diff --git a/compiler/rustc_hir_typeck/src/expr.rs b/compiler/rustc_hir_typeck/src/expr.rs
index 6ebf382083f25..10e1d3bdc5e1b 100644
--- a/compiler/rustc_hir_typeck/src/expr.rs
+++ b/compiler/rustc_hir_typeck/src/expr.rs
@@ -421,23 +421,34 @@ impl<'a, 'tcx> FnCtxt<'a, 'tcx> {
             return Ty::new_error(tcx, guar);
         }
 
-        let oprnd_t = self.structurally_resolve_type(expr.span, oprnd_t);
+        // `Not` and `Neg` can be selected using an unresolved operand type,
+        // later constraints may still determine that type,
+        // so we call `resolve_vars_with_obligations` for them.
         match unop {
-            hir::UnOp::Deref => self.lookup_derefing(expr, oprnd, oprnd_t).unwrap_or_else(|| {
-                let mut err =
-                    self.dcx().create_err(CantDereference { span: expr.span, ty: oprnd_t });
-                let sp = tcx.sess.source_map().start_point(expr.span).with_parent(None);
-                if let Some(sp) = tcx.sess.psess.ambiguous_block_expr_parse.borrow().get(&sp) {
-                    err.subdiagnostic(ExprParenthesesNeeded::surrounding(*sp));
-                }
-                Ty::new_error(tcx, err.emit())
-            }),
+            hir::UnOp::Deref => {
+                // Dereferencing must distinguish builtin pointers from
+                // overloaded `Deref`, so it still requires a structurally resolved type.
+                //
+                // This is necessary as raw pointers do not implement `Deref`.
+                let oprnd_t = self.structurally_resolve_type(expr.span, oprnd_t);
+                self.lookup_derefing(expr, oprnd, oprnd_t).unwrap_or_else(|| {
+                    let mut err =
+                        self.dcx().create_err(CantDereference { span: expr.span, ty: oprnd_t });
+                    let sp = tcx.sess.source_map().start_point(expr.span).with_parent(None);
+                    if let Some(sp) = tcx.sess.psess.ambiguous_block_expr_parse.borrow().get(&sp) {
+                        err.subdiagnostic(ExprParenthesesNeeded::surrounding(*sp));
+                    }
+                    Ty::new_error(tcx, err.emit())
+                })
+            }
             hir::UnOp::Not => {
+                let oprnd_t = self.resolve_vars_with_obligations(oprnd_t);
                 let result = self.check_user_unop(expr, oprnd_t, unop, expected_inner);
                 // If it's builtin, we can reuse the type, this helps inference.
                 if oprnd_t.is_integral() || *oprnd_t.kind() == ty::Bool { oprnd_t } else { result }
             }
             hir::UnOp::Neg => {
+                let oprnd_t = self.resolve_vars_with_obligations(oprnd_t);
                 let result = self.check_user_unop(expr, oprnd_t, unop, expected_inner);
                 // If it's builtin, we can reuse the type, this helps inference.
                 if oprnd_t.is_numeric() { oprnd_t } else { result }
diff --git a/tests/ui/inference/unary-deref-late-raw-pointer-inference-issue-106138.rs b/tests/ui/inference/unary-deref-late-raw-pointer-inference-issue-106138.rs
new file mode 100644
index 0000000000000..c2d67e02ed520
--- /dev/null
+++ b/tests/ui/inference/unary-deref-late-raw-pointer-inference-issue-106138.rs
@@ -0,0 +1,14 @@
+//! Regression test for https://github.com/rust-lang/rust/issues/106138.
+//! An unresolved dereference must not treat a raw pointer as an overloaded `Deref`.
+
+fn make<T>() -> T {
+    loop {}
+}
+
+fn main() {
+    let pointer = make();
+    //~^ ERROR type annotations needed
+    let value = unsafe { *pointer };
+    let _: *const u8 = pointer;
+    let _: u8 = value;
+}
diff --git a/tests/ui/inference/unary-deref-late-raw-pointer-inference-issue-106138.stderr b/tests/ui/inference/unary-deref-late-raw-pointer-inference-issue-106138.stderr
new file mode 100644
index 0000000000000..f6a2a772ffe54
--- /dev/null
+++ b/tests/ui/inference/unary-deref-late-raw-pointer-inference-issue-106138.stderr
@@ -0,0 +1,17 @@
+error[E0282]: type annotations needed
+  --> $DIR/unary-deref-late-raw-pointer-inference-issue-106138.rs:9:9
+   |
+LL |     let pointer = make();
+   |         ^^^^^^^
+LL |
+LL |     let value = unsafe { *pointer };
+   |                          -------- type must be known at this point
+   |
+help: consider giving `pointer` an explicit type
+   |
+LL |     let pointer: /* Type */ = make();
+   |                ++++++++++++
+
+error: aborting due to 1 previous error
+
+For more information about this error, try `rustc --explain E0282`.
diff --git a/tests/ui/inference/unary-neg-late-operand-inference-issue-26830.rs b/tests/ui/inference/unary-neg-late-operand-inference-issue-26830.rs
new file mode 100644
index 0000000000000..9f2ad98e5d6b4
--- /dev/null
+++ b/tests/ui/inference/unary-neg-late-operand-inference-issue-26830.rs
@@ -0,0 +1,27 @@
+//! Regression test for https://github.com/rust-lang/rust/issues/26830.
+//! Unary negation should allow later constraints to determine its operand type.
