diff --git a/README.md b/README.md
index 0f5658f3..95c11d47 100644
--- a/README.md
+++ b/README.md
@@ -84,3 +84,9 @@ Check [`.github/workflows/deploy.yml`](.github/workflows/deploy.yml) and [`docs/
 The result of that script is available at [https://juliacomputing.github.io/MultiDocumenter.jl/](https://juliacomputing.github.io/MultiDocumenter.jl/).
 
 You can of course also just push the output artefact directly to S3 or some other hosting service.
+
+> **Warning**
+> MultiDocumenter sites can not be deployed on Windows right now, and the `make()` function will throw an error.
+> See [#70](https://github.com/JuliaComputing/MultiDocumenter.jl/issues/70).
+>
+> It is still possible to develop and debug MultiDocumenter sites on Windows if the build script is run interactively (e.g. by `include`-ing it into a REPL session).
diff --git a/src/MultiDocumenter.jl b/src/MultiDocumenter.jl
index b1237155..f5d69232 100644
--- a/src/MultiDocumenter.jl
+++ b/src/MultiDocumenter.jl
@@ -140,7 +140,26 @@ function make(
     canonical_domain::Union{AbstractString,Nothing} = nothing,
     sitemap::Bool = false,
     sitemap_filename::AbstractString = "sitemap.xml",
+    # This keyword is for internal test use only:
+    _override_windows_isinteractive_check::Bool = false,
 )
+    if Sys.iswindows() && !isinteractive()
+        if _override_windows_isinteractive_check || isinteractive()
+            @warn """
+            Running a MultiDocumenter build interactively in Windows.
+            This should only be used for development and testing, as it will lead to partial
+            and broken builds. See https://github.com/JuliaComputing/MultiDocumenter.jl/issues/70
+            """
+        else
+            msg = """
+            MultiDocumenter deployments are disabled on Windows due to difficulties
+            with handling symlinks in documentation sources.
+            You _can_ test this build locally by running it interactively (i.e. in the REPL).
+            See also: https://github.com/JuliaComputing/MultiDocumenter.jl/issues/70
+            """
+            error(msg)
+        end
+    end
     if isnothing(canonical_domain)
         (sitemap === true) &&
             throw(ArgumentError("When sitemap=true, canonical_domain must also be set"))
@@ -249,7 +268,8 @@ function maybe_clone(docs::Vector{MultiDocRef})
                 `$(git()) clone --depth 1 $(doc.giturl) --branch $(doc.branch) --single-branch --no-tags $(doc.upstream)`,
             )
         else
-            git_dir, git_worktree = abspath(joinpath(doc.upstream, ".git")), abspath(doc.upstream)
+            git_dir, git_worktree =
+                abspath(joinpath(doc.upstream, ".git")), abspath(doc.upstream)
             if !isdir(git_dir)
                 @warn "Unable to update existing clone at $(doc.upstream): .git/ directory missing"
                 continue
@@ -266,7 +286,8 @@ function maybe_clone(docs::Vector{MultiDocRef})
             catch e
                 # We're only interested in catching `git` errors here
                 isa(e, ProcessFailedException) || rethrow()
-                @error "Unable to update existing clone at $(doc.upstream)" exception = (e, catch_backtrace())
+                @error "Unable to update existing clone at $(doc.upstream)" exception =
+                    (e, catch_backtrace())
             end
         end
     end
diff --git a/src/documentertools/canonical_urls.jl b/src/documentertools/canonical_urls.jl
index ea9ca040..fae84d0c 100644
--- a/src/documentertools/canonical_urls.jl
+++ b/src/documentertools/canonical_urls.jl
@@ -101,7 +101,9 @@ function update_canonical_links(docs_directory::AbstractString; canonical::Abstr
         # We'll skip all files. This includes files such as index.html, which in this
         # directory will likely be the redirect. Also, links should be pointing to other
         # versions, so we'll skip them too.
-        if !isdir(path) || islink(path)
+        # Note: we need to check islink() first, because on windows, calling isdir() on a
+        # symlink can make it throw a permissions IOError.
+        if islink(path) || !isdir(path)
             continue
         end
         # Preview directory is should contain other Documenter directories, so we just add
diff --git a/test/documentertools.jl b/test/documentertools.jl
index 3b44a85d..bb55b497 100644
--- a/test/documentertools.jl
+++ b/test/documentertools.jl
@@ -3,6 +3,8 @@ import MultiDocumenter: DocumenterTools
 
 FIXTURES = joinpath(@__DIR__, "fixtures")
 
