I want the following inequality hold: $$ (\xi_1a_1+\xi_2a_2+\xi_3a_3)(a_4+a_5+a_6) < (a_1+a_2+a_3)(\eta_1a_4+\eta_2a_5+\eta_3a_6) $$ where $a_1, ..., a_6>0$ and $0 \leq \xi_i < \eta_i$ for $i=1,2,3$.
Is this inequality true or false, and when this inequality can be guaranteed to hold? Any suggestions?
Not necessarily true, as in there are $a_1,\ldots, a_6$ and $\xi_1,\xi_2, \xi_3$ and $\eta_1,\eta_2,\eta_3$ that meet the conditions of your hypothesis and yet the (strict) inequality $(\xi_1a_1+\xi_2a_2+\xi_3a_3)(a_4+a_5+a_6) > (a_1+a_2+a_3)(\eta_1 a_4+\eta_2 a_5 +\eta_3 a_6)$ holds.
Suppose
$a_1=a_4=a_5=a_6 =1$ and $a_2=a_3 = \epsilon$
$\xi_1 = (1-\delta)$ for some small $\delta >0$; $\xi_2=\xi_3 = \epsilon$ for some small $\epsilon >0$
$\eta_1=1$, $\eta_2=\eta_3= 2\epsilon$.
Then the conditions of your hypothesis are met.
However, $(\xi_1a_1+\xi_2a_2+\xi_3a_3)(a_4+a_5+a_6) \ge 2.75$ if $\delta <.1$
Yet $(a_1+a_2+a_3)(\eta_1 a_4+\eta_2 a_5 +\eta_3 a_6) \le 1.25$ if $\epsilon < .1$.