+
+//@ check-pass
+
+fn make<T>() -> T {
+    loop {}
+}
+
+fn constrained_by_value() {
+    let input = make();
+    let output = -input;
+    let _: i32 = input;
+    let _: i32 = output;
+}
+
+fn constrained_by_borrow() {
+    let input = make();
+    let output = -input;
+    let _: &i32 = &input;
+    let _: i32 = output;
+}
+
+fn main() {
+    constrained_by_value();
+    constrained_by_borrow();
+}
diff --git a/tests/ui/inference/unary-op-associated-output-mismatch-issue-106138.rs b/tests/ui/inference/unary-op-associated-output-mismatch-issue-106138.rs
new file mode 100644
index 0000000000000..b30535115602e
--- /dev/null
+++ b/tests/ui/inference/unary-op-associated-output-mismatch-issue-106138.rs
@@ -0,0 +1,42 @@
+//! Regression test for https://github.com/rust-lang/rust/issues/106138.
+//! From comment https://github.com/rust-lang/rust/pull/107567#discussion_r1093589448
+//! Unary operator inference must not assume that the associated output type equals `Self`.
+
+#[derive(Copy, Clone, Default)]
+struct A;
+
+struct B;
+
+impl std::ops::Not for A {
+    type Output = B;
+
+    fn not(self) -> B {
+        B
+    }
+}
+
+#[derive(Copy, Clone)]
+struct NoNot;
+
+fn make<T>() -> T {
+    loop {}
+}
+
+fn resolved_without_impl() {
+    let value = make();
+    let _ = !value;
+    //~^ ERROR the trait bound `NoNot: Not` is not satisfied
+    let _: NoNot = value;
+}
+
+fn unconstrained() {
+    let value = make();
+    //~^ ERROR type annotations needed
+    let _ = !value;
+}
+
+fn main() {
+    let x = Default::default();
+    //~^ ERROR cannot call associated function on trait
+    let _: A = !x;
+}
diff --git a/tests/ui/inference/unary-op-associated-output-mismatch-issue-106138.stderr b/tests/ui/inference/unary-op-associated-output-mismatch-issue-106138.stderr
new file mode 100644
index 0000000000000..30318239390e5
--- /dev/null
+++ b/tests/ui/inference/unary-op-associated-output-mismatch-issue-106138.stderr
@@ -0,0 +1,43 @@
+error[E0277]: the trait bound `NoNot: Not` is not satisfied
+  --> $DIR/unary-op-associated-output-mismatch-issue-106138.rs:27:13
+   |
+LL |     let _ = !value;
+   |             ^^^^^^ unsatisfied trait bound
+   |
+help: the trait `Not` is not implemented for `NoNot`
+  --> $DIR/unary-op-associated-output-mismatch-issue-106138.rs:19:1
+   |
+LL | struct NoNot;
+   | ^^^^^^^^^^^^
+
+error[E0284]: type annotations needed
+  --> $DIR/unary-op-associated-output-mismatch-issue-106138.rs:33:9
+   |
+LL |     let value = make();
+   |         ^^^^^
+LL |
+LL |     let _ = !value;
+   |             ------ type must be known at this point
+   |
+   = note: cannot satisfy `<_ as Not>::Output == _`
+   = note: the type must also implement `Not`
+help: consider giving `value` an explicit type
+   |
+LL |     let value: /* Type */ = make();
+   |              ++++++++++++
+
+error[E0790]: cannot call associated function on trait without specifying the corresponding `impl` type
+  --> $DIR/unary-op-associated-output-mismatch-issue-106138.rs:39:13
+   |
+LL |     let x = Default::default();
+   |             ^^^^^^^^^^^^^^^^^^ cannot call associated function of trait
+   |
+help: use a fully-qualified path to a specific available implementation
+   |
+LL |     let x = </* self type */ as Default>::default();
+   |             +++++++++++++++++++        +
+
+error: aborting due to 3 previous errors
+
+Some errors have detailed explanations: E0277, E0284, E0790.
+For more information about an error, try `rustc --explain E0277`.
diff --git a/tests/ui/inference/unary-op-late-operand-inference-issue-106138.rs b/tests/ui/inference/unary-op-late-operand-inference-issue-106138.rs
new file mode 100644
index 0000000000000..549c7a91d6f00
--- /dev/null
+++ b/tests/ui/inference/unary-op-late-operand-inference-issue-106138.rs
@@ -0,0 +1,49 @@
+//! Regression test for https://github.com/rust-lang/rust/issues/106138.
+//! Unary operators should allow their operand types to be inferred by later constraints.
+
+//@ check-pass
+
+use std::ops::Not;
+
+fn not_index(x: &Vec<bool>) {
+    let closure = |i, a: &Vec<bool>| !a[i];
+    let _ = closure(0, x);
+}
+
+fn neg_index(x: &Vec<i32>) {
+    let closure = |i, a: &Vec<i32>| -a[i];
+    let _ = closure(0, x);
+}
+
+#[derive(Copy, Clone, Default)]
+struct Input;
+
+struct Output;
+
+impl Not for Input {
+    type Output = Output;
+
+    fn not(self) -> Self::Output {
+        Output
+    }
+}
+
+fn output_differs_from_operand() {
+    let input = Default::default();
+    let output = !input;
+    let _: Input = input;
+    let _: Output = output;
+}
+
+fn output_expectation_differs_from_operand() {
+    let input = Default::default();
+    let _: Output = !input;
+    let _: Input = input;
+}
+
+fn main() {
+    not_index(&vec![true]);
+    neg_index(&vec![1]);
+    output_differs_from_operand();
+    output_expectation_differs_from_operand();
+}