diff --git a/docs/src/lib/internals/documenter.md b/docs/src/lib/internals/documenter.md
index ea7d875243..c69a8c3cd8 100644
--- a/docs/src/lib/internals/documenter.md
+++ b/docs/src/lib/internals/documenter.md
@@ -7,4 +7,5 @@ Documenter.user_host_upstream
 Documenter.find_object
 Documenter.xrefname
 Documenter.crossref
+Documenter.DocumenterBuildException
 ```
diff --git a/docs/src/lib/public.md b/docs/src/lib/public.md
index ea725bced5..7d6f94547b 100644
--- a/docs/src/lib/public.md
+++ b/docs/src/lib/public.md
@@ -31,6 +31,7 @@ doctest
 DocMeta
 DocMeta.getdocmeta
 DocMeta.setdocmeta!
+Documenter.DocumenterError
 ```
 
 ## DocumenterTools
diff --git a/src/Documenter.jl b/src/Documenter.jl
index eab6f77716..f15ae35471 100644
--- a/src/Documenter.jl
+++ b/src/Documenter.jl
@@ -65,6 +65,14 @@ abstract type Plugin end
 
 abstract type Writer end
 
+"""
+    abstract type DocumenterBuildException <: Exception
+
+Internal abstract supertype for all the exceptions that get propagated to the user as
+[`DocumenterError`](@ref)s.
+"""
+abstract type DocumenterBuildException <: Exception end
+
 include("utilities/DOM.jl")
 include("utilities/JSDependencies.jl")
 include("utilities/MDFlatten.jl")
diff --git a/src/builder_pipeline.jl b/src/builder_pipeline.jl
index af98526ae3..a3ac6003ee 100644
--- a/src/builder_pipeline.jl
+++ b/src/builder_pipeline.jl
@@ -250,15 +250,25 @@ function Selectors.runner(::Type{Builder.RenderDocument}, doc::Documenter.Docume
     fatal_errors = filter(is_strict(doc), doc.internal.errors)
     c = length(fatal_errors)
     if c > 0
-        error("`makedocs` encountered $(c > 1 ? "errors" : "an error") ["
-        * join(Ref(":") .* string.(fatal_errors), ", ")
-        * "] -- terminating build before rendering.")
+        msg = string(
+            "`makedocs` encountered $(c > 1 ? "errors" : "an error") [",
+            join(Ref(":") .* string.(fatal_errors), ", "),
+            "] -- terminating build before rendering."
+        )
+        throw(DocCheckError(msg))
     else
         @info "RenderDocument: rendering document."
         Documenter.render(doc)
     end
 end
 
+struct DocCheckError <: DocumenterBuildException
+    msg::String
+end
+function Base.showerror(io::IO, e::DocCheckError)
+    println(io, "DocCheckError: $(e.msg)")
+end
+
 Selectors.runner(::Type{Builder.DocumentPipeline}, doc::Documenter.Document) = nothing
 
 function is_doctest_only(doc, stepname)
diff --git a/src/makedocs.jl b/src/makedocs.jl
index 68aca25a0c..6b5dd70143 100644
--- a/src/makedocs.jl
+++ b/src/makedocs.jl
@@ -233,21 +233,69 @@ Other formats can be enabled by using other addon-packages. For example, the
 the original Markdown -> Markdown output. See the [Other Output Formats](@ref) for more
 information.
 
+# Errors
+
+`makedocs` will throw a [`DocumenterError`](@ref) if it has a "controlled failure", e.g. due
+document checks failing, or some other issue that is likely due to user configuration problems.
+`makedocs` throwing something other than [`DocumenterError`](@ref) should, generally be considered
+an error.
+
 # See Also
 
 A guide detailing how to document a package using Documenter's [`makedocs`](@ref) is provided
 in the [setup guide in the manual](@ref Package-Guide).
 """
 function makedocs(; debug = false, format = HTML(), kwargs...)
-    document = Documenter.Document(; format=format, kwargs...)
-    # Before starting the build pipeline, we empty out the subtype cache used by
-    # Selectors.dispatch. This is to make sure that we pick up any new selector stages that
-    # may have been added to the selector pipelines between makedocs calls.
-    empty!(Selectors.selector_subtypes)
-    cd(document.user.root) do; withenv(NO_KEY_ENV...) do
-        Selectors.dispatch(Builder.DocumentPipeline, document)
-    end end
-    debug ? document : nothing
+    exception = nothing
+    try
+        document = Documenter.Document(; format=format, kwargs...)
+        # Before starting the build pipeline, we empty out the subtype cache used by
+        # Selectors.dispatch. This is to make sure that we pick up any new selector stages that
+        # may have been added to the selector pipelines between makedocs calls.
+        empty!(Selectors.selector_subtypes)
+        cd(document.user.root) do
+            withenv(NO_KEY_ENV...) do
+                Selectors.dispatch(Builder.DocumentPipeline, document)
+            end
+        end
+        return debug ? document : nothing
+    catch e
+        if isa(e, DocumenterBuildException)
+            exc_error_log = IOBuffer()
+            showerror(exc_error_log, e, catch_backtrace())
+            @debug String(take!(exc_error_log))
+            exception = DocumenterError(:makedocs, (e, catch_backtrace()))
+        else
+            rethrow(e)
+        end
+    end
+    isnothing(exception) || throw(exception)
+end
+
+"""
+    struct DocumenterError <: Exception
+
+Documenter throws this error when it fails in a "controlled" way (e.g. when docchecks or
+doctests have failed).
+
+!!! note
+
+    Documenter is not fully consistent about using this exception yet. So while Documenter
+    throwing a different error object should be considered a bug, it may still be indicating
+    a user error (rather than Documenter itself breaking in some way).
+"""
+struct DocumenterError <: Exception
+    fn::Symbol
+    exception::Union{Tuple{Any,Any},Nothing}
+end
+
+function Base.showerror(io::IO, e::DocumenterError)
+    println(io, "DocumenterError ($(e.fn)): Documenter build failed to complete.")
+    if !isnothing(e.exception)
+        println("Underlying exception:")
+        showerror(io, e.exception[1])
+    end
+    print(io, "Please check the error logs above as well.")
 end
 
 """