+        elseif level < depth
+            for _ in 1:(depth - level)
+                _println(io, "\\end{itemize}")
+                depth -= 1
+            end
+        end
+        # Print the corresponding \item statement
         _print(io, "\\item \\hyperlink{", id, "}{")
         latexinline(io, header.text)
         _println(io, "}")
-        depth = level
+        @assert depth == level
     end
-    needs_end && _println(io, "\\end{itemize}")
-    _println(io, "\\end{itemize}")
+    # print any remaining missing \end{itemize} statements
+    for _ = 1:depth; _println(io, "\\end{itemize}"); end
     _println(io)
 end
 
diff --git a/test/examples/make.jl b/test/examples/make.jl
index 672943858eb..6628b04cff0 100644
--- a/test/examples/make.jl
+++ b/test/examples/make.jl
@@ -160,6 +160,7 @@ htmlbuild_pages = Any[
         "expandorder/AA.md",
     ],
     "unicode.md",
+    "latex.md",
 ]
 
 # Build with pretty URLs and canonical links and a PNG logo
@@ -260,6 +261,46 @@ else
     nothing
 end
 
+examples_latex_doc = if "latex" in EXAMPLE_BUILDS
+    @info("Building mock package docs: LaTeXWriter/latex")
+    @quietly makedocs(
+        format = Documenter.Writers.LaTeXWriter.LaTeX(platform = "docker"),
+        sitename = "Documenter LaTeX",
+        root  = examples_root,
+        build = "builds/latex",
+        pages = htmlbuild_pages = Any[
+            "General" => [
+                "index.md",
+                "latex.md",
+                "unicode.md",
+                hide("hidden.md"),
+            ],
+            # man/tutorial.md can't be built because it contains SVG images
+            # "Manual" => ["man/tutorial.md"],
+            hide("Hidden Pages" => "hidden/index.md", Any[
+                "Page X" => "hidden/x.md",
+                "hidden/y.md",
+                "hidden/z.md",
+            ]),
+            "Library" => [
+                "lib/functions.md",
+                "lib/autodocs.md",
+                "lib/editurl.md",
+            ],
+            "Expandorder" => [
+                "expandorder/00.md",
+                "expandorder/01.md",
+                "expandorder/AA.md",
+            ],
+        ],
+        doctest = false,
+        debug = true,
+    )
+else
+    @info "Skipping build: LaTeXWriter/latex" EXAMPLE_BUILDS get(ENV, "DOCUMENTER_TEST_EXAMPLES", nothing)
+    nothing
+end
+
 examples_latex_simple_nondocker_doc = if "latex_simple_nondocker" in EXAMPLE_BUILDS
     @info("Building mock package docs: LaTeXWriter/latex_simple_nondocker")
     @quietly makedocs(
diff --git a/test/examples/src/latex.md b/test/examples/src/latex.md
new file mode 100644
index 00000000000..be5b7ef6d69
--- /dev/null
+++ b/test/examples/src/latex.md
@@ -0,0 +1,22 @@
+# LaTeX MWEs
+
+## `ContentsNode` level jumps
+
+```@contents
+Pages = ["latex.md"]
+Depth = 9000
+```
+
+#### Level 4
+## Level 2 again
+### Level 3
+
+## Empty `ContentsNode` and `IndexNode`
+
+```@contents
+Pages = ["does-not-exist.md"]
+```
+
+```@index
+Pages = ["does-not-exist.md"]
+```
diff --git a/test/examples/tests_latex.jl b/test/examples/tests_latex.jl
index a4925923dd4..cd7ff59c765 100644
--- a/test/examples/tests_latex.jl
+++ b/test/examples/tests_latex.jl
@@ -24,4 +24,12 @@ end
             @test joinpath(build_dir, "DocumenterLaTeXSimple.pdf") |> isfile
         end
     end
+
+    @testset "PDF/LaTeX" begin
+        doc = Main.examples_latex_doc
+        @test isa(doc, Documenter.Documents.Document)
+        let build_dir = joinpath(examples_root, "builds", "latex")
+            @test joinpath(build_dir, "DocumenterLaTeX.pdf") |> isfile
+        end
+    end
 end