+normalize_newlines(s::AbstractString) = replace(s, "\r\n" => "\n")
+
 @testset "walkdocs" begin
     let fileinfos = DocumenterTools.FileInfo[]
         rs = DocumenterTools.walkdocs(joinpath(FIXTURES, "pre")) do fileinfo
@@ -123,8 +125,8 @@ end
             canonical = "https://example.org/this-is-test",
         )
         DocumenterTools.walkdocs(joinpath(FIXTURES, "post")) do fileinfo
-            post = read(fileinfo.fullpath, String)
-            changed = read(joinpath(out, fileinfo.relpath), String)
+            post = normalize_newlines(read(fileinfo.fullpath, String))
+            changed = normalize_newlines(read(joinpath(out, fileinfo.relpath), String))
             if changed != post
                 @error "update_canonical_links: change and post not matching" out fileinfo
             end
diff --git a/test/runtests.jl b/test/runtests.jl
index 5c3b8de9..cfdae536 100644
--- a/test/runtests.jl
+++ b/test/runtests.jl
@@ -84,6 +84,30 @@ docs = [
         # giturl = "git@github.com:JuliaComputing/DataSets.jl.git",
     ),
 ]
+
+# We do not support deploying docs on Windows at the moment, and MultiDocumenter
+# should throw an error if it's being run on Windows (in a non-interactive session).
+# See also: https://github.com/JuliaComputing/MultiDocumenter.jl/issues/70
+if Sys.iswindows() && !isinteractive()
+    @test_throws ErrorException MultiDocumenter.make(
+        outpath,
+        docs;
+        search_engine = MultiDocumenter.SearchConfig(
+            index_versions = ["stable", "dev"],
+            engine = MultiDocumenter.FlexSearch,
+        ),
+        custom_scripts = [
+            "foo/bar.js",
+            "https://foo.com/bar.js",
+            Docs.HTML("const foo = 'bar';"),
+        ],
+        rootpath = rootpath,
+        canonical_domain = "https://example.org/",
+        sitemap = true,
+        sitemap_filename = "sitemap-mydocs.xml",
+    )
+end
+
 MultiDocumenter.make(
     outpath,
     docs;
@@ -100,6 +124,8 @@ MultiDocumenter.make(
     canonical_domain = "https://example.org/",
     sitemap = true,
     sitemap_filename = "sitemap-mydocs.xml",
+    # The following keyword is not standard:
+    _override_windows_isinteractive_check = Sys.iswindows(),
 )
 
 @testset "MultiDocumenter.jl" begin
@@ -107,8 +133,16 @@ MultiDocumenter.make(
     @testset "structure" begin
         @test isdir(outpath, "inf")
         @test !isdir(outpath, "inf", "previews")
-        @test isdir(outpath, "inf", "stable")
-        @test isfile(outpath, "inf", "stable", "index.html")
+        if Sys.iswindows()
+            # On Windows, symlinks are either kept as simple files, or are in fact
+            # symlinks, but then you would run into permission errors with isdir().
+            # So we need to have platform-specific test logic here.
+            path = joinpath(outpath, "inf", "stable")
+            @test islink(path) || isfile(path)
+        else
+            @test isdir(outpath, "inf", "stable")
+            @test isfile(outpath, "inf", "stable", "index.html")
+        end
 
         @test read(joinpath(outpath, "inf", "index.html"), String) == """
         <!--This file is automatically generated by Documenter.jl-->
@@ -122,8 +156,7 @@ MultiDocumenter.make(
 
 
     @testset "custom scripts" begin
-        index = read(joinpath(outpath, "inf", "stable", "index.html"), String)
-
+        index = read(joinpath(outpath, "inf", "v1.6.4", "index.html"), String)
         @test occursin(
             """<script charset="utf-8" type="text/javascript">window.MULTIDOCUMENTER_ROOT_PATH = '$rootpath'</script>""",
             index,
@@ -140,12 +173,36 @@ MultiDocumenter.make(
             """<script charset="utf-8" type="text/javascript">const foo = 'bar';</script>""",
             index,
         )
+
+        if !Sys.iswindows()
+            # Going through symlinks does not work on Windows
+            index = read(joinpath(outpath, "inf", "stable", "index.html"), String)
+            @test occursin(
+                """<script charset="utf-8" type="text/javascript">window.MULTIDOCUMENTER_ROOT_PATH = '$rootpath'</script>""",
+                index,
+            )
+            @test occursin(
+                """<script charset="utf-8" src="../../foo/bar.js" type="text/javascript"></script>""",
+                index,
+            )
+            @test occursin(
+                """<script charset="utf-8" src="https://foo.com/bar.js" type="text/javascript"></script>""",
+                index,
+            )
+            @test occursin(
+                """<script charset="utf-8" type="text/javascript">const foo = 'bar';</script>""",
+                index,
+            )
+        end
     end
 
     @testset "canonical URLs" begin
-        index = read(joinpath(outpath, "inf", "stable", "index.html"), String)
-        canonical_href = "<link href=\"https://example.org/MultiDocumenter.jl/inf/stable/\" rel=\"canonical\"/>"
-        @test occursin(canonical_href, index)
+        # We can't traverse symlinks on Windows, so we ignore this case
+        if !Sys.iswindows()
+            index = read(joinpath(outpath, "inf", "stable", "index.html"), String)
+            canonical_href = "<link href=\"https://example.org/MultiDocumenter.jl/inf/stable/\" rel=\"canonical\"/>"
+            @test occursin(canonical_href, index)
+        end
 
         index = read(joinpath(outpath, "inf", "v1.6.0", "index.html"), String)
         canonical_href = "<link href=\"https://example.org/MultiDocumenter.jl/inf/stable/\" rel=\"canonical\"/>"
@@ -158,9 +215,17 @@ MultiDocumenter.make(
         @test !isempty(store_content)
         @test occursin("Infiltrator.jl", store_content)
         @test occursin("@infiltrate", store_content)
-        @test occursin("$(rootpath)inf/stable/", store_content)
-        @test occursin("$(rootpath)inf/stable/", store_content)
-        @test !occursin("/inf/dev/", store_content)
+        # We can't traverse symlinks on Windows, so stable/ things do not get
+        # written into the search index. Instead, it looks like we write dev/
+        if Sys.iswindows()
+            @test !occursin("$(rootpath)inf/stable/", store_content)
+            @test !occursin("$(rootpath)inf/stable/", store_content)
+            @test occursin("/inf/dev/", store_content)
+        else
+            @test occursin("$(rootpath)inf/stable/", store_content)
+            @test occursin("$(rootpath)inf/stable/", store_content)
+            @test !occursin("/inf/dev/", store_content)
+        end
     end
 
     @testset "sitemap" begin