diff --git a/src/pkgs.jl b/src/pkgs.jl
index ae294e23..17a2ec87 100644
--- a/src/pkgs.jl
+++ b/src/pkgs.jl
@@ -332,7 +332,21 @@ function add_require(sourcefile, modcaller, idmod, modname, expr)
         exsnew = ExprsSigs()
         exsnew[expr] = nothing
         mexsnew = ModuleExprsSigs(modcaller=>exsnew)
-        mexsnew, includes = eval_new!(mexsnew, fi.modexsigs)
+        # Before executing the expression we need to set the load path appropriately
+        prev = Base.source_path(nothing)
+        tls = task_local_storage()
+        tls[:SOURCE_PATH] = sourcefile
+        # Now execute the expression
+        mexsnew, includes = try
+            eval_new!(mexsnew, fi.modexsigs)
+        finally
+            if prev === nothing
+                delete!(tls, :SOURCE_PATH)
+            else
+                tls[:SOURCE_PATH] = prev
+            end
+        end
+        # Add any new methods or `include`d files to tracked objects
         pkgdata.fileinfos[fileidx] = FileInfo(mexsnew, fi)
         maybe_add_includes_to_pkgdata!(pkgdata, filekey, includes)
     end
diff --git a/test/pkgs/Dep442A/Project.toml b/test/pkgs/Dep442A/Project.toml
new file mode 100644
index 00000000..eb42e8c6
--- /dev/null
+++ b/test/pkgs/Dep442A/Project.toml
@@ -0,0 +1,4 @@
+name = "Dep442A"
+uuid = "76238f47-ed95-4e4a-a4d9-95a3fb1630ea"
+authors = ["Tim Holy <tim.holy@gmail.com>"]
+version = "0.1.0"
diff --git a/test/pkgs/Dep442A/src/Dep442A.jl b/test/pkgs/Dep442A/src/Dep442A.jl
new file mode 100644
index 00000000..6989bba6
--- /dev/null
+++ b/test/pkgs/Dep442A/src/Dep442A.jl
@@ -0,0 +1,7 @@
+module Dep442A
+
+export check442A
+
+check442A() = true
+
+end # module
diff --git a/test/pkgs/Dep442B/Project.toml b/test/pkgs/Dep442B/Project.toml
new file mode 100644
index 00000000..038e2192
--- /dev/null
+++ b/test/pkgs/Dep442B/Project.toml
@@ -0,0 +1,7 @@
+name = "Dep442B"
+uuid = "880097ba-c503-4edb-bd3f-4c6394f19e96"
+authors = ["Tim Holy <tim.holy@gmail.com>"]
+version = "0.1.0"
+
+[deps]
+Requires = "ae029012-a4dd-5104-9daa-d747884805df"
diff --git a/test/pkgs/Dep442B/src/Dep442B.jl b/test/pkgs/Dep442B/src/Dep442B.jl
new file mode 100644
index 00000000..7241444d
--- /dev/null
+++ b/test/pkgs/Dep442B/src/Dep442B.jl
@@ -0,0 +1,18 @@
+module Dep442B
+
+using Requires
+
+export check442B
+
+check442B() = true
+
+function link_442A()
+    @debug "Loading 442A support into 442B"
+    include("support_442A.jl")
+end
+
+function __init__()
+    @require Dep442A="76238f47-ed95-4e4a-a4d9-95a3fb1630ea" link_442A()
+end
+
+end # module
diff --git a/test/pkgs/Dep442B/src/support_442A.jl b/test/pkgs/Dep442B/src/support_442A.jl
new file mode 100644
index 00000000..4ceac6a4
--- /dev/null
+++ b/test/pkgs/Dep442B/src/support_442A.jl
@@ -0,0 +1 @@
+has442A() = true
diff --git a/test/pkgs/Pkg442/Project.toml b/test/pkgs/Pkg442/Project.toml
new file mode 100644
index 00000000..a42619fe
--- /dev/null
+++ b/test/pkgs/Pkg442/Project.toml
@@ -0,0 +1,8 @@
+name = "Pkg442"
+uuid = "753a5fd8-985c-4be4-bc89-999c80d1e0e5"
+authors = ["Tim Holy <tim.holy@gmail.com>"]
+version = "0.1.0"
+
+[deps]
+Dep442A = "76238f47-ed95-4e4a-a4d9-95a3fb1630ea"
+Dep442B = "880097ba-c503-4edb-bd3f-4c6394f19e96"
diff --git a/test/pkgs/Pkg442/src/Pkg442.jl b/test/pkgs/Pkg442/src/Pkg442.jl
new file mode 100644
index 00000000..8dbca00d
--- /dev/null
+++ b/test/pkgs/Pkg442/src/Pkg442.jl
@@ -0,0 +1,10 @@
+module Pkg442
+
+using Dep442A
+using Dep442B
+
+export check442
+
+check442() = true
+
+end # module
diff --git a/test/runtests.jl b/test/runtests.jl
index d9a2cb4e..83b1aaf7 100644
--- a/test/runtests.jl
+++ b/test/runtests.jl
@@ -2722,6 +2722,16 @@ do_test("New files & Requires.jl") && @testset "New files & Requires.jl" begin
     yry()
     notified && @test TrackRequires2.othertestfunc() == -2
 
+    # Issue #442
+    push!(LOAD_PATH, joinpath(@__DIR__, "pkgs"))
+    @eval using Pkg442
+    sleep(0.01)
+    @test check442()
+    @test Pkg442.check442A()
+    @test Pkg442.check442B()
+    @test Pkg442.Dep442B.has442A()
+    pop!(LOAD_PATH)
+
     rm_precompile("TrackRequires")
     rm_precompile("TrackRequires2")
     pop!(LOAD_PATH)